{"id":33474,"date":"2020-07-14T08:00:38","date_gmt":"2020-07-14T00:00:38","guid":{"rendered":"\/\/www.gsbet888.com\/?p=33474"},"modified":"2020-07-09T10:37:51","modified_gmt":"2020-07-09T02:37:51","slug":"heck-matsuda%e5%8f%8d%e5%ba%94%ef%bc%88%e4%b8%80%ef%bc%89","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2020\/07\/heck-matsuda%e5%8f%8d%e5%ba%94%ef%bc%88%e4%b8%80%ef%bc%89.html","title":{"rendered":"Heck-Matsuda\u53cd\u5e94\uff08\u4e00\uff09"},"content":{"rendered":"
1977\u5e74\u65e5\u672cKyushu\u5927\u5b66\u7684Matsuda (\u677e\u7530 \u6634,\u4e5d\u5dde\u5927\u5b66\u5de5\u5b66\u90e8\u5408\u6210\u5316\u5b66\u79d1, Matsuda Tsutomu, Department of Organic Synthesis, Faculty of Engineering, Kyushu University)\u7814\u7a76\u5ba4\u9996\u6b21\u62a5\u9053\u4e86\u7531\u94af\u50ac\u5316\u5242\u4fc3\u8fdb\u7684\u6c2f\u5316\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e\u5404\u7c7b\u4f9b\u7535\u5b50\u57fa\u56e2\u53d6\u4ee3\u70ef\u70c3\u4e4b\u95f4\u7684\u4ea4\u53c9\u5076\u8054\u8fc7\u7a0b\uff0c\u6210\u529f\u5b9e\u73b0\u76f8\u5e94\u4f9b\u7535\u5b50\u57fa\u53d6\u4ee3\u70ef\u70c3\u7684\u82b3\u57fa\u5316[1]<\/sup>\u3002\u8be5\u53cd\u5e94\u6761\u4ef6\u5bf9\u4e8e\u82ef\u4e59\u70ef\u5e95\u7269\u5177\u6709\u8f83\u597d\u7684(E)-\u9009\u62e9\u6027\uff0c\u7136\u800c\uff0c\u53cd\u5e94\u4ea7\u7387\u4e2d\u7b49\u3002<\/p>\n \u4e4b\u540e\uff0cMatsuda\u91c7\u7528\u56db\u6c1f\u787c\u9178\u82b3\u9999\u91cd\u6c2e\u76d0\uff0c\u5c06\u5e95\u7269\u6269\u5c55\u81f3\u4e59\u70ef\uff0c\u5e76\u6210\u529f\u5b9e\u73b04\u02b9-\u4e59\u70ef\u57fa\u82ef\u5e76-15-\u51a0-5\u7684\u5408\u6210[2]<\/sup>\u3002<\/p>\n 1979\u5e74\uff0cMatsuda\u5bf9\u5176\u5b83\u56db\u6c1f\u787c\u9178\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e\u4e59\u70ef\u7684\u5076\u8054\u53cd\u5e94\u8fdb\u884c\u8fdb\u4e00\u6b65\u7814\u7a76\uff0c\u987a\u5229\u5b8c\u6210\u5404\u7c7b\u53d6\u4ee3\u82ef\u4e59\u70ef\u7684\u5408\u6210[3]<\/sup>\u3002<\/p>\n 