{"id":194,"date":"2014-01-10T11:39:14","date_gmt":"2014-01-10T03:39:14","guid":{"rendered":"\/\/www.gsbet888.com\/?p=194"},"modified":"2019-08-02T18:57:21","modified_gmt":"2019-08-02T10:57:21","slug":"%e6%88%b4%e6%96%af%ef%bc%8d%e9%a9%ac%e4%b8%81%e6%b0%a7%e5%8c%96%e5%89%82%ef%bc%88dess-martin-oxidation%ef%bc%89","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/2014\/01\/%e6%88%b4%e6%96%af%ef%bc%8d%e9%a9%ac%e4%b8%81%e6%b0%a7%e5%8c%96%e5%89%82%ef%bc%88dess-martin-oxidation%ef%bc%89.html","title":{"rendered":"\u6234\u65af\uff0d\u9a6c\u4e01\u6c27\u5316\u5242\uff08Dess-Martin Oxidation\uff09"},"content":{"rendered":"<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u00a0\u6982\u8981<\/strong><\/li>\n<\/ul>\n<p align=\"left\">\u6234\u65af\uff0d\u9a6c\u4e01\u6c27\u5316\u5242<b>Dess-Martin periodinane (DMP)<\/b>\u53ef\u4ee5\u6c27\u5316\u9187\u5316\u5408\u7269\u3002<\/p>\n<p align=\"left\">\u53cd\u5e94\u5728\u5ba4\u6e29\u5feb\u901f\u8fdb\u884c\uff0c\u53ef\u4ee5\u5c06\u4f2f\u9187\u6c27\u5316\u6210\u919b\u3002\u5bf9\u8f83\u5927\u4f4d\u963b\u7684\u9187\u3001\u53ca\u5728\u03b1\u4f4d\u6709\u4e0d\u5bf9\u79f0\u4e2d\u5fc3\u7684\u5916\u6d88\u65cb\u6df7\u5408\u7269\uff08\u6bd4\u5982\u7fb0\u57fa\u5316\u5408\u7269\uff09\u3001\u6216\u03b1,\u03b2-\u4e0d\u9971\u548c\u919b\u7684\u5408\u6210\u975e\u5e38\u6709\u6548\u3002\u6240\u4ee5\u672c\u53cd\u5e94\u88ab\u5e94\u7528\u5728\u591a\u79cd\u590d\u6742\u5316\u5408\u7269\u7684\u5408\u6210\u4e2d\u3002<\/p>\n<p align=\"left\">\u672c\u53cd\u5e94\u80fd\u7528\u4e8e\u8bb8\u591a\u5bf9\u9178\u30fb\u78b1\u4e0d\u7a33\u5b9a\u7684\u5e95\u7269\u3002\u4ece\u53cd\u5e94\u673a\u7406\u6765\u8bf4\u4f1a\u4ea7\u751f\uff082\u5f53\u91cf\uff09\u4ee5\u4e0a\u7684\u918b\u9178\uff0c\u5373\u4f7f\u5e95\u7269\u5bf9\u751f\u6210\u7684\u918b\u9178\u4e0d\u7a33\u5b9a\u3001\u53ef\u7528\u5421\u5576\u7b49\u5f53\u7f13\u51b2\u5242\u907f\u514d\u8fd9\u4e00\u95ee\u9898\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u57fa\u672c\u6587\u732e<\/strong><\/li>\n<\/ul>\n<p>\u30fbDess, D. B.; Martin, J. C.\u00a0<em>J. Org. Chem.<\/em>\u00a0<strong>1983<\/strong>,\u00a0<em>48<\/em>, 4155. DOI:<a href=\"http:\/\/dx.doi.org\/10.1021\/jo00170a070\">\u00a010.1021\/jo00170a070<\/a><br \/>\n\u30fbDess, D. B.; Matrin, J. C.\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong>1991<\/strong>,\u00a0<em>113<\/em>, 7277. doi:<a href=\"http:\/\/dx.doi.org\/10.1021\/ja00019a027\">10.1021\/ja00019a027<\/a><br \/>\n\u30fbStevenson, P. J.; Treacy, A. B.