{"id":24392,"date":"2019-02-07T09:32:13","date_gmt":"2019-02-07T01:32:13","guid":{"rendered":"\/\/www.gsbet888.com\/?p=24392"},"modified":"2019-02-07T09:32:13","modified_gmt":"2019-02-07T01:32:13","slug":"%e7%a1%ab%e9%85%b8%e9%85%af%e7%9a%84%e5%90%88%e6%88%90-synthesis-of-organosulfate","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2019\/02\/%e7%a1%ab%e9%85%b8%e9%85%af%e7%9a%84%e5%90%88%e6%88%90-synthesis-of-organosulfate.html","title":{"rendered":"\u786b\u9178\u916f\u7684\u5408\u6210 Synthesis of Organosulfate"},"content":{"rendered":"<h4>\u6982\u8981<\/h4>\n<p><strong>\u786b\u9178\u916f\uff08organosulfate\uff09<\/strong>\u662f\u5b58\u5728\u4e8e\u5f88\u591a\u751f\u7269\u6d3b\u6027\u5316\u5408\u7269\u4e2d\u7684\u5b98\u80fd\u56e2\u3002\u53e6\u5916\u6c34\u89e3\u80fd\u653e\u51fa\u9187\uff0c\u5b83\u8fd8\u7528\u5728\u524d\u836f\u4e0a\u4ee5\u589e\u5f3a\u6c34\u6eb6\u6027\u3002<br \/>\n\u4ee5\u5f80\u5e38\u5e38\u4f7f\u7528\u786b\u9178\uff0c\u6c28\u57fa\u78fa\u9178\u7b49\u4f5c\u4e3a\u786b\u9178\u5316\u5242\u7528\u4e8e\u786b\u9178\u916f\u7684\u5408\u6210\u3002\u7136\u800c\uff0c\u9700\u8981\u5728\u8131\u6c34\u6761\u4ef6\uff08Dean-Stark\u88c5\u7f6e\u548c\u7f29\u5408\u5242\uff09\u4e0b\u8fdb\u884c\uff0c\u5e76\u4e14\u7531\u4e8e\u5f3a\u9178\u6027\u7684\u7f18\u6545\uff0c\u5bb9\u6613\u53d1\u751f\u526f\u53cd\u5e94\u3002<br \/>\n\u53e6\u5916\u53cd\u5e94\u6d3b\u6027\u79cdSO<sub>3<\/sub>\u7531\u4e8e\u662f\u6c14\u4f53\uff0c\u53d6\u7528\uff0c\u5904\u7406\u90fd\u5f88\u9ebb\u70e6\u3002\u5728\u8fd9\u4e9b\u60c5\u51b5\u4e0b\uff0c\u901a\u5e38\u6539\u7528\u5728\u5ba4\u6e29\u4e0b\u4e3a\u56fa\u4f53\uff0c\u4e14\u5177\u6709\u9ad8\u7a33\u5b9a\u6027\u7684<strong>SO<sub>3<\/sub>\uff65\u8def\u6613\u65af\u78b1\u7edc\u5408\u7269<\/strong>\u8fdb\u884c\u786b\u9178\u5316\u7684\u65b9\u6cd5\u3002<br \/>\n\u5373\u4f7f\u5982\u6b64\uff0c\u8fd8\u5b58\u5728\u8bf8\u5982\u79bb\u5b50\u6027\u4ea7\u7269\u7684\u7eaf\u5316\u56f0\u96be\uff0c\u8131\u916f\u5316\u4e0e\u916f\u5316\u7684\u7ade\u4e89\uff0c\u65e0\u6cd5\u5728\u6e29\u548c\u6761\u4ef6\u4e0b\u8fdb\u884c\u7b49\u5c1a\u672a\u89e3\u51b3\u7684\u95ee\u9898\u3002<\/p>\n<h4>\u57fa\u672c\u6587\u732e<\/h4>\n<h5>&lt;Review&gt;<\/h5>\n<ul>\n<li>Al-Horani, R. A.; Desai, U. R. <em>Tetrahedron<\/em> <strong>2010<\/strong>, <em>66<\/em>, 2907. doi:<a href=\"https:\/\/doi.org\/10.1016\/j.tet.2010.02.015\">10.1016\/j.tet.2010.02.015<\/a><\/li>\n<li>Stone, M. J.; Payne, R. J. <em>Acc. Chem. Res.