{"id":13442,"date":"2017-03-29T09:45:15","date_gmt":"2017-03-29T01:45:15","guid":{"rendered":"\/\/www.gsbet888.com\/?p=13442"},"modified":"2019-08-02T18:53:27","modified_gmt":"2019-08-02T10:53:27","slug":"passerini%e5%8f%8d%e5%ba%94","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2017\/03\/passerini%e5%8f%8d%e5%ba%94.html","title":{"rendered":"Passerini\u53cd\u5e94"},"content":{"rendered":"

<\/p>\n

\u6982\u8ff0<\/h4>\n

\u5f02\u8148\u662f\u4e00\u7c7b\u72ec\u7279\u7684\u6709\u673a\u7269\uff0c\u53ef\u4ee5\u540c\u65f6\u4e0e\u4eb2\u7535\u8bd5\u5242\u3001\u4eb2\u6838\u8bd5\u5242\u53cd\u5e94\u3002\u5f02\u8148\u5728\u5408\u6210\u4e0a\u6709\u7528\u9014\u7684\u7b2c\u4e00\u4e2a\u53cd\u5e94\u662f\u7531M.Passerini\u62a5\u9053\u7684\uff0c\u4ed6\u63d0\u51fa\u5f02\u8148\u548c\u7fa7\u9178\u8fd8\u6709\u7fb0\u57fa\u5316\u5408\u7269(\u919b\u6216\u916e)\u4e00\u6b65\u53cd\u5e94\u53ef\u5f97\u5230-\u9170\u6c27\u57fa\u9170\u80fa\uff0c\u4e5f\u5c31\u662f\u73b0\u5728\u6240\u719f\u77e5\u7684Passerini multicomponent reaction(MCR)\u3002[1]<\/sup><\/p>\n

\u7279\u70b9<\/h4>\n

Passerini\u53cd\u5e94\u5177\u6709\u5982\u4e0b\u51e0\u4e2a\u7279\u5f81\uff1a<\/p>\n

\u2460\u539f\u5b50\u5229\u7528\u7387\u9ad8\uff0c\u60f0\u6027\u975e\u6781\u6027\u6eb6\u5242\u6709\u5229\u4e8e\u53cd\u5e94\uff1b<\/p>\n

\u2461\u7edd\u5927\u591a\u6570\u7684\u919b\u916e\u5747\u53ef\u4ee5\u53c2\u52a0\u53cd\u5e94\uff0c\u4ec5\u6709\u5927\u4f4d\u963b\u7684\u916e\u4ee5\u53ca-\u4e0d\u9971\u548c\u916e\u53cd\u5e94\u6d3b\u6027\u8f83\u5dee\uff1b<\/p>\n

\u2462\u5f53\u628a\u53cd\u5e94\u7ec4\u5206\u7fa7\u9178\u6362\u6210\u6c34\u548c\u53e0\u6c2e\u9178\uff0c\u53cd\u5e94\u4ea7\u7269\u5c06\u53d8\u6210-\u7f9f\u57fa\u9170\u80fa\u548c-\u7f9f\u70f7\u57fa\u56db\u5511\u3002[2-3]<\/sup><\/p>\n

<\/a><\/p>\n

\u53cd\u5e94\u673a\u7406<\/h4>\n

Passerini\u53cd\u5e94\u7684\u673a\u7406\u6bd4\u8f83\u590d\u6742\uff0c\u4e0e\u5b9e\u9a8c\u7ed3\u679c\u8f83\u4e3a\u543b\u5408\u7684\u4e00\u79cd\u53ef\u80fd\u673a\u7406\u5982\u4e0b\u56fe\u6240\u793a\uff1a<\/p>\n

<\/a><\/p>\n

\u673a\u7406\u53ef\u5927\u81f4\u63cf\u8ff0\u4e3a\u7fb0\u57fa\u5316\u5408\u7269\u548c\u7fa7\u9178\u9996\u5148\u901a\u8fc7\u6c22\u952e\u5f62\u6210\u4e00\u4e2a\u73af\u72b6\u7edc\u5408\u7269\uff0c\u5f02\u8148\u7684\u8d1f\u78b3\u4e2d\u5fc3\u8fdb\u653b\u4eb2\u7535\u7684\u7fb0\u57fa\u78b3\u539f\u5b50\u540c\u65f6\u4e0e\u7fa7\u9178\u7684\u6c27\u539f\u5b50\u4f5c\u7528\u5f62\u6210\u4e00\u4e2a\u4e0d\u7a33\u5b9a\u7684\u4e03\u5143\u73af\u72b6\u7269\uff0c\u7136\u540e\u9170\u57fa\u53d1\u751f\u5206\u5b50\u5185\u8fc1\u79fb\u91cd\u6392\uff0c\u6700\u540e\u4e92\u53d8\u5f02\u6784\u5f97\u5230\u4ea7\u7269\u5206\u5b50\u3002[4]<\/sup><\/p>\n