\u00a0<em>J. C. S. Perkin Trans. 2<\/em>\u00a0<strong>1997<\/strong>, 589. DOI:\u00a0<a href=\"http:\/\/dx.doi.org\/10.1039\/a605253c\">10.1039\/a605253c<\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u673a\u7406<\/strong><\/li>\n<\/ul>\n<p><strong><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/ol-al-3.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"ol-al-3\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/ol-al-3.gif\" width=\"519\" height=\"131\" \/><\/a><\/strong><\/p>\n<p>&nbsp;<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/li>\n<\/ul>\n<p>\u4ece\u4e0b\u9762\u7684\u5b9e\u4f8b\u80fd\u770b\u5230\u6234\u65af\uff0d\u9a6c\u4e01\u53cd\u5e94\u7684\u5b98\u80fd\u56e2\u9002\u7528\u6027\u975e\u5e38\u597d\u3002\u6240\u4ee5\u3001\u672c\u53cd\u5e94\u5e38\u7528\u5728\u5929\u7136\u5316\u5408\u7269\u7684\u5408\u6210\u4e2d\u3002\u6709\u4e9b\u60c5\u51b5\u4e0b\uff0c\uff08\u6dfb\u52a0\uff09\u6c34\u80fd\u63d0\u9ad8\u53cd\u5e94\u7684\u6548\u7387\u3002\u4f8b\u5b50[1]\n<p><strong><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/ol-al-5.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"ol-al-5\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/ol-al-5.gif\" width=\"274\" height=\"65\" \/><\/a><\/strong><\/p>\n<p>\u4f8b\u5b50[2]\n<p><strong><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/dess_martin_5.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"dess_martin_5\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/dess_martin_5.gif\" width=\"280\" height=\"100\" \/><\/a><\/strong><\/p>\n<p>Spongistatin2\u7684\u5408\u6210[3]\n<p><strong><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/dess_martin_6.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"alignnone aligncenter\" alt=\"dess_martin_6\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/dess_martin_6.gif\" width=\"587\" height=\"85\" \/><\/a><\/strong><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6b65\u9aa4<\/strong><\/li>\n<\/ul>\n<p>Dess-Martin periodinane (DMP)\u53ef\u4ee5\u4ece2-\u7898\u82ef\u7532\u9178\u6765\u5236\u5907\u3002\u6700\u521d\u539f\u6587\u62a5\u9053\u4e2d\u7684\u5408\u6210\u65b9\u6cd5\u51fa\u73b0\u91cd\u73fe\u6027\u7684\u95ee\u9898\u3002\u4e4b\u540e\u6539\u826f\u65b9\u6cd5\u52a0\u5165\u50ac\u5316\u5242TsOH\u89e3\u51b3\u4e86\u8fd9\u4e2a\u95ee\u9898\u3002<\/p>\n<p>\u5bf9IBX\u7684\u6c27\u5316\u3001\u7528Oxone [6]\u7684\u5408\u6210\u6cd5\u6bd4\u8f83\u7b80\u5355\u800c\u5b89\u5168\u3002<\/p>\n<p><strong><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/dess_martin_2.