{"id":802,"date":"2014-03-21T11:27:15","date_gmt":"2014-03-21T03:27:15","guid":{"rendered":"\/\/www.gsbet888.com\/?p=802"},"modified":"2019-08-02T18:57:10","modified_gmt":"2019-08-02T10:57:10","slug":"%e6%b2%83%e5%b0%94%e5%a4%ab%ef%bc%8d%e5%87%af%e6%83%9c%e7%ba%b3%e8%bf%98%e5%8e%9fwolff-kishner-reduction","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2014\/03\/%e6%b2%83%e5%b0%94%e5%a4%ab%ef%bc%8d%e5%87%af%e6%83%9c%e7%ba%b3%e8%bf%98%e5%8e%9fwolff-kishner-reduction.html","title":{"rendered":"\u6c83\u5c14\u592b\uff0d\u51ef\u60dc\u7eb3\u8fd8\u539f(Wolff-Kishner Reduction)"},"content":{"rendered":"

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\u5728NaOH\u6216\u8005KOH\u5b58\u5728\u4e0b\uff0c\u919b\u6216\u916e\u4e0e\u80bc\u5728\u4e59\u4e8c\u9187\u4e2d\u52a0\u70ed\uff0c\u5f62\u6210\u78b3\u6c22\u5316\u5408\u7269(\u9ec4\u9e23\u9f99\u6cd5)\u3002Clemmensen\u8fd8\u539f\u662f\u5728\u9178\u6027\u6761\u4ef6\u4e0b\u8fdb\u884c\u7684\uff0c\u800c\u672c\u53cd\u5e94\u4f5c\u4e3a\u5176\u76f8\u8f85\u52a9\u7684\u53cd\u5e94\u53ef\u4ee5\u5728\u78b1\u6027\u6761\u4ef6\u4e0b\u8fdb\u884c\u3002<\/p>\n
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\u57fa\u672c\u6587\u732e<\/strong><\/li>\n<\/ul>\n
\u30fbKishner, N. J. Russ. Phys. Chem. Soc.<\/em> 1911<\/strong>,\u00a043<\/em>, 582.
\n\u30fbWolff, L. Ann.<\/em> 1912<\/strong>, 394<\/em>, 86.
\n\u30fbHuang-Minlon Modification: (a) Minlon, H. J. Am. Chem. Soc.<\/em>\u00a01946<\/strong>, 68<\/em>, 2487. DOI: 10.1021\/ja01216a013<\/a>\u00a0(b) idem. J. Am. Chem. Soc.<\/em> 1949<\/strong>, 71<\/em>,\u00a03301. DOI: 10.1021\/ja01178a008<\/a>\u00a0(c) Hunig, S.; Lucke, E.; Brenningesr, W. Org. Synth.<\/em> 1963<\/strong>,\u00a0\u00a043<\/em>, 34.
\n\u30fbTodd, D. Org. React.<\/em> 1948<\/strong>, 4<\/em>,\u00a0378.
\n\u30fbSzmant, H. H. Angew. Chem., Int. Ed. Engl.<\/em> 1968<\/strong>,\u00a07<\/em>, 120.
