{"id":24517,"date":"2019-02-13T11:32:26","date_gmt":"2019-02-13T03:32:26","guid":{"rendered":"\/\/www.gsbet888.com\/?p=24517"},"modified":"2019-02-13T11:32:26","modified_gmt":"2019-02-13T03:32:26","slug":"j-am-chem-soc-%e8%ae%a1%e7%ae%97%e5%8c%96%e5%ad%a6%e8%be%85%e5%8a%a9%e5%a4%a9%e7%84%b6%e4%ba%a7%e7%89%a9%e5%85%a8%e5%90%88%e6%88%90","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/%e5%8c%96%e5%ad%a6%e6%9d%82%e8%ae%b0\/2019\/02\/j-am-chem-soc-%e8%ae%a1%e7%ae%97%e5%8c%96%e5%ad%a6%e8%be%85%e5%8a%a9%e5%a4%a9%e7%84%b6%e4%ba%a7%e7%89%a9%e5%85%a8%e5%90%88%e6%88%90.html","title":{"rendered":"J. Am. Chem. Soc. \u8ba1\u7b97\u5316\u5b66\u8f85\u52a9\u5929\u7136\u4ea7\u7269\u5168\u5408\u6210"},"content":{"rendered":"

\u8fd9\u6b21\u4ecb\u7ecd\u7684\u8bba\u6587\u62a5\u9053\u4e86\u7b80\u77ed\u8def\u7ebf\u7684Paspaline A\u7684\u5168\u5408\u6210<\/b>\u3001\u4ee5\u53caEmindole PB\u7684\u9996\u6b21\u5168\u5408\u6210<\/strong><\/b>\u3002\u901a\u8fc7\u4f7f\u7528DFT\u8ba1\u7b97\uff0c\u9ad8\u6548\u786e\u5b9a\u4e86\u4e2d\u95f4\u4f53\u7684\u6700\u4f73\u7ed3\u6784\uff0c\u51cf\u5c11\u4e86\u4e0d\u5fc5\u8981\u7684\u5c1d\u8bd5\uff0c\u8282\u7ea6\u4e86\u65f6\u95f4\u3002<\/b><\/b><\/p>\n

\u7528\u8ba1\u7b97\u5316\u5b66\u8bc4\u4ef7\u53cd\u5e94\u7684\u53ef\u884c\u6027\u53ca\u5176\u5728\u5929\u7136\u4ea7\u7269\u5408\u6210\u4e2d\u7684\u5e94\u7528<\/h4>\n

\u9006\u5408\u6210\u5206\u6790\u6cd5\u662f\u5728\u5316\u5408\u7269\u7684\u5408\u6210\u8def\u7ebf\u8bbe\u8ba1\u4e2d\u6700\u5e38\u7528\u7684\u4e00\u79cd\u7406\u8bba\u65b9\u6cd5\u3002\u4f46\u662f\uff0c\u5bf9\u4e8e\u7b80\u5316\u5408\u6210\u7684\u9006\u5408\u6210\u5206\u6790\u65ad\u952e\u6cd5\u6765\u8bf4\uff0c\u7531\u4e8e\u53ef\u53c2\u8003\u7684\u6587\u732e\u662f\u4e0d\u5145\u8db3\u7684\uff0c\u6240\u4ee5\u5f88\u591a\u8fd8\u9700\u8981\u901a\u8fc7\u5b9e\u9645\u7684\u5b9e\u9a8c\u9a8c\u8bc1\u5176\u53ef\u884c\u6027\u3002\u73b0\u4ee3\u7684\u7535\u8111\u8ba1\u7b97\uff0c\u9010\u6e10\u8f6c\u53d8\u6210\u8fd9\u79cd\u9006\u5408\u6210\u5206\u6790\u7684\u5f3a\u529b\u7684\u624b\u6bb5\u4e4b\u4e00\u3002\u6362\u53e5\u8bdd\u8bf4\uff0c\u901a\u8fc7\u7b97\u6cd5\u7684\u5f00\u53d1\u53ef\u4ee5\u6709\u6548\u5730\u8bc6\u522b\u5316\u5b66\u952e\u65ad\u88c2\u4e0e\u901a\u8fc7\u91cf\u5b50\u5316\u5b66\u8ba1\u7b97\u5b9e\u73b0\u524d\u6240\u672a\u6709\u7684\u5408\u6210\u8def\u7ebf\u7684\u8bbe\u8ba1\u6210\u4e3a\u53ef\u80fd\u3002<\/p>\n

