{"id":31885,"date":"2020-05-27T08:10:39","date_gmt":"2020-05-27T00:10:39","guid":{"rendered":"\/\/www.gsbet888.com\/?p=31885"},"modified":"2020-05-26T06:17:31","modified_gmt":"2020-05-25T22:17:31","slug":"caglioti-%e5%8f%8d%e5%ba%94","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2020\/05\/caglioti-%e5%8f%8d%e5%ba%94.html","title":{"rendered":"Caglioti \u53cd\u5e94"},"content":{"rendered":"<h4><strong>\u6982\u8981<\/strong><\/h4>\n<p>Caglioti\u53cd\u5e94 (Caglioti reaction)\u662f\u5c06\u919b\u3001\u916e\u6216\u4e0e\u5176\u76f8\u5bf9\u5e94\u7684\u5bf9\u7532\u82ef\u78fa\u9170\u8159\u5728\u6c22\u5316\u7269 (\u5982NaBH<sub>4<\/sub>, LiAlH<sub>4<\/sub>, NaBH<sub>3<\/sub>CN, B<sub>2<\/sub>H<sub>6<\/sub>\u7b49)\u4f5c\u7528\u4e0b\uff0c\u751f\u6210\u70f7\u70c3\u6216\u70ef\u70c3 (\u5bf9\u4e8e\u03b1, \u03b2-\u4e0d\u9971\u548c\u919b\u53ca\u916e)\u7684\u53cd\u5e94\uff0c\u53c8\u79f0\u4e3aCaglioti\u8fd8\u539f (Caglioti reduction)\u6216Caglioti\u70ef\u70c3\u5408\u6210 (Caglioti alkene synthesis)<sup> [1]-[6]<\/sup>\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/1-1.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31886 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/1-1.jpg\" alt=\"\" width=\"674\" height=\"734\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/1-1.jpg 810w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/1-1-276x300.jpg 276w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/1-1-680x740.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/1-1-768x836.jpg 768w\" sizes=\"(max-width: 674px) 100vw, 674px\" \/><\/a><\/p>\n<p>\u8be5\u53cd\u5e94\u7531\u610f\u5927\u5229\u901a\u7528\u5316\u5b66\u7814\u7a76\u6240 (Istituto di Chimica Generale)\u7684L. Caglioti\u57281962\u5e74\u9996\u6b21\u62a5\u9053<sup>[1]<\/sup>\u3002\u8be5\u65b9\u6cd5\u4e2d\uff0c\u76ee\u6807\u4ea7\u7269\u70f7\u70c3 (\u53ef\u4f5c\u4e3aWolff-Kishner\u8fd8\u539f, Wolff-Kishner\u8fd8\u539fHuang-Minlon\u6539\u8fdb\u6cd5\u53caClemmensen\u8fd8\u539f\u7684\u6709\u6548\u66ff\u4ee3\u65b9\u6cd5)\u6216\u70ef\u70c3\u4ea7\u7269\u4ea7\u7387\u826f\u597d\u3002\u7136\u800c\uff0c\u53cd\u5e94\u6761\u4ef6\u8f83\u4e3a\u82db\u523b\uff0c\u4f8b\u5982\uff0c\u5728\u91c7\u7528\u787c\u70f7\/\u4e59\u9178\u9150\u4f53\u7cfb\u65f6\uff0c\u53cd\u5e94\u76f8\u4f9d\u5341\u5206\u4e25\u683c\u7684\u65e0\u6c34\u65e0\u6c27\u6761\u4ef6\uff0c\u800c\u4e14\uff0c\u8fd8\u539f\u5242\u7528\u91cf\u8f83\u5927\uff0c\u5728\u53cd\u5e94\u8fc7\u7a0b\u4e2d\u4f1a\u4f7f\u90e8\u5206\u5e95\u7269\u51fa\u73b0\u8f83\u591a\u7684\u526f\u53cd\u5e94<sup>[3]<\/sup>\u3002\u53e6\u5916\uff0c\u91c7\u7528\u6c22\u5316\u94dd\u9502\u65f6\uff0c\u53cd\u5e94\u8fc7\u7a0b\u4e2d\uff0c\u5316\u5b66\u9009\u62e9\u6027\u53ca\u5b98\u80fd\u56e2\u517c\u5bb9\u6027\u53ef\u80fd\u8f83\u5dee\uff0c\u5e95\u7269\u9002\u7528\u8303\u56f4\u8f83\u4e3a\u6709\u9650<sup>[7]<\/sup>\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/2-1.