\n\u30fbHutchins, R. O.; Hutchins, M. K. Comprehensive Organic Synthesis<\/em>\u00a01991<\/strong>, 8<\/em>, 327.<\/p>\n
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\u53cd\u5e94\u673a\u7406<\/strong><\/li>\n<\/ul>\n
\u78b3\u4f4d\u83b7\u5f97\u8d28\u5b50\u7684\u8fc7\u7a0b\u662f\u8be5\u53cd\u5e94\u7684\u9650\u901f\u6b65\u9aa4\u3002 $\"al-ane2.gif\"$ <\/p>\n
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\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/li>\n<\/ul>\n
\u5178\u578b\u7684\u5316\u5b66\u9009\u62e9\u6027\u7684\u4f8b\u5b50 $\"al-ane3.gif\"$ \u5982\u679c\u4f7f\u7528\u5bf9\u7532\u57fa\u82ef\u78fa\u9170\u80bc\u548c\u6c30\u57fa\u787c\u6c22\u5316\u94a0\u7684\u6761\u4ef6\u7684\u8bdd\u3001\u53ef\u4ee5\u4e00\u4e0b\u5b50\u4ece\u916e\u5f97\u5230\u70f7\u70c3[1]\u3002 $\"wolff_kishner_4.gif\"$ \u916e\u4e0e\u80bc\u53cd\u5e94\u751f\u6210\u7684\u8159\u5728DMSO-^{t<\/sup>BuOH\u7684\u6df7\u5408\u6eb6\u5242\u4e2d\u3001\u4e0e\u53d4\u4e01\u9187\u94be\u53cd\u5e94\u7684\u8bdd\uff0cWolff-Kishner\u8fd8\u539f\u53cd\u5e94\u5728\u5ba4\u6e29\u6761\u4ef6\u4e0b\u5c31\u80fd\u8fdb\u884c\u3002\u53ccTBS\u53d6\u4ee3\u7684\u80bc\u4e0e\u916e\u53cd\u5e94\u7684\u8bdd\u3001\u53ef\u4ee5\u66f4\u52a0\u9ad8\u6548\u7684\u751f\u6210\u8159(Cram-Myers\u6539\u826f\u6cd5<\/strong>)[2] \u00a0Neotripterifordin\u306e\u5408\u6210[3]\n}
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\u53c2\u8003\u6587\u732e<\/strong><\/li>\n<\/ul>\n[1] Hutchins, R. O.; Milewski, C. A.; Maryanoff, B. E. J. Am.\u00a0Chem. Soc.<\/em> 1973<\/strong>, 95<\/em>, 3662. DOI: 10.1021\/ja00792a03<\/a>
\n[2] Furrow, M. E.; Myers, A. G. J. Am. Chem. Soc.<\/em> 2004<\/strong>,\u00a0126<\/em>, 5436. DOI: 10.1021\/ja049694s <\/a>
\n[3] Corey, E. J.; Liu, K. J. Am. Chem. Soc.<\/em> 1997<\/strong>,\u00a0119<\/em>, 9929. DOI: 10.1021\/ja972549c<\/a><\/p>\n
<\/p>\n","protected":false},"excerpt":{"rendered":"\u919b\u3001\u916e\u2192\u70f7\u70c3 \u6982\u8981 \u7fb0\u57fa\u8fd8\u539f\u6210\u4e9a\u7532\u57fa\u7684\u53cd\u5e94\u3002 \u5728NaOH\u6216\u8005KOH\u5b58\u5728\u4e0b\uff0c\u919b\u6216\u916e\u4e0e\u80bc\u5728\u4e59\u4e8c\u9187\u4e2d\u52a0\u70ed\uff0c\u5f62\u6210\u78b3\u6c22\u5316\u5408\u7269(\u9ec4\u9e23\u9f99\u6cd5)\u3002Clemmensen\u8fd8\u539f\u662f\u5728\u9178\u6027\u6761\u4ef6\u4e0b\u8fdb\u884c\u7684\uff0c\u800c\u672c\u53cd\u5e94\u4f5c\u4e3a\u5176\u76f8\u8f85\u52a9\u7684\u53cd\u5e94\u53ef\u4ee5\u5728\u78b1\u6027\u6761\u4ef6\u4e0b\u8fdb\u884c\u3002 \u8159\u53ef\u4ee5\u88ab\u7f29\u6c28\u57fa\u8132\u6216\u8005\u5076\u6c2e\u5316\u5408\u7269\u66ff\u4ee3\u4f5c\u4e3a\u524d\u5bfc\u5316\u5408\u7269(precursor)\u4f7f\u7528\uff0c\u540c\u6837\u7684\u53ef\u4ee5\u8fdb\u884c\u8be5\u8fd8\u539f\u53cd\u5e94\u3002 \u57fa\u672c\u6587\u732e \u30fbKishner, N. J. Russ. Phys. Chem. Soc. 1911,\u00a043, 582. \u30fbWolff, L. Ann. 1912, 394, 86. \u30fbHuang-Minlon Modification: (a) Minlon, H. J. Am. Chem. Soc.