{"id":64413,"date":"2015-08-19T09:12:09","date_gmt":"2015-08-19T01:12:09","guid":{"rendered":"http:\/\/highscope.ch.ntu.edu.tw\/wordpress\/?p=64413"},"modified":"2021-10-06T16:10:47","modified_gmt":"2021-10-06T08:10:47","slug":"%e4%bc%af%e5%a5%87%e9%82%84%e5%8e%9f%e5%8f%8d%e6%87%89","status":"publish","type":"post","link":"http:\/\/localhost\/%e4%bc%af%e5%a5%87%e9%82%84%e5%8e%9f%e5%8f%8d%e6%87%89\/","title":{"rendered":"\u4f2f\u5947\u9084\u539f\u53cd\u61c9"},"content":{"rendered":"

\u4f2f\u5947\u9084\u539f\u53cd\u61c9 (Brich Reduction)<\/strong><\/span>
\n\u570b\u7acb\u81fa\u7063\u5e2b\u7bc4\u5927\u5b78\u5316\u5b78\u7cfb\u78a9\u58eb\u73ed \u937e\u9577\u5fd7<\/strong><\/span><\/p>\n

\"66413_p1\"<\/a>

\u5716\u4e00 Arthur John Birch\uff08\u4f86\u6e90\uff1a\u53c3\u8003\u8cc7\u65994\uff09<\/p><\/div>\n

Arthur John Birch 1915\u5e74\u51fa\u751f\u65bc\u6fb3\u6d32\u96ea\u68a8\uff0c\u7562\u696d\u65bc\u96ea\u68a8\u5927\u5b78\uff0c\u4e4b\u5f8c\u66fe\u5230\u904e\u725b\u6d25\u5927\u5b78\u3001\u528d\u6a4b\u5927\u5b78\u3001\u66fc\u5fb9\u65af\u7279\u5927\u5b78\u6df1\u9020\u30021,4<\/sup><\/p>\n

Birch\u662f\u4e8c\u5341\u4e16\u7d00\u5091\u51fa\u6709\u6a5f\u5316\u5b78\u5bb6\u4e4b\u4e00\uff0c\u5728\u6709\u6a5f\u91d1\u5c6c\u5316\u5b78\u53ca\u751f\u7269\u5316\u5b78\u5177\u6709\u4e00\u5b9a\u7684\u5f71\u97ff\u529b\uff0c\u4ed6\u975e\u51e1\u7684\u5275\u9020\u529b\u4f7f\u5f97\u4ed6\u5728\u79d1\u5b78\u4e0a\u4eab\u8b7d\u76db\u540d\u3002\u5176\u4e2d\u6700\u88ab\u4eba\u719f\u77e5\u7684\u53cd\u61c9\u662f\u4f2f\u5947\u9084\u539f\u53cd\u61c9\uff0c\u5176\u5177\u6709\u5ee3\u6cdb\u7684\u61c9\u7528\u6027\uff0c\u6700\u91cd\u8981\u7684\u61c9\u7528\u662f\u5728\u53e3\u670d\u907f\u5b55\u85e5\uff08oral contraceptives\uff09\u7684\u5408\u6210\uff0c\u56e0\u6b64\u4f2f\u5947\u53c8\u6709\u85e5\u4e38\u4e4b\u7236\u7684\u7a31\u865f\u3002\u4f2f\u5947\u7684\u805a\u916e\u985e\u7406\u8ad6\uff08Polyketide Theory\uff09\uff0c\u5728\u751f\u7269\u5408\u6210\u4e2d\u4ee5\u53ca\u5929\u7136\u7269\u4e2d\u4e5f\u88ab\u4eba\u719f\u77e5\u3002\u53e6\u5916\uff0c\u4ed6\u6700\u5f8c\u767c\u8868\u7684\u7814\u7a76–\u5408\u6210\u4e8c\u70ef\u4e09\u7fb0\u9435\u884d\u751f\u7269\uff08diene iron tricarbonyl derivatives\uff09\uff0c\u5f8c\u4f86\u4e5f\u88ab\u64f4\u5c55\u61c9\u7528\u30021,4<\/sup><\/p>\n