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31887 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/2-1.jpg\" alt=\"\" width=\"656\" height=\"521\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/2-1.jpg 1042w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/2-1-300x238.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/2-1-680x540.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/2-1-768x610.jpg 768w\" sizes=\"(max-width: 656px) 100vw, 656px\" \/><\/a><\/p>\n<p>\u4e3a\u89e3\u51b3\u8fd9\u4e9b\u95ee\u9898\uff0c1975\u5e74Kabalka\u8bfe\u9898\u7ec4\u7814\u7a76\u53d1\u73b0\uff0c\u91c7\u7528\u513f\u8336\u915a\u787c\u70f7 (catecholborane)\uff0c\u80fd\u591f\u4f7f\u53cd\u5e94\u6761\u4ef6\u66f4\u52a0\u6e29\u548c\uff0c\u8bd5\u5242\u7528\u91cf\u53ca\u526f\u53cd\u5e94\u5927\u4e3a\u51cf\u5c11\u3002\u540c\u65f6\uff0c\u5177\u6709\u66f4\u52a0\u4f18\u826f\u7684\u4ea7\u7387\u53ca\u5b98\u80fd\u56e2\u517c\u5bb9\u6027<sup>[8]-[9]<\/sup>\u3002\u6587\u732e\u4e2d\u5c06\u8fd9\u79cd\u6539\u8fdb\u7684Caglioti\u53cd\u5e94\u79f0\u4e3aKabalka\u6539\u8fdb\u6cd5 (Kabalka modification)\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/3-1.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31888 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/3-1.jpg\" alt=\"\" width=\"659\" height=\"275\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/3-1.jpg 1069w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/3-1-300x125.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/3-1-680x284.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/3-1-768x320.jpg 768w\" sizes=\"(max-width: 659px) 100vw, 659px\" \/><\/a><\/p>\n<p>\u76ee\u524d\uff0c\u8be5\u53cd\u5e94\u5df2\u6210\u4e3a\u6709\u673a\u5408\u6210\u8fc7\u7a0b\u4e2d\u5f15\u5165\u70f7\u70c3\u6216\u70ef\u70c3\u5355\u5143\u7684\u6709\u6548\u65b9\u6cd5\uff0c\u5728\u590d\u6742\u6709\u673a\u5206\u5b50\u5408\u6210\u8bbe\u8ba1\u53ca\u5929\u7136\u4ea7\u7269\u5168\u5408\u6210\u8fc7\u7a0b\u4e2d\u6709\u6f5c\u5728\u7684\u5e94\u7528\u4ef7\u503c<sup>[10]-[12]<\/sup>\u3002<\/p>\n<h4><strong>\u57fa\u672c\u6587\u732e<\/strong><\/h4>\n<ul>\n<li>[1] L. Caglioti, M. Magi, Tetrahedron Lett. 1962, 18, 1261. doi: <a href=\"https:\/\/doi.org\/10.1016\/S0040-4039(00)62045-2\">10.1016\/S0040-4039(00)62045-2<\/a>..<\/li>\n<li>[2] L. Caglioti, M. Magi, Tetrahedron 1963, 19, 1127. doi: <a href=\"https:\/\/doi.org\/10.1016\/S0040-4020(01)98571-0\">10.1016\/S0040-4020(01)98571-0<\/a>.<\/li>\n<li>[3] R. C. Cambie, P. S. Rutledge, D. W. Scott, P. D. Woodgate, Aust. J. Chem. 1979, 32, 695. doi: <a href=\"https:\/\/www.publish.csiro.au\/ch\/CH9790695\">10.1071\/CH9790695.<\/a><\/li>\n<li>[4] R. O. Hutchins, C. A. Milewski, B. E. Maryanoff, J. Am. Chem. Soc. 1973, 95, 3662. doi: <a href=\"https:\/\/doi.org\/10.1021\/ja00792a033\">10.1021\/ja00792a033<\/a>.<\/li>\n<li>[5] R. O. Hutchins, B. E. Maryanoff, C. A. Milewski, J. Am. Chem. Soc. 1971, 93, 1793. doi: <a href=\"https:\/\/doi.org\/10.1021\/ja00736a044\">10.1021\/ja00736a044<\/a>.<\/li>\n<li>[6] S. Cacchi, L. Caglioti, G. Paolucci, Bull. Chem. Soc. Jpn.1974, 47, 2323. doi: <a href=\"https:\/\/doi.org\/10.1246\/bcsj.47.2323\">10.1246\/bcsj.47.2323<\/a>.