<\/em> <strong>2015<\/strong>, <em>48<\/em>, 2251. DOI: <a href=\"https:\/\/doi.org\/10.1021\/acs.accounts.5b00255\">10.1021\/acs.accounts.5b00255<\/a><\/li>\n<li>Vale, N.; Carvalho, R.; Gomes, V. R.<em> Eur. J. Org. Chem.<\/em> <strong>2015<\/strong>, <em>34<\/em>, 7413. doi:<a href=\"https:\/\/doi.org\/10.1002\/ejoc.201500715\">10.1002\/ejoc.201500715<\/a><\/li>\n<\/ul>\n<h4>\u53cd\u5e94\u673a\u7406<\/h4>\n<p><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-24394 \" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2019\/01\/sulfation_6.png\" alt=\"\" width=\"450\" height=\"167\" srcset=\"https:\/\/assets.www.gsbet888.com\/uploads\/2019\/01\/sulfation_6.png 768w, https:\/\/assets.www.gsbet888.com\/uploads\/2019\/01\/sulfation_6-300x111.png 300w, https:\/\/assets.www.gsbet888.com\/uploads\/2019\/01\/sulfation_6-680x252.png 680w\" sizes=\"(max-width: 450px) 100vw, 450px\" \/><\/p>\n<p>SO<sub>3<\/sub>\uff65\u8def\u6613\u65af\u78b1\u7edc\u5408\u7269\u662f\u968f\u7740\u4e0e\u8def\u6613\u65af\u78b1\u7684\u7ed3\u5408\u8d8a\u5f3a\uff0c\u53cd\u5e94\u6027\u8d8a\u5f31\uff0c\u5927\u81f4\u7684\u6d3b\u6027\u987a\u5e8f\u5982\u4e0b\u56fe\u6240\u793a\u3002<\/p>\n<p><img loading=\"lazy\" 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F.; Iida, T. <em>Steroids<\/em> <strong>2009<\/strong>, <em>74<\/em>, 766. doi:<a href=\"https:\/\/doi.org\/10.1016\/j.steroids.2009.04.007\">10.1016\/j.steroids.2009.04.007<\/a><\/li>\n<li>Raghuraman, A.; Riaz, M.; Hindle, M.; Desai, U. R. <em>Tetrahedron Lett.<\/em> <strong>2007<\/strong>, <em>48<\/em>, 6754. doi:<a href=\"https:\/\/doi.org\/10.1016\/j.tetlet.2007.07.100\">10.1016\/j.tetlet.2007.07.100<\/a><\/li>\n<li>Krylov, V. B.; Ustyuzhanina, N. E.; Grachev, A. A.; Nifantiev, N. E. Tetrahedron Lett. 2008, 49, 5877. doi:<a href=\"https:\/\/doi.org\/10.1016\/j.tetlet.2008.07.135\">10.1016\/j.tetlet.2008.07.135<\/a><\/li>\n<li>Penney, C. L.; Perlin, A. S. <em>Carbohydr. Res.<\/em> <strong>1981<\/strong>, <em>93<\/em>, 241. doi:<a href=\"https:\/\/doi.org\/10.1016\/S0008-6215(00)80853-8\">10.1016\/S0008-6215(00)80853-8<\/a><\/li>\n<li>Proud, A. D.; Prodger, J. C.; Flitsch, S. L. <em>Tetrahedron Lett.<\/em> <strong>1997<\/strong>, <em>38<\/em>, 7243. doi:<a href=\"https:\/\/doi.org\/10.1016\/S0040-4039(97)01681-X\">10.1016\/S0040-4039(97)01681-X<\/a><\/li>\n<li>(a) Liu, Y.; Lien, I.