\u57281930\u5e74\u4ee3\u70ba\u4e86\u89e3\u6c7a\u5177\u985e\u56fa\u9187\u7d50\u69cb\u3001\u5177\u82b3\u9999\u74b0\u7d50\u69cb\u7684\u6fc0\u7d20\u4ee5\u53ca\u8102\u74b0\u5316\u5408\u7269\uff08alicyclic compound\uff09\u56e0\u70ba\u5408\u6210\u9019\u4e9b\u5316\u5408\u7269\u7684\u6280\u8853\u9084\u4e0d\u5920\u6210\u719f\u3001\u4e14\u5728\u7acb\u9ad4\u9078\u64c7\u6027\u4e0a\u4ecd\u6709\u56f0\u96e3\u7684\u554f\u984c\uff0c\u4f2f\u5947\u5229\u7528\u91d1\u5c6c\u9209\u8207\u9187\u985e\u53cd\u61c9\uff0c\u5c07\u916f\u985e\u9084\u539f\u6210\u9187\u985e\u3001\u751a\u81f3\u9084\u539f\u8418\u985e\uff0c\u4f46\u6c92\u8fa6\u6cd5\u6709\u6548\u9084\u539f\u82ef\u3002\u5c0d\u65bc\u9084\u539f\u904e\u7a0b\u6bd4\u8f03\u5e38\u7528\u4e00\u4e9b\u50ac\u5316\u5291\u3001\u6216\u662f\u9ad8\u6eab\u9ad8\u58d3\u65b9\u5f0f\u4f86\u9084\u539f\u7684\u65b9\u6cd5\uff08\u4f8b\u5982\uff1a\u5229\u7528\u9251\u914d\u5408\u5927\u91cf\u7684\u6c2b\u6c23\u3001\u93b3\u6216\u9285-\u927b\u50ac\u5316\u5291\u662f\u4e00\u822c\u5e38\u7528\u7684\u65b9\u6cd5\uff09\uff0c\u6703\u4f7f\u5f97\u7522\u7269\u7acb\u9ad4\u9078\u64c7\u6027\u7684\u6539\u8b8a\uff0c\u6216\u662f\u6703\u79fb\u53bb\u4e00\u4e9b\u5b98\u80fd\u57fa\u3002\u7576\u6642\u5728\u985e\u56fa\u9187\u7684\u5408\u6210\u4e2d\u4e5f\u9047\u5230\u554f\u984c\uff0c\u56e0\u7576\u6642\u9084\u4e0d\u77e5\u9053\u4e59\u70ef\u57fa\u919a\u5728\u9178\u4e2d\u5bb9\u6613\u6c34\u89e3\u5f97\u5230\u7fb0\u57fa\u5316\u5408\u7269\u3002\u5230\u4e861943\u5e74\uff0c\u4f2f\u5947\u6709\u4e86\u4e00\u500b\u91cd\u8981\u767c\u73fe\uff1a\u7576\u5728\u6db2\u9ad4\u6c28\u8207\u91d1\u5c6c\u9209\u548c\u9187\u5728\u540c\u4e00\u53cd\u61c9\u4e2d\u53ef\u4ee5\u6709\u9084\u539f\u7684\u6548\u679c\uff0c\u82e5\u662f\u5728\u6c92\u6709\u53d6\u4ee3\u57fa\u7684\u82b3\u9999\u74b0\u4e0a\u53ef\u4ee5\u589e\u52a0\u5169\u500b\u6c2b\u539f\u5b50\uff08\u610f\u6307\u82b3\u9999\u74b0\u53ef\u4ee5\u88ab\u9084\u539f\uff09\uff1b\u53e6\u4e00\u5247\u662f\u53ef\u4ee5\u5f88\u5bb9\u6613\u5f9e\u4e59\u70ef\u57fa\u919a\u5316\u5408\u7269\u5f97\u5230\u7fb0\u57fa\u5316\u5408\u7269\u3002\u4f2f\u5947\u7d50\u5408\u9019\u5169\u500b\u767c\u73fe\u8a2d\u8a08\u51fa\u5be6\u9a57\uff1a\u9996\u5148\u4ed6\u5c07\u7532\u6c27\u57fa\u82ef(1<\/strong>)\u5229\u7528\u6db2\u9ad4\u6c28\u8207\u91d1\u5c6c\u9209\u548c\u9187\u9032\u884c\u9084\u539f\u53cd\u61c9\uff0c\u5f97\u52302,5-\u4e8c\u6c2b\u884d\u751f\u7269(2<\/strong>)\uff0c\u518d\u5c07\u884d\u751f\u7269(2<\/strong>)\u5728\u9178\u6027\u689d\u4ef6\u4e0b\u9032\u884c\u6c34\u89e3\u5f97\u5230\u74b0\u5df1-3-\u70ef-1-\u916e(3<\/strong>)\uff0c\u4e26\u53ef\u5728\u9178\u50ac\u5316\u4e4b\u4e0b\u518d\u9032\u884c\u7570\u69cb\u5316\u5f97\u5230\u7522\u7269\u4ee5\u74b0\u5df1-2-\u70ef-1-\u916e(4<\/strong>)\u30021,4<\/sup>\uff08\u5716\u4e8c\uff09<\/p>\n