\u53e6\u4e00\u65b9\u9762\uff0c\u5432\u54da\u4e8c\u841c\u7c7b\u5316\u5408\u7269\u4e00\u76f4\u662f\u4f5c\u4e3a\u5168\u5408\u6210\u7814\u7a76\u76ee\u6807\u7684\u5929\u7136\u4ea7\u7269\u7fa4\u3002Paspaline A\uff081\uff09<\/strong>\u5177\u6709\u516d\u73af\u9aa8\u67b6\uff0c\u4e14\u542b\u6709\u4e0e\u8fde\u7eed\u5b63\u78b3\u76f8\u90bb\u7684\u5432\u54da\u7a20\u5408\u73af\u620a\u70f7\u7ed3\u6784\u3002\u8be5\u7c7b\u5929\u7136\u4ea7\u7269\u5177\u6709\u6297\u54fa\u4e73\u52a8\u7269\u4e73\u817a\u764c\u7684\u6297\u589e\u6b96\u30fb\u6297\u8f6c\u79fb\u6d3b\u6027\u3002\u5728\u8fc4\u4eca\u5df2\u62a5\u9053\u76841\u7684\u5168\u5408\u6210\u4e2d\uff0c\u91c7\u7528\u4e86\u5432\u54da\u73af\u4e0eD\u73af\u4e4b\u95f4\u7684\u73af\u620a\u916e\u90e8\u5206\uff08C\u73af\uff09\u7684\u6784\u5efa\u7684\u5408\u6210\u7b56\u7565\u3001\u5408\u6210\u6b65\u9aa4\u591a(\u56fe<\/span>1A)[2,3]<\/sup><\/span>\u3002\u53e6\u5916\u3001Emindole\u00a0PB (2<\/b>)\u7684\u5168\u5408\u6210\u8fd8\u672a\u6709\u62a5\u9053<\/span>\u3002<\/p>\n

\u8fd9\u6b21\u3001\u8036\u9c81\u5927\u5b66\u7684Newhouse\u526f<\/span>\u6559\u6388\u8bfe\u9898\u7ec4\u3001\u6a21\u4eff\u751f\u7269\u5408\u6210\u7684\u5408\u6210\u7b56\u7565\uff08\u56fe1C\uff09\u3001\u901a\u8fc7\u4f7f\u7528\u5432\u54da\u7684\u4eb2\u6838\u6027\u6765\u6784\u5efaC\u73af\uff0c\u5b9e\u73b0\u4e86\u77ed\u7a0b\u5168\u5408\u6210\u3002\u6b64\u5916\uff0c\u901a\u8fc7\u5bf9\u76f8\u540c\u7684\u4e2d\u95f4\u4f53\u8fdb\u884c\u7532\u57fa\u91cd\u6392\uff0c\u6210\u529f\u5b9e\u73b0\u4e86\u9996\u6b21Emindole\u00a0<\/strong>PB<\/strong> (2<\/b>)\u7684<\/span>\u5168\u5408\u6210\u548c\u7ed3\u6784\u6d4b\u5b9a\uff08\u56fe1B\uff09\u3002\u901a\u8fc7\u4f7f\u7528\u5bc6\u5ea6\u6cdb\u51fd\u7406\u8bba\uff08DFT\uff09\u8ba1\u7b97\u786e\u5b9aC\u73af\u7684\u73af\u5316\u524d\u4f53\u7684\u6700\u4f73\u7ed3\u6784\uff0c\u6210\u529f\u5730\u964d\u4f4e\u4e86\u6700\u4f18\u5316\u5408\u6210\u8def\u7ebf\u7684\u7b5b\u9009\u4e0a\u7684\u8017\u65f6\u3002<\/p>\n