\u00a01946, 68, 2487. DOI: 10.1021\/ja01216a013\u00a0(b) idem. J. Am. Chem. Soc. 1949, 71,\u00a03301. DOI: 10.1021\/ja01178a008\u00a0(c) Hunig, S.; Lucke, E.; Brenningesr, W. Org. Synth. 1963,\u00a0\u00a043, 34. \u30fbTodd, D. Org. React. 1948, 4,\u00a0378. \u30fbSzmant, H. H. Angew. Chem., Int. Ed. Engl. 1968,\u00a07, 120. \u30fbHutchins, R. O.; Hutchins, M. K. Comprehensive Organic Synthesis\u00a01991, 8, 327. \u53cd\u5e94\u673a\u7406 \u78b3\u4f4d\u83b7\u5f97\u8d28\u5b50\u7684\u8fc7\u7a0b\u662f\u8be5\u53cd\u5e94\u7684\u9650\u901f\u6b65\u9aa4\u3002 \u53cd\u5e94\u5b9e\u4f8b \u5178\u578b\u7684\u5316\u5b66\u9009\u62e9\u6027\u7684\u4f8b\u5b50\u5982\u679c\u4f7f\u7528\u5bf9\u7532\u57fa\u82ef\u78fa\u9170\u80bc\u548c\u6c30\u57fa\u787c\u6c22\u5316\u94a0\u7684\u6761\u4ef6\u7684\u8bdd\u3001\u53ef\u4ee5\u4e00\u4e0b\u5b50\u4ece\u916e\u5f97\u5230\u70f7\u70c3[1]\u3002 \u916e\u4e0e\u80bc\u53cd\u5e94\u751f\u6210\u7684\u8159\u5728DMSO-tBuOH\u7684\u6df7\u5408\u6eb6\u5242\u4e2d\u3001\u4e0e\u53d4\u4e01\u9187\u94be\u53cd\u5e94\u7684\u8bdd\uff0cWolff-Kishner\u8fd8\u539f\u53cd\u5e94\u5728\u5ba4\u6e29\u6761\u4ef6\u4e0b\u5c31\u80fd\u8fdb\u884c\u3002\u53ccTBS\u53d6\u4ee3\u7684\u80bc\u4e0e\u916e\u53cd\u5e94\u7684\u8bdd\u3001\u53ef\u4ee5\u66f4\u52a0\u9ad8\u6548\u7684\u751f\u6210\u8159(Cram-Myers\u6539\u826f\u6cd5)[2] \u00a0Neotripterifordin\u306e\u5408\u6210[3] \u5b9e\u9a8c\u6b65\u9aa4 \u5b9e\u9a8c\u6280\u5de7 \u53c2\u8003\u6587\u732e [1] Hutchins, R. O.; Milewski, C. A.; Maryanoff, B. E. J. Am.\u00a0Chem. Soc. 1973, 95, […]","protected":false},"author":5,"featured_media":804,"comment_status":"closed","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","enabled":false},"version":2}},"categories":[2],"tags":[454,476,477],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/03\/al-ane1.gif","jetpack_shortlink":"https:\/\/wp.me\/p96op1-cW","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/802"}],"collection":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/users\/5"}],"replies":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/comments?post=802"}],"version-history":[{"count":2,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/802\/revisions"}],"predecessor-version":[{"id":28269,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/802\/revisions\/28269"}],"wp:featuredmedia":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media\/804"}],"wp:attachment":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media?parent=802"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/categories?post=802"},{"taxonomy":"post_tag","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/tags?post=802"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}