<\/li>\n<li>[7] R. Ballini, M. Petrini, G. Rosini, J. Org. Chem. 1990, 55, 5159. doi: <a href=\"https:\/\/doi.org\/10.1021\/jo00304a032\">10.1021\/jo00304a032<\/a>.<\/li>\n<li>[8] G. W. Kabalka, J. D. Baker Jr, J. Org. Chem. 1975, 40, 1834. doi: <a href=\"https:\/\/doi.org\/10.1021\/jo00900a033\">10.1021\/jo00900a033<\/a>.<\/li>\n<li>[9] G. W. Kabalka, D. T. C. Yang, J. D. Baker, J. Org. Chem. 1976, 41, 574. doi: <a href=\"https:\/\/doi.org\/10.1021\/jo00865a043\">10.1021\/jo00865a043<\/a>.<\/li>\n<li>[10] P. Camps, G. Colet, S. Segura, S. V\u00e1zquez, ARKIVOC 2007, (iv) 8. doi: <a href=\"https:\/\/doi.org\/10.3998\/ark.5550190.0008.402\">10.3998\/ark.5550190.0008.402<\/a>.<\/li>\n<li>[11] F. Y. Edamura, A. Nickon, J. Org. Chem. 1970, 35, 1509. doi: <a href=\"https:\/\/doi.org\/10.1021\/jo00830a055\">10.1021\/jo00830a055<\/a>.<\/li>\n<li>[12] Y. D. Boyko, C. J. Huck, D. Sarlah, J. Am. Chem. Soc. 2019, 141, 14131. doi: <a href=\"https:\/\/doi.org\/10.1021\/jacs.9b08487\">10.1021\/jacs.9b08487<\/a>.<\/li>\n<\/ul>\n<h4><strong>\u53cd\u5e94\u673a\u7406<\/strong><\/h4>\n<p><span style=\"color: #0000ff;\"><strong>\u787c\u70f7\u53c2\u4e0e\u7684<\/strong><strong>Caglioti<\/strong><strong>\u53cd\u5e94<\/strong><\/span><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/4-1.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31889 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/4-1.jpg\" alt=\"\" width=\"720\" height=\"568\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/4-1.jpg 1252w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/4-1-300x237.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/4-1-680x536.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/4-1-768x605.jpg 768w\" sizes=\"(max-width: 720px) 100vw, 720px\" \/><\/a><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/5.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31890 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/5.jpg\" alt=\"\" width=\"695\" height=\"303\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/5.jpg 1237w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/5-300x131.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/5-680x296.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/5-768x335.jpg 768w\" sizes=\"(max-width: 695px) 100vw, 695px\" \/><\/a><\/p>\n<p><span style=\"color: #0000ff;\"><strong>LiAlH<sub>4<\/sub><\/strong><strong>\u53c2<\/strong><strong>\u4e0e\u7684<\/strong><strong>Caglioti<\/strong><strong>\u53cd\u5e94<\/strong><\/span><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/6.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31891 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/6.jpg\" alt=\"\" width=\"725\" height=\"156\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/6.jpg 1234w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/6-300x64.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/6-680x146.