\"64413_p2\"<\/a>

\u5716\u4e8c \u4f2f\u5947\u9084\u539f\u53cd\u61c9\u53ef\u5c07\u7532\u6c27\u57fa\u82ef\u9084\u539f\u3001\u5408\u6210\u5316\u5408\u7269(2)\u3001(3)\u3001(4) \uff08\u4f86\u6e90\uff1a\u4f5c\u8005\u7e6a\u88fd\uff09<\/p><\/div>\n

\u74b0\u5df1\u70ef\u916e\uff08cyclohexenone\uff09\u7684\u884d\u751f\u7269\u662f\u5f88\u591a\u985e\u56fa\u9187\u6fc0\u7d20\u4e2d\u6240\u542b\u6709\u7684\u7d50\u69cb\uff0c\u6b64\u5916\u9019\u500b\u7d50\u69cb\u5728\u5176\u4ed6\u7684\u5408\u6210\u4e2d\u4e5f\u5f88\u5e38\u626e\u6f14\u8457\u4e2d\u9593\u9ad4\u7684\u89d2\u8272\u3002\u4f2f\u5947\u57281944\u52301950\u5e74\u9593\u5728\u5316\u5b78\u671f\u520a\u4e0a\u767c\u8868\u4e86\u6709\u95dc\u6b64\u7814\u7a76\u7684\u4e00\u7cfb\u5217\u6587\u7ae0\uff0c\u9019\u4e9b\u6587\u7ae0\u66f4\u662f\u5960\u5b9a\u4e86\u9019\u4e00\u7cfb\u5217\u5316\u5408\u7269\u5728\u5408\u6210\u4e0a\u7684\u57fa\u790e\u3002\u4f2f\u5947\u4e5f\u63a8\u6e2c\u51fa\u5b83\u7684\u53cd\u61c9\u6a5f\u69cb\u4ee5\u53ca\u53d6\u4ee3\u57fa\u4e0d\u540c\u6642\u6240\u9020\u6210\u7684\u5f71\u97ff\u3002<\/p>\n

\u8209\u4f8b\u4ee5\u82ef\u74b0\u7684\u4f8b\u5b50\u6240\u7e6a\u88fd\u7684\u53cd\u61c9\u6a5f\u69cb2,3,5<\/sup>\uff1a\u5148\u5229\u7528\u82ef\uff08A<\/strong>\uff09\u8207\u9209\u9032\u884c\u96fb\u5b50\u8f49\u79fb\u5f97\u5230\u5f97\u4e00\u96fb\u5b50\u7684\u4e2d\u9593\uff08C<\/strong>\uff09\uff0c\u518d\u8207\u7532\u9187\u9032\u884c\u8cea\u5b50\u8f49\u79fb\u5f97\u5230\uff08D<\/strong>\uff09\uff1b\u4e2d\u9593\u9ad4\uff08D<\/strong>\uff09\u518d\u8207\u91d1\u5c6c\u9209\u9032\u884c\u4e00\u6b21\u96fb\u5b50\u8f49\u79fb\u5f97\u4e2d\u9593\u9ad4\uff08E<\/strong>\uff09\uff0c\u6700\u5f8c\u518d\u8207\u7532\u9187\u9032\u884c\u8cea\u5b50\u8f49\u79fb\u5f97\u5230\u9084\u539f\u7522\u7269\uff08B<\/strong>\uff09\u3002\uff08\u5716\u4e09\uff09<\/p>\n

\"64413_p3\"<\/a>

\u5716\u4e09 \u4ee5\u82ef\u74b0\u7684\u4f8b\u5b50\u7684\u4f2f\u5947\u9084\u539f\u53cd\u61c95\uff08\u4f86\u6e90\uff1a\u4f5c\u8005\u7e6a\u88fd\uff09<\/p><\/div>\n