\n

\"\"<\/p>\n

\u56fe1. (A) Paspaline A\u7684\u5168\u5408\u6210\u62a5\u9053 (B) \u8fd9\u6b21\u7684\u5408\u6210\u7b56\u7565 (C) \u751f\u7269\u5408\u6210<\/p>\n<\/div>\n

 <\/p>\n

\u201c<\/strong>Total Synthesis of Paspaline A and Emindole PB Enabled by Computational <\/strong>Augmentation of a Transform-Guided Retrosynthetic Strategy<\/strong>\u201d<\/strong><\/p>\n

Kim, D. E.; Zweig, J. E.; Newhouse, T. R. J. Am. Chem. Soc.<\/em>2019<\/strong>, ASAP.\u00a0DOI: 10.1021\/jacs.8b13127<\/a><\/p><\/blockquote>\n

\u8bba\u6587\u4f5c\u8005\u4ecb\u7ecd<\/h4>\n

\"\"<\/p>\n

Timothy R. Newhouse<\/strong><\/a><\/p>\n

\u5c65\u5386\uff1a
\n2001-2005 B.A., Colby College, ME, USA (Prof. Dasan M. Thamattoor)
\n2006-2010 Ph.D, The Scripps Research Institute, CA, USA (Prof. Phil S. Baran<\/a> and Prof. Donna G. Blackmond)
\n2010-2013 Posdoc,Harvard University, MA, USA (Prof. E. J. Corey<\/a>)
\n2013-2018 Assistant Prof. at Yale University, CT, USA
\n2018- Associate Prof. at Yale University<\/p>\n

\u7814\u7a76\u5185\u5bb9\uff1a\u8ba1\u7b97\u5316\u5b66\u8f85\u52a9\u5929\u7136\u4ea7\u7269\u5168\u5408\u6210\u3001\u8fc7\u6e21\u91d1\u5c5e\u50ac\u5316\u7684\u53cd\u5e94\u65b9\u6cd5\u5b66\u5f00\u53d1\u53ca\u5168\u5408\u6210<\/p>\n

\u8bba\u6587\u6982\u8981<\/h4>\n

\u3000Newhouse\u526f<\/span>\u6559\u6388\u7b49\u4eba\u3001\u9996\u5148\u5c06\u5432\u54da\u4e0e\u4e8c\u841c\u9aa8\u67b6\u8fde\u63a5\uff0c\u5e76\u8ba1\u5212\u4f7f\u7528\u5432\u54da\u7684\u4eb2\u6838\u6027\u901a\u8fc7C\u73af\u6784\u5efa\u6765\u5b9e\u73b01<\/span><\/b>\u7684\u5408\u6210\u3002\u901a\u8fc7\u5bf9\u4f4d\u4e8e\u8fdc\u7aef\u4f4d\u7684\u5177\u6709\u4e0d\u540cF\u73af\u524d\u4f53\u7ed3\u6784\u7684\u4e09\u79cd\u5316\u5408\u7269\u7684\u4e09\u7ea7\u78b3\u6b63\u79bb\u5b50\u4e2d\u95f4\u4f53Z(a)<\/span><\/b>\u2013Z(c)<\/b><\/span>\u8fdb\u884cDFT\u8ba1\u7b97\u6765\u6bd4\u8f83\u5b83\u4eec\u7684\u53cd\u5e94\u9009\u62e9\u6027\uff0c\u6765\u9884\u6d4b\u6700\u5bb9\u6613\u73af\u5316\u7684\u5e95\u7269\u7ed3\u6784(\u56fe<\/span>2A)<\/span>\u3002\u5177\u4f53\u800c\u8a00\uff0c\u662f\u8ba1\u7b97\u4e86\u4e09\u7ea7\u78b3\u6b63\u79bb\u5b50\u4e2d\u95f4\u4f53\u73af\u5316\u4e0e\u7532\u57fa\u91cd\u6392\u53cd\u5e94\u8fdb\u884c\u65f6\u7684\u80fd\u91cf\u58c1\u5792\u7684\u5dee\u3002\u7ed3\u679c\u53d1\u73b0\uff0c\u5f53\u4f7f\u7528\u5728F\u73af\u4e0a\u5177\u6709\u53cc\u73af\u7f29\u916e\u7ed3\u6784Z(c)<\/span><\/b>\u65f6\uff0c\u7532\u57fa\u91cd\u6392\u4e0e\u73af\u5316\u7684\u80fd\u5792\u4e4b\u95f4\u7684\u5dee\u6700\u5927\uff08-4.5kcal \/ mol\uff09,\u56e0\u6b64\u4f5c\u8005\u51b3\u5b9a\u901a\u8fc7\u7ecf\u7531\u8be5\u4e2d\u95f4\u4f53\u5408\u62101<\/span><\/b>\u3002<\/p>\n