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/6-768x165.jpg 768w\" sizes=\"(max-width: 725px) 100vw, 725px\" \/><\/a><\/p>\n<p><span style=\"color: #0000ff;\"><strong>NaBH<sub>3<\/sub>CN<\/strong><strong>\u53c2\u4e0e\u7684<\/strong><strong>Caglioti<\/strong><strong>\u53cd\u5e94<\/strong><\/span><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/7.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31892 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/7.jpg\" alt=\"\" width=\"740\" height=\"521\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/7.jpg 1226w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/7-300x211.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/7-680x479.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/7-768x541.jpg 768w\" sizes=\"(max-width: 740px) 100vw, 740px\" \/><\/a><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/8.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31893 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/8.jpg\" alt=\"\" width=\"734\" height=\"121\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/8.jpg 1274w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/8-300x49.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/8-680x112.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/8-768x127.jpg 768w\" sizes=\"(max-width: 734px) 100vw, 734px\" \/><\/a><\/p>\n<p><span style=\"color: #0000ff;\"><strong>\u513f\u8336\u915a\u787c\u70f7\u53c2\u4e0e\u7684<\/strong><strong>Caglioti<\/strong><strong>\u53cd\u5e94<\/strong><\/span><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/9.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31894 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/9.jpg\" alt=\"\" width=\"676\" height=\"303\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/9.jpg 1168w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/9-300x135.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/9-680x305.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/9-768x345.jpg 768w\" sizes=\"(max-width: 676px) 100vw, 676px\" \/><\/a><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/10.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31895 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/10.jpg\" alt=\"\" width=\"748\" height=\"351\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/10.jpg 1169w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/10-300x141.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/10-680x319.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/10-768x361.jpg 768w\" sizes=\"(max-width: 748px) 100vw, 748px\" \/><\/a><\/p>\n<h4><strong>\u53c2\u8003\u6587\u732e<\/strong><\/h4>\n<ul>\n<li>[1] C. F. Lane, Chem. Rev. 1976, 76, 773. doi: <a href=\"https:\/\/doi.org\/10.1021\/cr60304a005\">10.1021\/cr60304a005<\/a>.<\/li>\n<li>[2] L. Caglioti, Tetrahedron 1966, 22, 487. doi: <a href=\"https:\/\/doi.org\/10.1016\/0040-4020(66)80015-7\">10.1016\/0040-4020(66)80015-7<\/a>.<\/li>\n<li>[3] G. W. Kabalka, J. D. Baker Jr, J. Org. Chem. 1975, 40, 1834. doi: <a href=\"https:\/\/doi.org\/10.1021\/jo00900a033\">10.1021\/jo00900a033<\/a>.