 <\/p>\n

\u53cd\u5e94\u7684\u5b9e\u4f8b\u4e0e\u5e94\u7528<\/h4>\n

\u9009\u62e9\u5408\u9002\u7684\u539f\u6599\uff0c\u5229\u7528Passerini\u53cd\u5e94\u53ef\u4ee5\u5408\u6210\u591a\u79cd\u6742\u73af\u5316\u5408\u7269\u3002\u4f8b\u5982\uff0c\u9009\u62e9\u918b\u9178\u94f5\u4f5c\u4e3a\u53cd\u5e94\u7269\uff0c\u53cd\u5e94\u53ef\u4ee5\u4e0d\u505c\u7559\u5728-\u9170\u6c27\u57fa\u9170\u80fa\uff0c\u800c\u6700\u7ec8\u53ef\u4ee5\u5f97\u5230\u5641\u5511(oxazoles) [5]<\/sup>\u3002<\/p>\n

<\/a><\/p>\n

\u5f53\u6c30\u57fa\u4e59\u9178\u548c-\u7fb0\u57fa\u919b\u3001\u5f02\u8148\u4f5c\u7528\u8fd8\u53ef\u4ee5\u5f97\u52302-\u7f9f\u57fa\u544b\u5583\u884d\u751f\u7269[6]<\/sup>\u3002<\/p>\n

<\/a><\/p>\n

\u5229\u7528\u540c\u65f6\u5305\u542b\u7fb0\u57fa\u548c\u7fa7\u57fa\u7684\u53cc\u5b98\u80fd\u56e2\u5316\u5408\u7269\u4e3a\u539f\u6599\uff0c\u8fd8\u53ef\u4ee5\u5f97\u5230\u4e00\u7cfb\u5217\u4e0d\u540c\u5927\u5c0f\u73af\u7684\u5185\u916f\uff1b-\u6c2f\u4ee3\u916e\u53c2\u4e0e\u7684Passerini\u53cd\u5e94\u53ef\u4ee5\u5f97\u5230-\u5185\u9170\u80fa\uff0c\u56e0\u800c\u5177\u6709\u6781\u5927\u7684\u5e94\u7528\u524d\u666f\u2014\u2014\u4e34\u5e8a\u6700\u5e38\u7528\u7684\u9752\u9709\u7d20\u4e0e\u5934\u5b62\u83cc\u7d20\u5c31\u5c5e\u4e8e-\u5185\u9170\u80fa\u7c7b\u7684\u6297\u751f\u7d20\u3002[7]<\/sup><\/p>\n

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 <\/p>\n

\u603b\u7ed3\u4e0e\u5c55\u671b<\/strong><\/h4>\n

\u7eff\u8272\u5316\u5b66\u4e00\u76f4\u662f\u5316\u5b66\u5bb6\u4eec\u8ffd\u6c42\u7684\uff0c\u591a\u7ec4\u5206\u53cd\u5e94\u5c06\u81f3\u5c113\u4e2a\u539f\u6599\u6df7\u5408\u5728\u4e00\u4e2a\u53cd\u5e94\u74f6\u4e2d\uff0c\u5f97\u5230\u7684\u4ea7\u7269\u5f80\u5f80\u5305\u542b\u6240\u6709\u7684\u53cd\u5e94\u7269\u539f\u5b50\u3002\u591a\u7ec4\u5206\u53cd\u5e94\u517c\u6709\u539f\u5b50\u7ecf\u6d4e\u3001\u9ad8\u6548\u3001\u6e29\u548c\u4ee5\u53ca\u64cd\u4f5c\u7b80\u5355\u7684\u7279\u70b9\uff0c\u56e0\u800c\u9010\u6e10\u6210\u4e3a\u7814\u7a76\u7684\u70ed\u70b9\u3002\u5e38\u89c1\u7684\u591a\u7ec4\u5206\u53cd\u5e94\u8fd8\u5305\u62ecStrecker(1850\u5e74)\u3001Biginelli(1891\u5e74)\u3001Mannich(1912\u5e74)\u3001Ugi(1959\u5e74)\u3001Petasis(1993\u5e74)\u3001Orru(2003\u5e74)\u7b49\uff0c\u8fd9\u4e9b\u53cd\u5e94\u7684\u5e9f\u5f03\u7269\u4e00\u822c\u90fd\u662f\u6c34[8]<\/sup>\u3002\u591a\u7ec4\u5206\u53cd\u5e94\u4e0e\u8fd1\u5e74\u6765\u53d1\u5c55\u8d77\u6765\u7684\u7ec4\u5408\u5316\u5b66\u8054\u7cfb\u4ee5\u540e\uff0c\u65e0\u7591\u5c06\u5927\u5927\u6269\u5c55\u5176\u7528\u9014\u3002<\/p>\n