\u3000\u4f5c\u8005\u4eceWieland-Miescher \u916e\u884d\u751f\u7269\u51fa\u53d1\uff0c5\u6b65\u5408\u6210\u4e86\u73af\u5316\u524d\u4f53<\/span>3<\/span><\/b>\u3001\u7136\u540e\u5728AlCl3<\/sub><\/span>\u4f5c\u7528\u4e0b\u3001\u5f97\u5230\u4e86C\u73af\u73af\u5316\u4f534<\/span><\/b>\u4e0e\u7532\u57fa\u91cd\u6392\u4f535<\/span><\/b>(4<\/b>:5<\/b>= 1:3)(\u56fe<\/span>2B)<\/span>\u30024<\/span><\/b>\u5728\u8fd8\u539f\u6761\u4ef6\u4e0b\u8bf1\u5bfc\u5408\u6210\u4e86Paspaline A<\/strong>(1<\/b>)<\/span>(\u5408\u8ba1<\/span>9\u6b65\u53cd\u5e94<\/span>)<\/span>\u3002\u53e6\u4e00\u65b9\u9762\u3001\u4ece5<\/strong>\u5f00\u59cb\uff0c\u52064\u6b65\u8fdb\u884c\u70ef\u70c3\u7684\u5f02\u6784\u5316\u548cF\u73af\u7684\u5f62\u6210\uff0c\u6700\u540e\uff0c\u5c06\u6c2e\u539f\u5b50\u53d4\u4e01\u57fa\u5316\uff0c\u5f97\u5230Emindole\u00a0<\/strong>PB<\/strong> (2<\/b>)<\/span>\uff08\u517114\u6b65\uff09\u3002<\/p>\n

\n

\"\"<\/p>\n

\u56fe2. (A)DFT\u8ba1\u7b97 (B)Paspaline A\u4ee5\u53caEmindole PB\u7684\u5408\u6210<\/p>\n<\/div>\n

\u7efc\u4e0a\u3001\u672c\u6b21\u4f5c\u8005\u4ee51\/3\u7684\u6b65\u9aa4\u6570\u5408\u6210\u4e86Paspaline A<\/strong>\u4e0eEmindole PB<\/strong>\u3002\u901a\u8fc7DFT\u8ba1\u7b97\u786e\u5b9a\u4e86\u6700\u4f18\u5e95\u7269\uff0c\u8282\u7701\u4e86\u65f6\u95f4<\/span>\u3002\u5c3d\u7ba1\u8fd9\u79cd\u8ba1\u7b97\u65b9\u6cd5\u7684\u80fd\u529b\u548c\u5c40\u9650\u6027\u662f\u672a\u77e5\u7684\u4f46\u975e\u5e38\u671f\u5f85\u901a\u8fc7\u672a\u6765\u7814\u7a76\u7684\u8fdb\u4e00\u6b65\u53d1\u5c55\uff0c\u4f7f\u5f97\u8fd9\u79cd\u65b9\u6cd5\u53d8\u5f97\u66f4\u53ef\u9760\u3002<\/p>\n