<\/li>\n<li>[4] E. J. Taylor, C. Djerassi, J. Am. Chem. Soc. 1976, 98, 2275. doi: <a href=\"https:\/\/doi.org\/10.1021\/ja00424a046\">10.1021\/ja00424a046<\/a>.<\/li>\n<\/ul>\n<h4><strong>\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/h4>\n<p>cyclopentane phosphine oxides\u7684\u5408\u6210<sup>[1]<\/sup><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/11.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31896 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/11.jpg\" alt=\"\" width=\"744\" height=\"139\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/11.jpg 1158w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/11-300x56.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/11-680x127.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/11-768x143.jpg 768w\" sizes=\"(max-width: 744px) 100vw, 744px\" \/><\/a><\/p>\n<p>(Z)-9-tricosene\u7684\u5408\u6210<sup>[2]<\/sup><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/12.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31897 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/12.jpg\" alt=\"\" width=\"710\" height=\"135\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/12.jpg 941w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/12-300x57.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/12-680x129.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/12-768x146.jpg 768w\" sizes=\"(max-width: 710px) 100vw, 710px\" \/><\/a><\/p>\n<p>(\u00b1)-stelletin E\u7684\u5168\u5408\u6210<sup>[3]<\/sup><\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/13.jpg\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-31898 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/13.jpg\" alt=\"\" width=\"709\" height=\"278\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/13.jpg 1102w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/13-300x117.jpg 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/13-680x266.jpg 680w, https:\/\/assets.www.gsbet888.com\/uploads\/2020\/05\/13-768x300.jpg 768w\" sizes=\"(max-width: 709px) 100vw, 709px\" \/><\/a><\/p>\n<h4><strong>\u5b9e\u9a8c\u6b65\u9aa4<\/strong><\/h4>\n<p><span style=\"color: #0000ff;\"><strong>\u787c\u70f7\u53c2\u4e0e\u7684<\/strong><strong>Caglioti<\/strong><strong>\u53cd\u5e94<\/strong><\/span><\/p>\n<p>\u5c06\u5bf9\u7532\u82ef\u78fa\u9170\u8159\u5e95\u7269 (1eq.)\u4e0e\u787c\u6c22\u5316\u94a0 (16.7 eq.)\u653e\u5165\u8fde\u63a5\u6709\u6052\u538b\u6ef4\u6db2\u6f0f\u6597\u53ca\u51b7\u51dd\u7ba1\u7684\u4e09\u53e3\u70e7\u74f6\u4e2d\uff0c\u901a\u8fc7\u53cc\u6392\u7ba1\u62bd\u771f\u7a7a-\u6c2e\u6c14\u7f6e\u6362\u4e09\u6b21\u3002\u518d\u52a0\u5165\u8131\u6c14\u7684\u4e8c\u4e59\u4e8c\u9187\u4e8c\u7532\u919a (\u5e95\u7269\u6d53\u5ea6\u4e3a0.07 M)\u6eb6\u89e3\u3002\u901a\u8fc7cannula\u5411\u6052\u538b\u6ef4\u6db2\u6f0f\u6597\u5185\u52a0\u5165\u4e09\u6c1f\u5316\u787c-\u4e59\u919a\u914d\u5408\u7269\u3002\u4e4b\u540e\uff0c\u5f00\u542f\u6052\u538b\u6ef4\u6db2\u6f0f\u6597\u4e0b\u7aef\u6d3b\u585e\uff0c\u5c06\u4e09\u6c1f\u5316\u787c-\u4e59\u919a\u914d\u5408\u7269\u7f13\u6162\u6ef4\u52a0\u81f3\u4e0a\u8ff0\u6df7\u5408\u7269\u4e2d\u3002\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u6405\u62cc\u8fc7\u591c\u3002\u518d\u901a\u8fc7\u6052\u538b\u6ef4\u6db2\u6f0f\u6597\u52a0\u5165\u4e59\u9178\u9150 (90.6 eq.)