 <\/p>\n

\u53c2\u8003\u6587\u732e<\/h4>\n[1] Passerini,M.Gazz.Chim.Ital.<\/em>1921<\/strong>,51,181-189.<\/p>\n[2](a)Baker,R.H.,Schlesinger,A.H.J.Am.Chem.Soc<\/em>.1945<\/strong>,67,1499-1500. doi:10.1021\/ja01225a027 (b)Mueller,E.,Zeeh,B.Liebigs Ann.Chem<\/em>.1966<\/strong>,696,72-80.doi:10.1002\/jlac.19666960108<\/p>\n[3](a)Passerini,M.Gazz.Chim.Ital.<\/em>1922<\/strong>,52,432-435.<\/p>\n

(b)McFarland,J.W.J.Org.Chem.<\/em>1963<\/strong>,28,2179-2181.doi:10.1021\/jo01044a006<\/p>\n[4]L\u00e1szl\u00f3K\u00fcrti and Barbara Czak\u00f3StrategicApplications Of Named<\/em> Reactions In Organic Synthesis<\/em>, Elsevier Press,\u00a02005,<\/strong>pp330-331.<\/p>\n[5] Bossio,R., Marcaccini,S., Pepino,R.Liebigs Ann.Chem<\/em>.1991<\/strong>,1107-1108.doi:10.1002\/jlac.1991199101193<\/p>\n[6] Bossio,R., Marcaccini,S., Pepino,R., Torroba,T.Synthesis<\/em>1993<\/strong>,783-785.doi:10.1055\/s-1993-25940<\/p>\n[7]Sebti,S., Foucaud,A.Synthesis<\/em>.1983<\/strong>,546-549.doi:10.1055\/s-1983-30418<\/p>\n[8] R\u0103zvan C. Cioc, EelcoRuijter and Romano V. A. Orru.Green Chem<\/em>., 2014<\/strong>, 16,2958-2975.doi:10.1039\/C4GC00013G<\/p>\n