\u5728\u82ef\u74b0\u4e0a\u82e5\u6539\u63a5\u4e0d\u540c\u53d6\u4ee3\u57fa\u4e5f\u6703\u6709\u4e0d\u540c\u6548\u679c\u3002\u4e0b\u5716\u70ba\u63a5\u4e0a\u62c9\u96fb\u5b50\u57fa\u5718\uff08\u5716\u56db\uff09\u4ee5\u53ca\u63a8\u96fb\u5b50\u57fa\u5718\uff08\u5716\u4e94\uff09\u7684\u53cd\u61c9\u6a5f\u69cb\u3002<\/p>\n

\"64413_p4\"<\/a>

\u5716\u56db \u82ef\u74b0\u4e0a\u6709\u62c9\u96fb\u5b50\u57fa\u5718\u53d6\u4ee3\uff08\u4f86\u6e90\uff1a\u53c3\u8003\u8cc7\u65998\uff09<\/p><\/div>\n

\"64413_p5\"<\/a>

\u5716\u4e94 \u82ef\u74b0\u4e0a\u6709\u63a8\u96fb\u5b50\u57fa\u5718\u53d6\u4ee3\uff08\u4f86\u6e90\uff1a\u53c3\u8003\u8cc7\u65998\uff09<\/p><\/div>\n

\u8209\u4f8b\u4f86\u8aaa\uff0c\u82e5\u82ef\u74b0\u63a5\u4e0a\u62c9\u96fb\u5b50\u63a5\u5718\uff0c\u82ef\u7532\u9178(I<\/strong>)\u5728\u63a5\u53d7\u96fb\u5b50\u5f8c\u53ef\u4ee5\u5f62\u6210\u4e2d\u9593\u9ad4(II<\/strong>)\u6216\u662f\u4e2d\u9593\u9ad4(III<\/strong>)\uff0c\u800c\u4e2d\u9593\u9ad4(III<\/strong>)\u53ef\u4ee5\u6709\u4e00\u8f03\u7a69\u5b9a\u7d50\u69cb\u7684\u5171\u632f\u5f0f-\u4e2d\u9593\u9ad4(IV)\uff1b\u56e0\u6b64\u5728\u63a5\u4e0a\u62c9\u96fb\u5b50\u57fa\u5718\u6642\uff0c\u53cd\u61c9\u4fbf\u6703\u6bd4\u8f03\u8da8\u5411\u65bc\u4ee5\u4e0b\u9019\u689d\u8def\u5f91\uff0c\u4ee5\u5f62\u6210\u66f4\u591a\u7a69\u5b9a\u7684\u5171\u632f\u4e2d\u9593\u9ad4\u3002\uff08\u5716\u516d\uff09<\/p>\n

\"64413_p6\"<\/a>

\u5716\u516d \u62c9\u96fb\u5b50\u57fa\u5718\u7684\u5f71\u97ff7\uff08\u4f86\u6e90\uff1a\u4f5c\u8005\u7e6a\u88fd\uff09<\/p><\/div>\n

\u800c\u82ef\u74b0\u4e0a\u82e5\u63a5\u4e0a\u63a8\u96fb\u5b50\u63a5\u5718\uff0c\u5982\u5716\u4e03\uff1a\u82ef\u7532\u919a(V<\/strong>)\u5728\u63a5\u53d7\u96fb\u5b50\u5f8c\u53ef\u4ee5\u5f62\u6210\u4e2d\u9593\u9ad4(VI<\/strong>)\u53ca\u4e2d\u9593\u9ad4(VII<\/strong>)\uff0c\u7531\u65bc\u63a8\u96fb\u5b50\u6548\u61c9\u7684\u95dc\u4fc2\uff0c\u4e2d\u9593\u9ad4(VII<\/strong>)\u96fb\u5b50\u96f2\u5bc6\u5ea6\u8f03\u9ad8\u3001\u7522\u751f\u8f03\u5927\u7684\u65a5\u529b\uff0c\u56e0\u6b64\u4e2d\u9593\u9ad4(VI)\u7684\u7d50\u69cb\u76f8\u5c0d\u65bc\u4e2d\u9593\u9ad4(VII<\/strong>)\u7a69\u5b9a\u3002<\/p>\n

\"64413_p7\"<\/a>

\u5716\u4e03 \u63a8\u96fb\u5b50\u57fa\u5718\u7684\u5f71\u97ff7\uff08\u4f86\u6e90\uff1a\u4f5c\u8005\u7e6a\u88fd\uff09<\/p><\/div>\n