\uff0c\u52a0\u70ed\u56de\u6d41\uff0c\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u53cd\u5e94\u6db2\u5012\u5165\u51b0\u6c34\u4e2d\uff0c\u518d\u52a0\u5165\u4e59\u919a\u8fdb\u884c\u8403\u53d6\u3002\u5c06\u5408\u5e76\u7684\u6709\u673a\u76f8\u4f9d\u6b21\u52a0\u516510%\u6c22\u6c27\u5316\u94a0\u6eb6\u6db2\u53ca\u6c34\u8fdb\u884c\u6d17\u6da4\uff0c\u968f\u540e\uff0c\u52a0\u5165\u65e0\u6c34\u786b\u9178\u94a0\u8fdb\u884c\u5e72\u71e5\u3002\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u5c06\u6b8b\u4f59\u56fa\u4f53\u901a\u8fc7\u7532\u9187\u91cd\u7ed3\u6676\u8fdb\u884c\u7eaf\u5316\uff0c\u83b7\u5f97\u6700\u7ec8\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n<p><span style=\"color: #0000ff;\"><strong>NaBH<sub>3<\/sub>CN<\/strong><strong>\u53c2\u4e0e\u7684<\/strong><strong>Caglioti<\/strong><strong>\u53cd\u5e94<\/strong><\/span><\/p>\n<p>\u5c06\u5bf9\u7532\u82ef\u78fa\u9170\u8159\u5e95\u7269 (1eq.)\u52a0\u5165\u542b\u6709\u5c11\u91cf\u5bf9\u7532\u82ef\u78fa\u9178 (0.15eq.)\u7684DMF\u4e0e\u73af\u4e01\u781c\u6df7\u5408\u6eb6\u5242 (\u5e95\u7269\u6d53\u5ea6\u4e3a0.2 M)\u6eb6\u89e3\uff0c\u518d\u52a0\u5165\u6c30\u57fa\u787c\u6c22\u5316\u94a0 (4 eq.)\u53ca\u9002\u91cf\u73af\u5df1\u70f7\u3002\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u5728100-105 <sup>o<\/sup>C\u4e0b\u52a0\u70ed\uff0c\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u53cd\u5e94\u6db2\u52a0\u5165\u9002\u91cf\u6c34\u8fdb\u884c\u7a00\u91ca\uff0c\u518d\u52a0\u5165\u73af\u5df1\u70f7\u8fdb\u884c\u8403\u53d6\u3002\u5c06\u5408\u5e76\u7684\u6709\u673a\u76f8\u52a0\u5165\u6c34\u8fdb\u884c\u6d17\u6da4\uff0c\u968f\u540e\uff0c\u52a0\u5165\u65e0\u6c34\u786b\u9178\u94a0\u8fdb\u884c\u5e72\u71e5\u3002\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u5c06\u6b8b\u4f59\u7269\u5728\u771f\u7a7a\u6761\u4ef6\u4e0b\u8fdb\u884c\u84b8\u998f\u7eaf\u5316\uff0c\u83b7\u5f97\u6700\u7ec8\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n<p><span style=\"color: #0000ff;\"><strong>LiAlH<sub>4<\/sub><\/strong><strong>\u53c2<\/strong><strong>\u4e0e\u7684<\/strong><strong>Caglioti<\/strong><strong>\u53cd\u5e94<\/strong><\/span><\/p>\n<p>\u57280 <sup>o<\/sup>C\uff0c\u6c2e\u6c14\u6c14\u6c1b\u4e0b\uff0c\u5411\u5bf9\u7532\u82ef\u78fa\u9170\u8159\u5e95\u7269 (1eq.) \u7684\u65e0\u6c34\u56db\u6c22\u544b\u5583\u6eb6\u6db2 (\u5e95\u7269\u6d53\u5ea6\u4e3a0.13 M)\u4e2d\u7f13\u6162\u6ef4\u52a0\u6c22\u5316\u94dd\u9502 (3eq.)