 <\/p>\n

\u672c\u6587\u7248\u6743\u5c5e\u4e8e\u00a0Chem-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","protected":false},"excerpt":{"rendered":"\u6982\u8ff0 \u5f02\u8148\u662f\u4e00\u7c7b\u72ec\u7279\u7684\u6709\u673a\u7269\uff0c\u53ef\u4ee5\u540c\u65f6\u4e0e\u4eb2\u7535\u8bd5\u5242\u3001\u4eb2\u6838\u8bd5\u5242\u53cd\u5e94\u3002\u5f02\u8148\u5728\u5408\u6210\u4e0a\u6709\u7528\u9014\u7684\u7b2c\u4e00\u4e2a\u53cd\u5e94\u662f\u7531M.Passerini\u62a5\u9053\u7684\uff0c\u4ed6\u63d0\u51fa\u5f02\u8148\u548c\u7fa7\u9178\u8fd8\u6709\u7fb0\u57fa\u5316\u5408\u7269(\u919b\u6216\u916e)\u4e00\u6b65\u53cd\u5e94\u53ef\u5f97\u5230-\u9170\u6c27\u57fa\u9170\u80fa\uff0c\u4e5f\u5c31\u662f\u73b0\u5728\u6240\u719f\u77e5\u7684Passerini multicomponent reaction(MCR)\u3002[1] \u7279\u70b9 Passerini\u53cd\u5e94\u5177\u6709\u5982\u4e0b\u51e0\u4e2a\u7279\u5f81\uff1a \u2460\u539f\u5b50\u5229\u7528\u7387\u9ad8\uff0c\u60f0\u6027\u975e\u6781\u6027\u6eb6\u5242\u6709\u5229\u4e8e\u53cd\u5e94\uff1b \u2461\u7edd\u5927\u591a\u6570\u7684\u919b\u916e\u5747\u53ef\u4ee5\u53c2\u52a0\u53cd\u5e94\uff0c\u4ec5\u6709\u5927\u4f4d\u963b\u7684\u916e\u4ee5\u53ca-\u4e0d\u9971\u548c\u916e\u53cd\u5e94\u6d3b\u6027\u8f83\u5dee\uff1b \u2462\u5f53\u628a\u53cd\u5e94\u7ec4\u5206\u7fa7\u9178\u6362\u6210\u6c34\u548c\u53e0\u6c2e\u9178\uff0c\u53cd\u5e94\u4ea7\u7269\u5c06\u53d8\u6210-\u7f9f\u57fa\u9170\u80fa\u548c-\u7f9f\u70f7\u57fa\u56db\u5511\u3002[2-3] \u53cd\u5e94\u673a\u7406 Passerini\u53cd\u5e94\u7684\u673a\u7406\u6bd4\u8f83\u590d\u6742\uff0c\u4e0e\u5b9e\u9a8c\u7ed3\u679c\u8f83\u4e3a\u543b\u5408\u7684\u4e00\u79cd\u53ef\u80fd\u673a\u7406\u5982\u4e0b\u56fe\u6240\u793a\uff1a \u673a\u7406\u53ef\u5927\u81f4\u63cf\u8ff0\u4e3a\u7fb0\u57fa\u5316\u5408\u7269\u548c\u7fa7\u9178\u9996\u5148\u901a\u8fc7\u6c22\u952e\u5f62\u6210\u4e00\u4e2a\u73af\u72b6\u7edc\u5408\u7269\uff0c\u5f02\u8148\u7684\u8d1f\u78b3\u4e2d\u5fc3\u8fdb\u653b\u4eb2\u7535\u7684\u7fb0\u57fa\u78b3\u539f\u5b50\u540c\u65f6\u4e0e\u7fa7\u9178\u7684\u6c27\u539f\u5b50\u4f5c\u7528\u5f62\u6210\u4e00\u4e2a\u4e0d\u7a33\u5b9a\u7684\u4e03\u5143\u73af\u72b6\u7269\uff0c\u7136\u540e\u9170\u57fa\u53d1\u751f\u5206\u5b50\u5185\u8fc1\u79fb\u91cd\u6392\uff0c\u6700\u540e\u4e92\u53d8\u5f02\u6784\u5f97\u5230\u4ea7\u7269\u5206\u5b50\u3002[4]   \u53cd\u5e94\u7684\u5b9e\u4f8b\u4e0e\u5e94\u7528 \u9009\u62e9\u5408\u9002\u7684\u539f\u6599\uff0c\u5229\u7528Passerini\u53cd\u5e94\u53ef\u4ee5\u5408\u6210\u591a\u79cd\u6742\u73af\u5316\u5408\u7269\u3002\u4f8b\u5982\uff0c\u9009\u62e9\u918b\u9178\u94f5\u4f5c\u4e3a\u53cd\u5e94\u7269\uff0c\u53cd\u5e94\u53ef\u4ee5\u4e0d\u505c\u7559\u5728-\u9170\u6c27\u57fa\u9170\u80fa\uff0c\u800c\u6700\u7ec8\u53ef\u4ee5\u5f97\u5230\u5641\u5511(oxazoles) [5]\u3002 \u5f53\u6c30\u57fa\u4e59\u9178\u548c-\u7fb0\u57fa\u919b\u3001\u5f02\u8148\u4f5c\u7528\u8fd8\u53ef\u4ee5\u5f97\u52302-\u7f9f\u57fa\u544b\u5583\u884d\u751f\u7269[6]\u3002 \u5229\u7528\u540c\u65f6\u5305\u542b\u7fb0\u57fa\u548c\u7fa7\u57fa\u7684\u53cc\u5b98\u80fd\u56e2\u5316\u5408\u7269\u4e3a\u539f\u6599\uff0c\u8fd8\u53ef\u4ee5\u5f97\u5230\u4e00\u7cfb\u5217\u4e0d\u540c\u5927\u5c0f\u73af\u7684\u5185\u916f\uff1b-\u6c2f\u4ee3\u916e\u53c2\u4e0e\u7684Passerini\u53cd\u5e94\u53ef\u4ee5\u5f97\u5230-\u5185\u9170\u80fa\uff0c\u56e0\u800c\u5177\u6709\u6781\u5927\u7684\u5e94\u7528\u524d\u666f\u2014\u2014\u4e34\u5e8a\u6700\u5e38\u7528\u7684\u9752\u9709\u7d20\u4e0e\u5934\u5b62\u83cc\u7d20\u5c31\u5c5e\u4e8e-\u5185\u9170\u80fa\u7c7b\u7684\u6297\u751f\u7d20\u3002[7]   \u603b\u7ed3\u4e0e\u5c55\u671b \u7eff\u8272\u5316\u5b66\u4e00\u76f4\u662f\u5316\u5b66\u5bb6\u4eec\u8ffd\u6c42\u7684\uff0c\u591a\u7ec4\u5206\u53cd\u5e94\u5c06\u81f3\u5c113\u4e2a\u539f\u6599\u6df7\u5408\u5728\u4e00\u4e2a\u53cd\u5e94\u74f6\u4e2d\uff0c\u5f97\u5230\u7684\u4ea7\u7269\u5f80\u5f80\u5305\u542b\u6240\u6709\u7684\u53cd\u5e94\u7269\u539f\u5b50\u3002\u591a\u7ec4\u5206\u53cd\u5e94\u517c\u6709\u539f\u5b50\u7ecf\u6d4e\u3001\u9ad8\u6548\u3001\u6e29\u548c\u4ee5\u53ca\u64cd\u4f5c\u7b80\u5355\u7684\u7279\u70b9\uff0c\u56e0\u800c\u9010\u6e10\u6210\u4e3a\u7814\u7a76\u7684\u70ed\u70b9\u3002\u5e38\u89c1\u7684\u591a\u7ec4\u5206\u53cd\u5e94\u8fd8\u5305\u62ecStrecker(1850\u5e74)\u3001Biginelli(1891\u5e74)\u3001Mannich(1912\u5e74)\u3001Ugi(1959\u5e74)\u3001Petasis(1993\u5e74)\u3001Orru(2003\u5e74)\u7b49\uff0c\u8fd9\u4e9b\u53cd\u5e94\u7684\u5e9f\u5f03\u7269\u4e00\u822c\u90fd\u662f\u6c34[8]\u3002\u591a\u7ec4\u5206\u53cd\u5e94\u4e0e\u8fd1\u5e74\u6765\u53d1\u5c55\u8d77\u6765\u7684\u7ec4\u5408\u5316\u5b66\u8054\u7cfb\u4ee5\u540e\uff0c\u65e0\u7591\u5c06\u5927\u5927\u6269\u5c55\u5176\u7528\u9014\u3002   \u53c2\u8003\u6587\u732e [1] Passerini,M.Gazz.Chim.Ital.1921,51,181-189. [2](a)Baker,R.H.,Schlesinger,A.H.J.Am.Chem.Soc.1945,67,1499-1500. doi:10.1021\/ja01225a027 (b)Mueller,E.,Zeeh,B.Liebigs Ann.Chem.1966,696,72-80.doi:10.1002\/jlac.19666960108 [3](a)Passerini,M.Gazz.Chim.Ital.1922,52,432-435. (b)McFarland,J.W.J.Org.Chem.1963,28,2179-2181.doi:10.1021\/jo01044a006 [4]L\u00e1szl\u00f3K\u00fcrti and Barbara Czak\u00f3StrategicApplications Of Named Reactions In Organic Synthesis, Elsevier Press,\u00a02005,pp330-331. [5] Bossio,R., Marcaccini,S., Pepino,R.Liebigs Ann.Chem.1991,1107-1108.doi:10.1002\/jlac.1991199101193 [6] Bossio,R., Marcaccini,S., Pepino,R., Torroba,T.Synthesis1993,783-785.doi:10.1055\/s-1993-25940 [7]Sebti,S., Foucaud,A.Synthesis.1983,546-549.doi:10.1055\/s-1983-30418 [8] R\u0103zvan C. Cioc, EelcoRuijter and Romano V. A. 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