\u7531\u4ee5\u4e0a\u5171\u632f\u4e2d\u9593\u9ad4\u8207\u82ef\u74b0\u4e0a\u7684\u63a8\u62c9\u96fb\u5b50\u53d6\u4ee3\u57fa\u4e4b\u95dc\u4fc2\uff0c\u5176\u5f71\u97ff\u7d50\u679c\u53ef\u7531\u5716\u516b\u4f5c\u70ba\u7e3d\u7d50\u3002<\/p>\n

\"64413_p8\"<\/a>

\u5716\u516b \u63a8\u62c9\u96fb\u5b50\u57fa\u5718\u7684\u5f71\u97ff\u4e4b\u7d50\u679c\uff0cEDG \u8868\u793a\u63a8\u96fb\u5b50\u57fa\u5718\uff0cEWG\u8868\u793a\u62c9\u96fb\u5b50\u57fa\u5718\uff08\u4f86\u6e90\uff1a\u53c3\u8003\u8cc7\u65992,3\uff09<\/p><\/div>\n

\n

\u53c3\u8003\u6587\u737b<\/b><\/strong><\/p>\n

    \n
  1. Obituary- Arthur John Birch, http:\/\/oa.anu.edu.au\/obituary\/birch-arthur-john-109<\/li>\n
  2. Birch reduction ~ Named reaction.com, http:\/\/www.name-reaction.com\/birch-reduction<\/li>\n
  3. Birch reduction, http:\/\/www.organic-chemistry.org\/namedreactions\/birch-reduction.shtm<\/li>\n
  4. Rickards, R. W., & Cornforth, J. (1995). Arthur John Birch. 3 August 1915.<\/li>\n
  5. http:\/\/www.columbia.edu\/itc\/chemistry\/c3045\/client_edit\/ppt\/PDF\/11_10_11.pdf<\/li>\n
  6. http:\/\/www.ch.imperial.ac.uk\/rzepa\/blog\/?p=8452<\/li>\n
  7. Organic Reactions Stereochemistry And Mechanism (Through Solved Problems), By P S Kalsi<\/li>\n
  8. Zimmerman, H. E., & Wang, P. A. (1993). The regioselectivity of the Birch reduction.\u00a0Journal of the American Chemical Society<\/em>,\u00a0115<\/em>(6), 2205-2216.<\/li>\n<\/ol>\n<\/div>","protected":false},"excerpt":{"rendered":"

    \u4f2f\u5947\u9084\u539f\u53cd\u61c9 (Brich Reduction) \u570b\u7acb\u81fa\u7063\u5e2b\u7bc4\u5927\u5b78\u5316\u5b78\u7cfb\u78a9\u58eb\u73ed \u937e\u9577\u5fd7 Arthur John…<\/p>\n","protected":false},"author":50,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[108,4798,4800],"tags":[9005,9006,1209,7315,5553,1208],"class_list":["post-64413","post","type-post","status-publish","format-standard","hentry","category-chemistry00","category-chemistry07","category-chemistry07-02","tag-named-reaction","tag-reduction","tag-sodium","tag-7315","tag-5553","tag-1208","loop-entry","cat-108","cat-4798","cat-4800","no-thumbnail"],"views":4268,"_links":{"self":[{"href":"http:\/\/localhost\/wp-json\/wp\/v2\/posts\/64413","targetHints":{"allow":["GET"]}}],"collection":[{"href":"http:\/\/localhost\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"http:\/\/localhost\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"http:\/\/localhost\/wp-json\/wp\/v2\/users\/50"}],"replies":[{"embeddable":true,"href":"http:\/\/localhost\/wp-json\/wp\/v2\/comments?post=64413"}],"version-history":[{"count":1,"href":"http:\/\/localhost\/wp-json\/wp\/v2\/posts\/64413\/revisions"}],"predecessor-version":[{"id":86442,"href":"http:\/\/localhost\/wp-json\/wp\/v2\/posts\/64413\/revisions\/86442"}],"wp:attachment":[{"href":"http:\/\/localhost\/wp-json\/wp\/v2\/media?parent=64413"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"http:\/\/localhost\/wp-json\/wp\/v2\/categories?post=64413"},{"taxonomy":"post_tag","embeddable":true,"href":"http:\/\/localhost\/wp-json\/wp\/v2\/tags?post=64413"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}