-F. F.; Ruttgaizer, S.; Dove, P.; Taylor, S. D. <em>Org. Lett.<\/em> <strong>2004<\/strong>,<em> 6<\/em>, 209. doi:<a href=\"https:\/\/doi.org\/10.1021\/ol036157o\">10.1021\/ol036157o<\/a> (b) Gunnarsson, T. G.; Riaz, M.; Adams, J.; Desai, U. R. <em>Bioorg. Med. Chem.<\/em> <strong>2005<\/strong>, <em>13<\/em>, 1783. doi:<a href=\"https:\/\/doi.org\/10.1016\/j.bmc.2004.11.060\">10.1016\/j.bmc.2004.11.060<\/a><\/li>\n<li>(a) Ingram, L. J.; Taylor, S. D.<em> Angew. Chem., Int. Ed.<\/em> <strong>2006<\/strong>, <em>45<\/em>, 3503. doi:<a href=\"https:\/\/doi.org\/10.1002\/anie.200600153\">10.1002\/anie.200600153<\/a> \u00a0(b) Ingram, L. J.; Desoky, A.; Ali, A. M.; Taylor, S. <em>J. Org. Chem.<\/em> <strong>2009<\/strong>, <em>74<\/em>, 6479. DOI: <a href=\"https:\/\/doi.org\/10.1021\/jo9014112\">10.1021\/jo9014112<\/a><\/li>\n<li>(a) Fujii, N.; Futaki, S.; Funakoshi, S.; Akaji, K.; Morimoto, H.; Doi, R.; Inoue, K.; Kogire, M.; Sumi, S.; Yun, M.; Tobe, T.; Aono, M.; Matsuda, M.; Narusawa, H.; Moriga, M.; Yajima, H. <em>Chem. Pharm. Bull.<\/em> <strong>1988<\/strong>, <em>36<\/em>, 3281. doi:<a href=\"https:\/\/doi.org\/10.1248\/cpb.36.3281\">10.1248\/cpb.36.3281<\/a> (b) Futaki, S.; Taike, T.; Yagami, T.; Ogawa, T.; Akita, T.; Kitagawa, K. <em>J. Chem. Soc., Perkin Trans. 1<\/em> <strong>1990<\/strong>, 1739. doi:<a href=\"https:\/\/doi.org\/10.1039\/P19900001739\">10.1039\/P19900001739<\/a> (c) \u00a0Young, T.; Kiessling, L. L. <em>Angew. Chem. Int. Ed.<\/em><strong>2002<\/strong>, <em>41<\/em>, 3449. <a href=\"https:\/\/doi.org\/10.1002\/1521-3773(20020916)41:18%3C3449::AID-ANIE3449%3E3.0.CO;2-U\">[abstract]<\/a> (d) Taleski, D.; \u00a0Butler, S. J.; Stone, M. J.; Payne, R. J. <em>Chem. Asian J.<\/em> <strong>2011<\/strong>, <em>6<\/em>, 1316. doi:<a href=\"https:\/\/doi.org\/10.1002\/asia.201100232\">10.1002\/asia.201100232<\/a><\/li>\n<li>Ali, A. M.; Taylor, S. D. <em>Angew. Chem., Int. Ed.<\/em> <strong>2009<\/strong>, <em>44<\/em>, 2024. doi: <a href=\"https:\/\/doi.org\/10.1002\/anie.200805642\">10.1002\/anie.200805642<\/a><\/li>\n<li>Simpson, L. S.; Widlanski, T. S. \u00a0<em>J. Am. Chem. Soc.<\/em> <strong>2006<\/strong>, <em>128<\/em>, 1605. DOI: <a href=\"https:\/\/doi.org\/10.1021\/ja056086j\">10.1021\/ja056086j<\/a><\/li>\n<li>Chen, W.; Dong, J.; Li, S.; Liu, Y.; Wang, Y.; Yoon, L.; Wu, P.; Sharpless, K. B.; Kelly, J. W. <em>Angew. Chem. Int. Ed.