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter\" alt=\"dess_martin_2\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/01\/dess_martin_2.gif\" width=\"465\" height=\"226\" \/><\/a><\/strong><\/p>\n<p>\u53cd\u5e94\u540e\u7684\u540e\u5904\u7406\u975e\u5e38\u7b80\u5355\u3001\u7528\u4e8c\u4e59\u919a\u7a00\u91ca\u53cd\u5e94\u6df7\u5408\u6db2\u540e\u3001\u52a0\u8fdbaq.NaOH\u6216aq.NaHCO3\/Na2SO3\u540e\u8403\u53d6\u3002\u6d53\u7f29\u540e\u53ef\u4ee5\u76f4\u63a5\u7528\u67f1\u8272\u8c31\u6cd5\u5206\u79bb\u6216\u7eaf\u5316\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6280\u5de7<\/strong><\/li>\n<\/ul>\n<p>\u56e0\u4e3aDMP\u662f\u7206\u70b8\u6027\u5316\u5408\u7269\uff0c\u6b64\u836f\u54c1\u7684\u5e02\u552e\u4e00\u76f4\u7981\u6b62\u3002\u8fd1\u5e74\u968f\u7740\u65b0\u5236\u5907\u65b9\u6cd5\u7684\u51fa\u73b0\uff0cDMP\u91cd\u65b0\u6062\u590d\u751f\u4ea7\u3002\u4f46\u662f\uff0cDMP\u7684\u4ef7\u94b1\u975e\u5e38\u6602\u8d35\uff0c\u5927\u91cf\u4f7f\u7528\u65f6\uff0c\u9700\u8981\u5728\u81ea\u5df1\u914d\u5236\u3002\u5728\u540e\u5904\u7406\u65f6\uff0cDMP\u4e2d\u7684\u6c34\u5206\u7684\u591a\u5c11\u4f1a\u5f71\u54cd\u5176\u836f\u54c1\u7684\u53cd\u5e94\u6027\u3002DMP\u548c\u524d\u4f53(IBX)\u5c5e\u4e8e\u9ad8\u4ef7\u7898\u5316\u5408\u7269\u800c\u975e\u5e38\u5371\u9669\u3002\u56e0\u6b64\uff0c\u8c03\u6574DMP\u65f6\u9700\u8981\u6ce8\u610f\u53cd\u5e94\u7684\u5242\u91cf\u89c4\u6a21\u548c\u64cd\u4f5c\u6b65\u9aa4\u7b49\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53c2\u8003\u6587\u732e<\/strong><\/li>\n<\/ul>\n[1] \u5927\u5b66\u9662\u8b1b\u7fa9\u6709\u6a5f\u5316\u5b66 II p.174<br \/>\n[2] \u30d5\u30a1\u30eb\u30de\u30b7\u30a2\u00a0<strong>1996<\/strong>,\u00a0<em>32(9)<\/em><br \/>\n[3] Smith, A. B., III et al.\u00a0<em>Angew. Chem. Int. Ed.<\/em>\u00a0<strong>2001<\/strong>,\u00a0<em>40<\/em>, 196.\u00a0<a href=\"http:\/\/www3.interscience.wiley.com\/cgi-bin\/abstract\/76506144\/ABSTRACT\">[abstract]<\/a><br \/>\n[4] (a) Dess, D.B.; Martin, J. C.\u00a0<em>J. Org. Chem.<\/em>\u00a0<strong>1983<\/strong>,\u00a0<em>48<\/em>, 4155. (b)\u00a0<em>idem.<\/em>\u00a0<em>J. Am. Chem. Soc.<\/em>\u00a0<strong>1991<\/strong>,<em>113<\/em>, 7277. doi:<a href=\"http:\/\/dx.doi.org\/10.1021\/ja00019a027\">10.1021\/ja00019a027<\/a>\u00a0(c) Stevenson, P. J.; Treacy, A. B.\u00a0<em>J. C. S. Perkin Trans. 