1980\u5e74\uff0cMatsuda\u7814\u7a76\u53d1\u73b0\uff0c\u901a\u8fc7\u82b3\u80fa\u4e0e\u4e9a\u785d\u9178\u53d4\u4e01\u916f\u539f\u4f4d\u751f\u6210\u7684\u82b3\u9999\u91cd\u6c2e\u76d0\u5728\u94af\u50ac\u5316\u5242\u5b58\u5728\u4e0b\uff0c\u4e0e\u70ef\u57fa\u5316\u5408\u7269\u53cd\u5e94\uff0c\u540c\u6837\u53ef\u4ee5\u6709\u6548\u5b8c\u6210\u70ef\u70c3\u7684(E)-\u9009\u62e9\u6027\u82b3\u57fa\u5316\u3002\u540c\u65f6\uff0c\u8fd8\u80fd\u591f\u4f7f\u53cd\u5e94\u4ea7\u7387\u83b7\u5f97\u8f83\u5927\u63d0\u9ad8[4]<\/sup>\u3002<\/p>\n 1981\u5e74\uff0cMatsuda\u5bf9\u8102\u80aa\u65cf\u70ef\u70c3\uff0c\u73af\u70ef\u70c3\u3001\u70ef\u4e19\u9187\u3001\u82ef\u4e59\u70ef\u53ca\u4e19\u70ef\u9178\u4e59\u916f\u7b49\u5404\u7c7b\u70ef\u57fa\u5e95\u7269\u4e0e\u82b3\u9999\u91cd\u6c2e\u76d0\u4e4b\u95f4\u7684\u5076\u8054\u53cd\u5e94\u8fdb\u884c\u4e86\u6df1\u5165\u7814\u7a76\uff0c\u53d1\u73b0\u5728\u94af\u50ac\u5316\u6761\u4ef6\u4e0b\uff0c\u80fd\u591f\u8f83\u4e3a\u65b9\u4fbf\u5730\u5b9e\u73b0\u4e0a\u8ff0\u5e95\u7269\u7684(E)-\u9009\u62e9\u6027\u82b3\u57fa\u5316[5]<\/sup>\u3002<\/p>\n 1984\u5e74\uff0cKikukawa (\u83ca\u5ddd\u3000\u6e05, \u4e5d\u5dde\u5927\u5b66\u5de5\u5b66\u90e8\u5408\u6210\u5316\u5b66\u79d1, Kikukawa Kiyoshi, Department of Organic Synthesis, Faculty of Engineering, Kyushu University)\u5c06Matsuda\u53d1\u5c55\u7684\u5076\u8054\u65b9\u6cd5\u5b66\u5e94\u7528\u4e8e\u4e59\u70ef\u57fa\u4e09\u7532\u57fa\u7845\u70f7\u7684(E)-\u9009\u62e9\u6027\u82b3\u57fa\u5316[6]<\/sup>\u3002<\/p>\n \u4e4b\u540e\uff0cKikukawa\u8fdb\u4e00\u6b65\u5bf9\u94af\u50ac\u5316\u6761\u4ef6\u4e0b\uff0c(E)-\u82ef\u4e59\u70ef\u57fa\u4e09\u7532\u57fa\u7845\u70f7\u53ca(Z)-\u82ef\u4e59\u70ef\u57fa\u4e09\u7532\u57fa\u7845\u70f7\u4e0e\u82b3\u57fa\u91cd\u6c2e\u76d0\u7684\u5076\u8054\u53cd\u5e94\u8fdb\u884c\u4e86\u7cfb\u7edf\u7814\u7a76\uff0c\u53d1\u73b0\u4e8c\u8005\u5747\u83b7\u5f97(E)-\u9009\u62e9\u6027\u82b3\u57fa\u5316\u4ea7\u7269[7]<\/sup>\u3002<\/p>\n \u540c\u65f6\uff0cKikukawa\u4e0eIkenaga (\u6c60\u6c38\u3000\u548c\u654f,\u718a\u672c\u5de5\u696d\u5927\u5b66\u5de5\u696d\u5316\u5b66\u79d1,Ikenaga Kazutoshi, Department of Industrial Chemistry, Kumamoto Institute of Technology)\u5bf9\u5176\u5b83\u7c7b\u578b\u7684\u82ef\u4e59\u70ef\u57fa\u4e09\u70f7\u57fa\u7845\u70f7\u4e0e\u82b3\u9999\u91cd\u6c2e\u76d0\u5076\u8054\u8fc7\u7a0b\u7684\u8fdb\u4e00\u6b65\u7814\u7a76\uff0c\u8868\u660e\u91c7\u7528\u5927\u4f4d\u963b\u70f7\u57fa\u53d6\u4ee3\u7684\u7845\u70f7\u5e95\u7269\uff0c\u53ef\u4ee5\u83b7\u5f97\u66f4\u9ad8\u7a0b\u5ea6\u7684\u7acb\u4f53\u9009\u62e9\u6027[8]<\/sup>\u3002<\/p>\n 