\u7684\u65e0\u6c34\u56db\u6c22\u544b\u5583\u6eb6\u6db2 (\u6c22\u5316\u94dd\u9502\u6d53\u5ea6\u4e3a0.26 M)\u3002\u6ef4\u52a0\u5b8c\u6210\u540e\uff0c\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u572860<sup>o<\/sup>C\u4e0b\u52a0\u70ed\uff0c\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u53cd\u5e94\u6db2\u51b7\u5374\u81f3\u5ba4\u6e29\uff0c\u4f9d\u6b21\u52a0\u5165\u9002\u91cf\u51b7\u6c34\u8fdb\u884c\u7a00\u91ca\uff0c\u518d\u52a0\u51652 M \u76d0\u9178\u9178\u5316\u540e\uff0c\u52a0\u5165\u6b63\u620a\u70f7\u8fdb\u884c\u8403\u53d6\u3002\u5c06\u5408\u5e76\u7684\u6709\u673a\u76f8\u91c7\u7528\u65e0\u6c34\u786b\u9178\u94a0\u8fdb\u884c\u5e72\u71e5\u3002\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u518d\u5c06\u6b8b\u4f59\u7269\u901a\u8fc7\u77ed\u7845\u80f6\u67f1\u7eaf\u5316 (\u6b63\u620a\u70f7\/\u620a\u82ef\u4f5c\u4e3a\u6d17\u8131\u5242)\uff0c\u83b7\u5f97\u6700\u7ec8\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n<p><span style=\"color: #0000ff;\"><strong>\u513f\u8336\u915a\u787c\u70f7\u53c2\u4e0e\u7684<\/strong><strong>Caglioti<\/strong><strong>\u53cd\u5e94<\/strong><\/span><\/p>\n<p>\u57280 <sup>o<\/sup>C\uff0c\u6c2e\u6c14\u6c14\u6c1b\u4e0b\uff0c\u7528\u6ce8\u5c04\u5668\u5411\u5bf9\u7532\u82ef\u78fa\u9170\u8159\u5e95\u7269 (1eq.) \u7684\u4e09\u6c2f\u7532\u70f7\u6eb6\u6db2 (\u5e95\u7269\u6d53\u5ea6\u4e3a0.42 M)\u4e2d\u52a0\u5165\u513f\u8336\u915a\u787c\u70f7 (1.1 eq.)\uff0c\u518d\u52a0\u5165\u4e59\u9178\u94a0\u6216\u4e59\u9178\u94ef (3eq.)\u3002\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u8fdb\u884c\u52a0\u70ed\u56de\u6d41\uff0c\u76f4\u81f3\u53cd\u5e94\u7ed3\u675f\u3002\u53cd\u5e94\u7ed3\u675f\u540e\uff0c\u5c06\u53cd\u5e94\u6db2\u51b7\u5374\u81f3\u5ba4\u6e29\uff0c\u9996\u5148\uff0c\u52a0\u5165\u9002\u91cf\u51b7\u6c34\u8fdb\u884c\u7a00\u91ca\uff0c\u518d\u52a0\u5165\u4e09\u6c2f\u7532\u70f7\u8fdb\u884c\u8403\u53d6\u3002\u5c06\u5408\u5e76\u7684\u6709\u673a\u76f8\u91c7\u7528\u65e0\u6c34\u786b\u9178\u94a0\u5e72\u71e5\u3002\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u5c06\u6b8b\u4f59\u7269\u901a\u8fc7\u7845\u80f6\u67f1\u8272\u8c31\u7eaf\u5316\uff0c\u83b7\u5f97\u6700\u7ec8\u76ee\u6807\u4ea7\u7269\u3002<\/p>\n<h4><strong>\u53c2\u8003\u6587\u732e<\/strong><\/h4>\n<ul>\n<li>[1] P. Camps, G. Colet, S. Segura, S. V\u00e1zquez, ARKIVOC 2007, (iv) 8. doi: <a href=\"https:\/\/doi.org\/10.3998\/ark.5550190.0008.402\">10.3998\/ark.5550190.0008.402<\/a>.<\/li>\n<li>[2] R. Ballini, M. Petrini, G. Rosini, J. Org. Chem. 1990, 55, 5159. doi: <a href=\"https:\/\/doi.org\/10.1021\/jo00304a032\">10.1021\/jo00304a032<\/a>.<\/li>\n<li>[3] Y. D. Boyko, C. J. Huck, D. Sarlah, J. Am. Chem. Soc. 2019, 141, 14131. doi: <a href=\"https:\/\/doi.org\/10.1021\/jacs.9b08487\">10.1021\/jacs.9b08487<\/a>.<\/li>\n<\/ul>\n<p>\u672c\u6587\u7248\u6743\u5c5e\u4e8e<strong>\u00a0<a href=\"\/\/www.gsbet888.com\/\">Chem-Station\u5316\u5b66\u7a7a\u95f4<\/a>\uff0c<\/strong>\u00a0\u6b22\u8fce\u70b9\u51fb\u6309\u94ae\u5206\u4eab\uff0c\u672a\u7ecf\u8bb8\u53ef\uff0c\u8c22\u7edd\u8f6c\u8f7d\uff01<\/p>\n","protected":false},"excerpt":{"rendered":"\u6982\u8981 Caglioti\u53cd\u5e94 (Caglioti reaction)\u662f\u5c06\u919b\u3001\u916e\u6216\u4e0e\u5176\u76f8\u5bf9\u5e94\u7684\u5bf9\u7532\u82ef\u78fa\u9170\u8159\u5728\u6c22\u5316\u7269 (\u5982NaBH4, LiAlH4, NaBH3CN, B2H6\u7b49)\u4f5c\u7528\u4e0b\uff0c\u751f\u6210\u70f7\u70c3\u6216\u70ef\u70c3 (\u5bf9\u4e8e\u03b1, \u03b2-\u4e0d\u9971\u548c\u919b\u53ca\u916e)\u7684\u53cd\u5e94\uff0c\u53c8\u79f0\u4e3aCaglioti\u8fd8\u539f (Caglioti reduction)\u6216Caglioti\u70ef\u70c3\u5408\u6210 (Caglioti alkene synthesis) [1]-[6]\u3002 \u8be5\u53cd\u5e94\u7531\u610f\u5927\u5229\u901a\u7528\u5316\u5b66\u7814\u7a76\u6240 (Istituto di Chimica Generale)\u7684L. Caglioti\u57281962\u5e74\u9996\u6b21\u62a5\u9053[1]\u3002\u8be5\u65b9\u6cd5\u4e2d\uff0c\u76ee\u6807\u4ea7\u7269\u70f7\u70c3 (\u53ef\u4f5c\u4e3aWolff-Kishner\u8fd8\u539f, Wolff-Kishner\u8fd8\u539fHuang-Minlon\u6539\u8fdb\u6cd5\u53caClemmensen\u8fd8\u539f\u7684\u6709\u6548\u66ff\u4ee3\u65b9\u6cd5)\u6216\u70ef\u70c3\u4ea7\u7269\u4ea7\u7387\u826f\u597d\u3002\u7136\u800c\uff0c\u53cd\u5e94\u6761\u4ef6\u8f83\u4e3a\u82db\u523b\uff0c\u4f8b\u5982\uff0c\u5728\u91c7\u7528\u787c\u70f7\/\u4e59\u9178\u9150\u4f53\u7cfb\u65f6\uff0c\u53cd\u5e94\u76f8\u4f9d\u5341\u5206\u4e25\u683c\u7684\u65e0\u6c34\u65e0\u6c27\u6761\u4ef6\uff0c\u800c\u4e14\uff0c\u8fd8\u539f\u5242\u7528\u91cf\u8f83\u5927\uff0c\u5728\u53cd\u5e94\u8fc7\u7a0b\u4e2d\u4f1a\u4f7f\u90e8\u5206\u5e95\u7269\u51fa\u73b0\u8f83\u591a\u7684\u526f\u53cd\u5e94[3]\u3002\u53e6\u5916\uff0c\u91c7\u7528\u6c22\u5316\u94dd\u9502\u65f6\uff0c\u53cd\u5e94\u8fc7\u7a0b\u4e2d\uff0c\u5316\u5b66\u9009\u62e9\u6027\u53ca\u5b98\u80fd\u56e2\u517c\u5bb9\u6027\u53ef\u80fd\u8f83\u5dee\uff0c\u5e95\u7269\u9002\u7528\u8303\u56f4\u8f83\u4e3a\u6709\u9650[7]\u3002 \u4e3a\u89e3\u51b3\u8fd9\u4e9b\u95ee\u9898\uff0c1975\u5e74Kabalka\u8bfe\u9898\u7ec4\u7814\u7a76\u53d1\u73b0\uff0c\u91c7\u7528\u513f\u8336\u915a\u787c\u70f7 (catecholborane)\uff0c\u80fd\u591f\u4f7f\u53cd\u5e94\u6761\u4ef6\u66f4\u52a0\u6e29\u548c\uff0c\u8bd5\u5242\u7528\u91cf\u53ca\u526f\u53cd\u5e94\u5927\u4e3a\u51cf\u5c11\u3002\u540c\u65f6\uff0c\u5177\u6709\u66f4\u52a0\u4f18\u826f\u7684\u4ea7\u7387\u53ca\u5b98\u80fd\u56e2\u517c\u5bb9\u6027[8]-[9]\u3002\u6587\u732e\u4e2d\u5c06\u8fd9\u79cd\u6539\u8fdb\u7684Caglioti\u53cd\u5e94\u79f0\u4e3aKabalka\u6539\u8fdb\u6cd5 (Kabalka modification)\u3002 \u76ee\u524d\uff0c\u8be5\u53cd\u5e94\u5df2\u6210\u4e3a\u6709\u673a\u5408\u6210\u8fc7\u7a0b\u4e2d\u5f15\u5165\u70f7\u70c3\u6216\u70ef\u70c3\u5355\u5143\u7684\u6709\u6548\u65b9\u6cd5\uff0c\u5728\u590d\u6742\u6709\u673a\u5206\u5b50\u5408\u6210\u8bbe\u8ba1\u53ca\u5929\u7136\u4ea7\u7269\u5168\u5408\u6210\u8fc7\u7a0b\u4e2d\u6709\u6f5c\u5728\u7684\u5e94\u7528\u4ef7\u503c[10]-[12]\u3002 \u57fa\u672c\u6587\u732e [1] L. Caglioti, M. Magi, Tetrahedron Lett. 1962, 18, 1261. doi: 10.1016\/S0040-4039(00)62045-2.. [2] L. Caglioti, M. Magi, Tetrahedron 1963, 19, 1127. doi: 10.1016\/S0040-4020(01)98571-0. [3] R. C. Cambie, P. S. Rutledge, D. W. Scott, P. D. Woodgate, Aust. J. Chem. 1979, 32, 695. doi: 10.1071\/CH9790695. [4] R. O. Hutchins, C. A. Milewski, B. E. Maryanoff, J. Am. Chem. Soc. 1973, 95, 3662. doi: 10.1021\/ja00792a033. [5] R. O. Hutchins, B. E. Maryanoff, C. A. Milewski, J. Am. Chem. Soc. 1971, 93, 1793. 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