2<\/em><strong>1997<\/strong>, 589.<br \/>\n[5] Irekand, R.E.; Liu, L.\u00a0<em>J. Org . Chem.<\/em>\u00a0<strong>1993<\/strong>,\u00a0<em>58<\/em>, 2899. DOI:\u00a0<a href=\"http:\/\/dx.doi.org\/10.1021\/jo00062a040\">10.1021\/jo00062a040<\/a><br \/>\n[6] Frigerio, M.; Sntagostino, M.; Sputore, S.\u00a0<em>J. Org. Chem.<\/em>\u00a0<strong>1999<\/strong>,\u00a0<em>64<\/em>, 4537. DOI:\u00a0<a href=\"http:\/\/dx.doi.org\/10.1021\/jo9824596\">10.1021\/jo9824596<\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u76f8\u5173\u4e66\u7c4d<\/strong><\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u76f8\u5173\u94fe\u63a5<\/strong><\/li>\n<\/ul>\n<p>\u30fb<a href=\"http:\/\/orgchem.chem.uconn.edu\/namereact\/dessmartin.html\">Dess-Martin Periodinane Reagent<\/a><\/p>\n<p>\u30fb<a href=\"http:\/\/www.organic-chemistry.org\/frames.htm?http:\/\/www.organic-chemistry.org\/namedreactions\/dess-martin-oxidation.shtm\">Dess-Martin Oxidation<\/a>\u00a0(organic-chemistry.org)<\/p>\n<p>\u30fb<a href=\"http:\/\/en.wikipedia.org\/wiki\/Dess-Martin_periodinane\">Dess-Martin Periodinane<\/a>\u00a0(Wikipedia)<br \/>\n\u30fb<a href=\"http:\/\/www.orgsyn.org\/orgsyn\/prep.asp?prep=v77p0141\">Classical Preparation of DMP<\/a>\u00a0(Organic Synthesis)<br \/>\n\u30fb<a href=\"http:\/\/www.chem.harvard.edu\/groups\/myers\/handouts\/oxidation.pdf\">Oxidation<\/a>\u00a0(A.Myer&#8217;s Group:PDF)<br \/>\n\u30fb<a href=\"http:\/\/www.oc.tu-bs.de\/jahn\/Oxidation2.html\">Matrix of applications of some commonly used oxidation reagents<\/a> <\/p>\n","protected":false},"excerpt":{"rendered":"&nbsp; \u00a0\u6982\u8981 \u6234\u65af\uff0d\u9a6c\u4e01\u6c27\u5316\u5242Dess-Martin periodinane (DMP)\u53ef\u4ee5\u6c27\u5316\u9187\u5316\u5408\u7269\u3002 \u53cd\u5e94\u5728\u5ba4\u6e29\u5feb\u901f\u8fdb\u884c\uff0c\u53ef\u4ee5\u5c06\u4f2f\u9187\u6c27\u5316\u6210\u919b\u3002\u5bf9\u8f83\u5927\u4f4d\u963b\u7684\u9187\u3001\u53ca\u5728\u03b1\u4f4d\u6709\u4e0d\u5bf9\u79f0\u4e2d\u5fc3\u7684\u5916\u6d88\u65cb\u6df7\u5408\u7269\uff08\u6bd4\u5982\u7fb0\u57fa\u5316\u5408\u7269\uff09\u3001\u6216\u03b1,\u03b2-\u4e0d\u9971\u548c\u919b\u7684\u5408\u6210\u975e\u5e38\u6709\u6548\u3002\u6240\u4ee5\u672c\u53cd\u5e94\u88ab\u5e94\u7528\u5728\u591a\u79cd\u590d\u6742\u5316\u5408\u7269\u7684\u5408\u6210\u4e2d\u3002 \u672c\u53cd\u5e94\u80fd\u7528\u4e8e\u8bb8\u591a\u5bf9\u9178\u30fb\u78b1\u4e0d\u7a33\u5b9a\u7684\u5e95\u7269\u3002\u4ece\u53cd\u5e94\u673a\u7406\u6765\u8bf4\u4f1a\u4ea7\u751f\uff082\u5f53\u91cf\uff09\u4ee5\u4e0a\u7684\u918b\u9178\uff0c\u5373\u4f7f\u5e95\u7269\u5bf9\u751f\u6210\u7684\u918b\u9178\u4e0d\u7a33\u5b9a\u3001\u53ef\u7528\u5421\u5576\u7b49\u5f53\u7f13\u51b2\u5242\u907f\u514d\u8fd9\u4e00\u95ee\u9898\u3002 &nbsp; \u57fa\u672c\u6587\u732e \u30fbDess, D. B.; Martin, J. C.