<\/em> <strong>2016<\/strong>, <em>55<\/em>, 1835. doi:<a href=\"https:\/\/doi.org\/10.1002\/anie.201509016\">10.1002\/anie.201509016<\/a><\/li>\n<li>Sisler, H. H.; Audrieth, L. F. <em>Inorg. Synth.<\/em> <strong>1946<\/strong>, <em>2<\/em>, 173.<\/li>\n<\/ol>\n<h4>\u5173\u8054\u53cd\u5e94<\/h4>\n<ul>\n<li><a href=\"\/\/www.gsbet888.com\/reactions\/%e6%b0%a7%e5%8c%96%e5%8f%8d%e5%ba%94\/2014\/04\/parikh-doering%e6%b0%a7%e5%8c%96%e5%8f%8d%e5%ba%94-parikh-doering-oxidation.html\">Parikh-Doering Oxidation<\/a><\/li>\n<\/ul>\n<h4>\u5916\u90e8\u94fe\u63a5<\/h4>\n<ul>\n<li><a href=\"https:\/\/en.wikipedia.org\/wiki\/Organosulfate\">Organosulfate \u2013 Wikipedia<\/a><\/li>\n<li><a href=\"https:\/\/en.wikipedia.org\/wiki\/Sulfur_trioxide\">Sulfur trioxide \u2013 Wikipedia<\/a><\/li>\n<\/ul>\n<p><strong>\u672c\u6587\u7248\u6743\u5c5e\u4e8e\u00a0<a href=\"\/\/www.gsbet888.com\/\">Chem-Station\u5316\u5b66\u7a7a\u95f4<\/a>\uff0c \u6b22\u8fce\u70b9\u51fb\u6309\u94ae\u5206\u4eab\uff0c\u672a\u7ecf\u8bb8\u53ef\uff0c\u8c22\u7edd\u8f6c\u8f7d\uff01<\/strong><\/p>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"\u6982\u8981 \u786b\u9178\u916f\uff08organosulfate\uff09\u662f\u5b58\u5728\u4e8e\u5f88\u591a\u751f\u7269\u6d3b\u6027\u5316\u5408\u7269\u4e2d\u7684\u5b98\u80fd\u56e2\u3002\u53e6\u5916\u6c34\u89e3\u80fd\u653e\u51fa\u9187\uff0c\u5b83\u8fd8\u7528\u5728\u524d\u836f\u4e0a\u4ee5\u589e\u5f3a\u6c34\u6eb6\u6027\u3002 \u4ee5\u5f80\u5e38\u5e38\u4f7f\u7528\u786b\u9178\uff0c\u6c28\u57fa\u78fa\u9178\u7b49\u4f5c\u4e3a\u786b\u9178\u5316\u5242\u7528\u4e8e\u786b\u9178\u916f\u7684\u5408\u6210\u3002\u7136\u800c\uff0c\u9700\u8981\u5728\u8131\u6c34\u6761\u4ef6\uff08Dean-Stark\u88c5\u7f6e\u548c\u7f29\u5408\u5242\uff09\u4e0b\u8fdb\u884c\uff0c\u5e76\u4e14\u7531\u4e8e\u5f3a\u9178\u6027\u7684\u7f18\u6545\uff0c\u5bb9\u6613\u53d1\u751f\u526f\u53cd\u5e94\u3002 \u53e6\u5916\u53cd\u5e94\u6d3b\u6027\u79cdSO3\u7531\u4e8e\u662f\u6c14\u4f53\uff0c\u53d6\u7528\uff0c\u5904\u7406\u90fd\u5f88\u9ebb\u70e6\u3002\u5728\u8fd9\u4e9b\u60c5\u51b5\u4e0b\uff0c\u901a\u5e38\u6539\u7528\u5728\u5ba4\u6e29\u4e0b\u4e3a\u56fa\u4f53\uff0c\u4e14\u5177\u6709\u9ad8\u7a33\u5b9a\u6027\u7684SO3\uff65\u8def\u6613\u65af\u78b1\u7edc\u5408\u7269\u8fdb\u884c\u786b\u9178\u5316\u7684\u65b9\u6cd5\u3002 \u5373\u4f7f\u5982\u6b64\uff0c\u8fd8\u5b58\u5728\u8bf8\u5982\u79bb\u5b50\u6027\u4ea7\u7269\u7684\u7eaf\u5316\u56f0\u96be\uff0c\u8131\u916f\u5316\u4e0e\u916f\u5316\u7684\u7ade\u4e89\uff0c\u65e0\u6cd5\u5728\u6e29\u548c\u6761\u4ef6\u4e0b\u8fdb\u884c\u7b49\u5c1a\u672a\u89e3\u51b3\u7684\u95ee\u9898\u3002 \u57fa\u672c\u6587\u732e &lt;Review&gt; Al-Horani, R. A.; Desai, U. R. Tetrahedron 2010, 66, 2907. doi:10.1016\/j.tet.2010.02.015 Stone, M. J.; Payne, R. J. Acc. Chem. Res. 2015, 48, 2251. DOI: 10.1021\/acs.accounts.5b00255 Vale, N.; Carvalho, R.; Gomes, V. R. Eur. J. Org. Chem. 2015, 34, 7413. doi:10.1002\/ejoc.201500715 \u53cd\u5e94\u673a\u7406 SO3\uff65\u8def\u6613\u65af\u78b1\u7edc\u5408\u7269\u662f\u968f\u7740\u4e0e\u8def\u6613\u65af\u78b1\u7684\u7ed3\u5408\u8d8a\u5f3a\uff0c\u53cd\u5e94\u6027\u8d8a\u5f31\uff0c\u5927\u81f4\u7684\u6d3b\u6027\u987a\u5e8f\u5982\u4e0b\u56fe\u6240\u793a\u3002 \u968f\u7740\u53cd\u5e94\u8fdb\u884c\u5f15\u8d77anionic overcrowding\u3001\u7ee7\u800c\u5728\u6709\u673a\u6eb6\u5242\u4e2d\u7684\u6eb6\u89e3\u5ea6\u4e5f\u968f\u4e4b\u964d\u4f4e\u3001\u56e0\u6b64\u901a\u5e38\u96be\u4ee5\u5bf9\u591a\u4e2a\u7f9f\u57fa\u8fdb\u884c\u786b\u9178\u5316\u3002\u53e6\u5916\uff0c\u5728\u6c34\u4e2d\u4e5f\u80fd\u8fdb\u884c\u7684\u786b\u9178\u916f\u5316\u53cd\u5e94\u8fd8\u662f\u4e00\u4e2a\u96be\u9898\u3002 \u53cd\u5e94\u5b9e\u4f8b \u4f7f\u7528SO3\u7b49\u4ef7\u4f53\u7684\u786b\u9178\u5316\u53cd\u5e94 \u56fa\u9187\u7684\u786b\u9178\u5316[1] \u5fae\u6ce2\u6761\u4ef6\u4e0b\u7684\u786b\u9178\u5316[2]\uff1a\u591a\u915a\u7684\u591a\u78fa\u5316\u662f\u7279\u522b\u56f0\u96be\u7684\uff0c\u4f46\u5982\u679c\u4f7f\u7528\u8be5\u65b9\u6cd5\uff0c\u5219\u53ef\u4ee5\u4ee5\u826f\u597d\u7684\u6536\u7387\u83b7\u5f97\u6240\u9700\u7684\u4ea7\u7269\u3002 \u9178\u50ac\u5316\u4e0b\u7684\u786b\u9178\u5316[3]\uff1a\u4e0e\u78b1\u6027\u6761\u4ef6\u4e0d\u540c\u7684\u662f\uff0c\u8be5\u53cd\u5e94\u53ef\u4ee5\u5728\u4f4e\u6e29\u4e0b\u8fdb\u884c\u3002\u5bf9SO3\u914d\u4f4d\u7684\u80fa\u8fdb\u884c\u8d28\u5b50\u5316\uff0c\u6e38\u79bb\u51faSO3\u662f\u672c\u53cd\u5e94\u7684\u5173\u952e\u3002 \u901a\u8fc7\u4fdd\u62a4\u4f53\u5408\u6210 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F.; Iida, T. Steroids 2009, 74, 766. doi:10.1016\/j.steroids.2009.04.007 Raghuraman, A.; Riaz, M.; Hindle, M.; Desai, U. R. 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