1985\u5e74\uff0cKikukawa\u8fdb\u4e00\u6b65\u5c06N-\u4e9a\u785d\u57fa-N-\u82b3\u57fa\u4e59\u9170\u80fa\u5f02\u6784\u5316\u539f\u4f4d\u751f\u6210\u7684\u82b3\u9999\u91cd\u6c2e\u76d0\uff0c\u5e94\u7528\u4e8e\u70ef\u70c3\u3001\u53d6\u4ee3\u70ef\u70c3\u53ca\u73af\u70ef\u70c3\u7684(E)-\u9009\u62e9\u6027\u82b3\u57fa\u5316[9]<\/sup>\u3002<\/p>\n 1986\u5e74\uff0cKikukawa\u7814\u7a76\u4e86\u94af\u50ac\u5316\u5242\u6761\u4ef6\u4e0b\uff0c\u5404\u7c7b\u03b1-\u82ef\u4e59\u70ef\u57fa\u9521\u70f7\u4e0e\u82b3\u9999\u91cd\u6c2e\u76d0\u7684\u5076\u8054\u53cd\u5e94\uff0c\u610f\u5916\u5730\u53d1\u73b0\u53cd\u5e94\u8fc7\u7a0b\u4e2d\uff0c\u7acb\u4f53\u9009\u62e9\u6027\u53d1\u751f\u7ffb\u8f6c\uff0c\u83b7\u5f97(Z)-\u4e8c\u82b3\u57fa\u4e59\u70ef[10]<\/sup>\u3002<\/p>\n 1995\u5e74\uff0cM. Beller\u901a\u8fc7\u5408\u6210\u4e2d\u5e38\u7528\u7684Pd\/C\u3001Pd\/BaSO4<\/sub>\u53caPd\/Al2<\/sub>O3<\/sub>\u50ac\u5316\u5242\uff0c\u5b8c\u6210\u9996\u4f8b\u7531\u5f02\u76f8\u94af\u50ac\u5316\u5242\u53c2\u4e0e\u7684\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e\u70ef\u57fa\u5316\u5408\u7269\u4e4b\u95f4\u7684\u4ea4\u53c9\u5076\u8054\u53cd\u5e94[11]<\/sup>\u3002\u540c\u65f6\uff0cM. Beller\u60ca\u559c\u5730\u53d1\u73b0\uff0c\u7531\u4e0a\u8ff0\u5f02\u76f8\u50ac\u5316\u5242\u53c2\u4e0e\u7684\u5076\u8054\u8fc7\u7a0b\u53ef\u4ee5\u5728\u9187\u7c7b\u6eb6\u5242\u4e2d\u987a\u5229\u8fdb\u884c\u3002<\/p>\n 1999\u5e74\uff0cJ. P. Gen\u00eat\u5c06\u70ef\u57fa\u5e95\u7269\u6269\u5c55\u81f3\u4e59\u70ef\u57fa\u4e09\u6c1f\u787c\u9178\u94be\uff0c\u4ee5\u826f\u597d\u7684\u4ea7\u7387\u5b8c\u6210\u82ef\u4e59\u70ef\u7684\u5408\u6210[12]<\/sup>\u3002<\/p>\n 2000\u5e74\uff0cF. Naso\u91c7\u7528\u4e09\u6c2f\u5316\u787c\u539f\u4f4d\u8f6c\u91d1\u5c5e\u5316\u5f62\u6210\u7684\u70ef\u57fa\u787c\u8bd5\u5242\u4e0e\u82b3\u9999\u91cd\u6c2e\u76d0\u8fdb\u884c\u7684\u4ea4\u53c9\u5076\u8054\u53cd\u5e94\uff0c\u6210\u529f\u5b8c\u6210\u82b3\u57fa\u4e59\u70ef\u7684\u5408\u6210\u3002\u8be5\u65b9\u6cd5\u5177\u6709\u9ad8\u5ea6\u7684\u533a\u57df\u53ca\u7acb\u4f53\u9009\u62e9\u6027[13]<\/sup>\u3002<\/p>\n \u6587\u732e\u4e2d\u5c06\u8fd9\u79cd\u94af\u50ac\u5316\u5242\u53c2\u4e0e\u7684\u82b3\u9999\u91cd\u6c2e\u76d0\u4e0e\u5404\u7c7b\u70ef\u57fa\u5316\u5408\u7269\u4e4b\u95f4\u7684\u4ea4\u53c9\u5076\u8054\u8fc7\u7a0b\uff0c\u5f62\u6210\u82b3\u57fa\u70ef\u70c3\u6216\u82b3\u57fa\u53d6\u4ee3\u7684\u03b1, \u03b2-\u4e0d\u9971\u548c\u5316\u5408\u7269\u7684\u53cd\u5e94\u79f0\u4e3aHeck-Matsuda\u53cd\u5e94 (Heck-Matsuda reaction)\u6216Matsuda\u53cd\u5e94 (Matsuda reaction)\u6216Heck-Matsuda\u82b3\u57fa\u5316 (Heck-Matsuda arylation)\u3002\u8be5\u53cd\u5e94\u662f\u5bf9Heck-Mizoroki (\u6e9d\u5442\u6728 \u52c9,\u6771\u4eac\u5de5\u696d\u5927\u5b66\u8cc7\u6e90\u5316\u5b66\u7814\u7a76\u6240,Mizoroki Tsutomu, Research laboratory of Resources Utilization, Tokyo Institute of \u00a0Techonology)\u53cd\u5e94\u7684\u6709\u529b\u8865\u5145\u3002\u540c\u65f6\uff0c\u8be5\u65b9\u6cd5\u5b66\u4e0eMeerwein\u82b3\u57fa\u5316\u53cd\u5e94 (Meerwein arylation)\u5f62\u6210\u4e92\u8865[1]<\/sup>\u3002\u76ee\u524d\uff0c\u8be5\u53cd\u5e94\u5df2\u7ecf\u5e7f\u6cdb\u5e94\u7528\u4e8e\u5404\u7c7b\u70ef\u57fa\u5316\u5408\u7269\u4e2d\u53cc\u952e\u7684\u82b3\u57fa\u5316[1]-[19]<\/sup>\u3001\u5404\u7c7b\u7cd6\u82f7[20]-[22]<\/sup>\u3001\u836f\u7269[23]-[25]<\/sup>\u53ca\u5929\u7136\u4ea7\u7269\u5168\u5408\u6210[26]-[35]<\/sup>\u7684\u5173\u952e\u6b65\u9aa4\u3002\u7531\u4e8e\u7bc7\u5e45\u9650\u5236\uff0c\u5bf9\u4e8e\u8be5\u53cd\u5e94\u7684\u76f8\u5173\u7814\u7a76\u8fdb\u5c55\uff0c\u5c0f\u7f16\u5c06\u5728\u4e0b\u4e00\u671f\u8fdb\u884c\u8be6\u7ec6\u4ecb\u7ecd\u3002<\/p>\n \u70ef\u70c3\u53c2\u4e0e\u7684<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong>[1]-[7], [11]-[12]<\/sup><\/p>\n \u4e59\u70ef\u57fa\u4e09\u7532\u57fa\u7845\u70f7\u53c2\u4e0e\u7684<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong>[8]<\/sup><\/p>\n N-<\/strong>\u4e9a\u785d\u57fa<\/strong>-N-<\/strong>\u82b3\u57fa\u4e59\u9170\u80fa\u5f02\u6784\u5316\u539f\u4f4d\u751f\u6210\u82b3\u9999\u91cd\u6c2e\u76d0<\/strong>[9]<\/sup><\/p>\n \u03b1-<\/strong>\u82ef\u4e59\u70ef\u57fa\u9521\u70f7\u53c2\u4e0e\u7684<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong>[10]<\/sup><\/p>\n \u5171\u8f6d\u805a\u5408\u7269\u7684\u5408\u6210[1]-[2]<\/sup><\/p>\n (R)-tolterodine\u7684\u5408\u6210[3]<\/sup><\/p>\n \u82b3\u57faC-\u7cd6\u82f7\u7684\u5408\u6210[4]<\/sup><\/p>\n \u82b3\u57faSF5<\/sub>\u5316\u5408\u7269\u7684\u5408\u6210[5]<\/sup><\/p>\n \u70ef\u57fa\u5316\u5408\u7269\u53c2\u4e0e\u7684<\/strong>Heck-Matsuda<\/strong>\u53cd\u5e94<\/strong><\/span><\/p>\n \u5ba4\u6e29\u4e0b\uff0c\u5411\u94af\u50ac\u5316\u5242 (0.02 eq.)\u3001\u4e59\u9178\u94a0 (3 eq.)\u3001\u70ef\u57fa\u5316\u5408\u7269(2 eq.)\u7684\u4e59\u8148\u6eb6\u6db2 (\u6d53\u5ea6\u4e3a 0.625M)\u4e2d\u52a0\u5165\u56db\u6c1f\u787c\u9178\u82b3\u9999\u91cd\u6c2e\u76d0 (1 eq.)\uff0c\u5c06\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u8fdb\u884c\u6405\u62cc\u3002\u6b64\u65f6\uff0c\u89c2\u5bdf\u5230\u6709\u5927\u91cf\u6c14\u4f53 (\u6c2e\u6c14)\u4ea7\u751f\u3002\u5f53\u6c14\u4f53\u4e0d\u518d\u4ea7\u751f\u65f6\uff0c\u5411\u4e0a\u8ff0\u53cd\u5e94\u6df7\u5408\u7269\u4e2d\u52a0\u5165\u9971\u548c\u78b3\u9178\u94a0\u6eb6\u6db2\uff0c\u518d\u7ee7\u7eed\u6405\u62cc1h\u3002\u968f\u540e\uff0c\u52a0\u5165\u9002\u91cf\u4e59\u919a\u8fdb\u884c\u8403\u53d6\u3002\u5c06\u5408\u5e76\u7684\u6709\u673a\u76f8\u4f9d\u6b21\u901a\u8fc7\u9971\u548c\u6c2f\u5316\u94a0\u6eb6\u6db2\u6d17\u6da4\u4e0e\u65e0\u6c34\u786b\u9178\u9541\u5e72\u71e5\u3002\u51cf\u538b\u9664\u53bb\u6eb6\u5242\u540e\uff0c\u5c06\u7c97\u4ea7\u7269\u901a\u8fc7\u7845\u80f6\u67f1\u8272\u8c31\u6216\u901a\u8fc7\u51cf\u538b\u84b8\u998f\u8fdb\u884c\u7eaf\u5316\uff0c\u83b7\u5f97\u76f8\u5e94\u5076\u8054\u4ea7\u7269\u3002<\/p>\n<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
\u57fa\u672c\u6587\u732e<\/strong><\/h4>\n
\n
\u53cd\u5e94\u673a\u7406<\/strong><\/h4>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
\u53c2\u8003\u6587\u732e<\/strong><\/h4>\n
\n
\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/h4>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
<\/a><\/p>\n
\u5b9e\u9a8c\u6b65\u9aa4<\/strong><\/h4>\n
\u53c2\u8003\u6587\u732e<\/strong><\/h4>\n
\n