\u53c2\u8003\u6587\u732e<\/h4>\n
    \n
  1. Corey, E. J.; Wipke, W. T. Science <\/em>1969<\/strong>, 166<\/em>, 178\u2013192.DOI: 1126\/science.166.3902.178 <\/a><\/li>\n
  2. (a) Smith, A. B.; Mewshaw, R. J.<\/em>\u00a0Am. Chem. Soc. <\/em>1985<\/strong>, 107<\/em>, 1769\u20131771. DOI: 10.1021\/ja00292a058<\/a> (b) Smith, A. B.; Leenay, T. L. J. Am. Chem. Soc. <\/em>1989<\/strong>, 111<\/em>, 5761\u20135768. DOI: 10.1021\/ja00197a039<\/a><\/li>\n
  3. Sharpe, R. J.; Johnson, J. S. J.\u00a0Am. Chem. Soc. <\/em>2015<\/strong>, 137<\/em>, 4968\u20134971. DOI: 10.1021\/jacs.5b02631<\/a><\/li>\n<\/ol>\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":"\u8fd9\u6b21\u4ecb\u7ecd\u7684\u8bba\u6587\u62a5\u9053\u4e86\u7b80\u77ed\u8def\u7ebf\u7684Paspaline A\u7684\u5168\u5408\u6210\u3001\u4ee5\u53caEmindole PB\u7684\u9996\u6b21\u5168\u5408\u6210\u3002\u901a\u8fc7\u4f7f\u7528DFT\u8ba1\u7b97\uff0c\u9ad8\u6548\u786e\u5b9a\u4e86\u4e2d\u95f4\u4f53\u7684\u6700\u4f73\u7ed3\u6784\uff0c\u51cf\u5c11\u4e86\u4e0d\u5fc5\u8981\u7684\u5c1d\u8bd5\uff0c\u8282\u7ea6\u4e86\u65f6\u95f4\u3002 \u7528\u8ba1\u7b97\u5316\u5b66\u8bc4\u4ef7\u53cd\u5e94\u7684\u53ef\u884c\u6027\u53ca\u5176\u5728\u5929\u7136\u4ea7\u7269\u5408\u6210\u4e2d\u7684\u5e94\u7528 \u9006\u5408\u6210\u5206\u6790\u6cd5\u662f\u5728\u5316\u5408\u7269\u7684\u5408\u6210\u8def\u7ebf\u8bbe\u8ba1\u4e2d\u6700\u5e38\u7528\u7684\u4e00\u79cd\u7406\u8bba\u65b9\u6cd5\u3002\u4f46\u662f\uff0c\u5bf9\u4e8e\u7b80\u5316\u5408\u6210\u7684\u9006\u5408\u6210\u5206\u6790\u65ad\u952e\u6cd5\u6765\u8bf4\uff0c\u7531\u4e8e\u53ef\u53c2\u8003\u7684\u6587\u732e\u662f\u4e0d\u5145\u8db3\u7684\uff0c\u6240\u4ee5\u5f88\u591a\u8fd8\u9700\u8981\u901a\u8fc7\u5b9e\u9645\u7684\u5b9e\u9a8c\u9a8c\u8bc1\u5176\u53ef\u884c\u6027\u3002\u73b0\u4ee3\u7684\u7535\u8111\u8ba1\u7b97\uff0c\u9010\u6e10\u8f6c\u53d8\u6210\u8fd9\u79cd\u9006\u5408\u6210\u5206\u6790\u7684\u5f3a\u529b\u7684\u624b\u6bb5\u4e4b\u4e00\u3002\u6362\u53e5\u8bdd\u8bf4\uff0c\u901a\u8fc7\u7b97\u6cd5\u7684\u5f00\u53d1\u53ef\u4ee5\u6709\u6548\u5730\u8bc6\u522b\u5316\u5b66\u952e\u65ad\u88c2\u4e0e\u901a\u8fc7\u91cf\u5b50\u5316\u5b66\u8ba1\u7b97\u5b9e\u73b0\u524d\u6240\u672a\u6709\u7684\u5408\u6210\u8def\u7ebf\u7684\u8bbe\u8ba1\u6210\u4e3a\u53ef\u80fd\u3002 \u53e6\u4e00\u65b9\u9762\uff0c\u5432\u54da\u4e8c\u841c\u7c7b\u5316\u5408\u7269\u4e00\u76f4\u662f\u4f5c\u4e3a\u5168\u5408\u6210\u7814\u7a76\u76ee\u6807\u7684\u5929\u7136\u4ea7\u7269\u7fa4\u3002Paspaline A\uff081\uff09\u5177\u6709\u516d\u73af\u9aa8\u67b6\uff0c\u4e14\u542b\u6709\u4e0e\u8fde\u7eed\u5b63\u78b3\u76f8\u90bb\u7684\u5432\u54da\u7a20\u5408\u73af\u620a\u70f7\u7ed3\u6784\u3002\u8be5\u7c7b\u5929\u7136\u4ea7\u7269\u5177\u6709\u6297\u54fa\u4e73\u52a8\u7269\u4e73\u817a\u764c\u7684\u6297\u589e\u6b96\u30fb\u6297\u8f6c\u79fb\u6d3b\u6027\u3002\u5728\u8fc4\u4eca\u5df2\u62a5\u9053\u76841\u7684\u5168\u5408\u6210\u4e2d\uff0c\u91c7\u7528\u4e86\u5432\u54da\u73af\u4e0eD\u73af\u4e4b\u95f4\u7684\u73af\u620a\u916e\u90e8\u5206\uff08C\u73af\uff09\u7684\u6784\u5efa\u7684\u5408\u6210\u7b56\u7565\u3001\u5408\u6210\u6b65\u9aa4\u591a(\u56fe1A)[2,3]\u3002\u53e6\u5916\u3001Emindole\u00a0PB (2)\u7684\u5168\u5408\u6210\u8fd8\u672a\u6709\u62a5\u9053\u3002 \u8fd9\u6b21\u3001\u8036\u9c81\u5927\u5b66\u7684Newhouse\u526f\u6559\u6388\u8bfe\u9898\u7ec4\u3001\u6a21\u4eff\u751f\u7269\u5408\u6210\u7684\u5408\u6210\u7b56\u7565\uff08\u56fe1C\uff09\u3001\u901a\u8fc7\u4f7f\u7528\u5432\u54da\u7684\u4eb2\u6838\u6027\u6765\u6784\u5efaC\u73af\uff0c\u5b9e\u73b0\u4e86\u77ed\u7a0b\u5168\u5408\u6210\u3002\u6b64\u5916\uff0c\u901a\u8fc7\u5bf9\u76f8\u540c\u7684\u4e2d\u95f4\u4f53\u8fdb\u884c\u7532\u57fa\u91cd\u6392\uff0c\u6210\u529f\u5b9e\u73b0\u4e86\u9996\u6b21Emindole\u00a0PB (2)\u7684\u5168\u5408\u6210\u548c\u7ed3\u6784\u6d4b\u5b9a\uff08\u56fe1B\uff09\u3002\u901a\u8fc7\u4f7f\u7528\u5bc6\u5ea6\u6cdb\u51fd\u7406\u8bba\uff08DFT\uff09\u8ba1\u7b97\u786e\u5b9aC\u73af\u7684\u73af\u5316\u524d\u4f53\u7684\u6700\u4f73\u7ed3\u6784\uff0c\u6210\u529f\u5730\u964d\u4f4e\u4e86\u6700\u4f18\u5316\u5408\u6210\u8def\u7ebf\u7684\u7b5b\u9009\u4e0a\u7684\u8017\u65f6\u3002 \u56fe1. 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