\u00a0J. Org. Chem.\u00a01983,\u00a048, 4155. DOI:\u00a010.1021\/jo00170a070 \u30fbDess, D. B.; Matrin, J. C.\u00a0J. Am. Chem. Soc.\u00a01991,\u00a0113, 7277. doi:10.1021\/ja00019a027 \u30fbStevenson, P. J.; Treacy, A. B.\u00a0J. C. S. Perkin Trans. 2\u00a01997, 589. DOI:\u00a010.1039\/a605253c &nbsp; \u53cd\u5e94\u673a\u7406 &nbsp; &nbsp; \u53cd\u5e94\u5b9e\u4f8b \u4ece\u4e0b\u9762\u7684\u5b9e\u4f8b\u80fd\u770b\u5230\u6234\u65af\uff0d\u9a6c\u4e01\u53cd\u5e94\u7684\u5b98\u80fd\u56e2\u9002\u7528\u6027\u975e\u5e38\u597d\u3002\u6240\u4ee5\u3001\u672c\u53cd\u5e94\u5e38\u7528\u5728\u5929\u7136\u5316\u5408\u7269\u7684\u5408\u6210\u4e2d\u3002\u6709\u4e9b\u60c5\u51b5\u4e0b\uff0c\uff08\u6dfb\u52a0\uff09\u6c34\u80fd\u63d0\u9ad8\u53cd\u5e94\u7684\u6548\u7387\u3002\u4f8b\u5b50[1] \u4f8b\u5b50[2] Spongistatin2\u7684\u5408\u6210[3] &nbsp; \u5b9e\u9a8c\u6b65\u9aa4 Dess-Martin periodinane (DMP)\u53ef\u4ee5\u4ece2-\u7898\u82ef\u7532\u9178\u6765\u5236\u5907\u3002\u6700\u521d\u539f\u6587\u62a5\u9053\u4e2d\u7684\u5408\u6210\u65b9\u6cd5\u51fa\u73b0\u91cd\u73fe\u6027\u7684\u95ee\u9898\u3002\u4e4b\u540e\u6539\u826f\u65b9\u6cd5\u52a0\u5165\u50ac\u5316\u5242TsOH\u89e3\u51b3\u4e86\u8fd9\u4e2a\u95ee\u9898\u3002 \u5bf9IBX\u7684\u6c27\u5316\u3001\u7528Oxone [6]\u7684\u5408\u6210\u6cd5\u6bd4\u8f83\u7b80\u5355\u800c\u5b89\u5168\u3002 \u53cd\u5e94\u540e\u7684\u540e\u5904\u7406\u975e\u5e38\u7b80\u5355\u3001\u7528\u4e8c\u4e59\u919a\u7a00\u91ca\u53cd\u5e94\u6df7\u5408\u6db2\u540e\u3001\u52a0\u8fdbaq.NaOH\u6216aq.NaHCO3\/Na2SO3\u540e\u8403\u53d6\u3002\u6d53\u7f29\u540e\u53ef\u4ee5\u76f4\u63a5\u7528\u67f1\u8272\u8c31\u6cd5\u5206\u79bb\u6216\u7eaf\u5316\u3002 &nbsp; \u5b9e\u9a8c\u6280\u5de7 \u56e0\u4e3aDMP\u662f\u7206\u70b8\u6027\u5316\u5408\u7269\uff0c\u6b64\u836f\u54c1\u7684\u5e02\u552e\u4e00\u76f4\u7981\u6b62\u3002\u8fd1\u5e74\u968f\u7740\u65b0\u5236\u5907\u65b9\u6cd5\u7684\u51fa\u73b0\uff0cDMP\u91cd\u65b0\u6062\u590d\u751f\u4ea7\u3002\u4f46\u662f\uff0cDMP\u7684\u4ef7\u94b1\u975e\u5e38\u6602\u8d35\uff0c\u5927\u91cf\u4f7f\u7528\u65f6\uff0c\u9700\u8981\u5728\u81ea\u5df1\u914d\u5236\u3002\u5728\u540e\u5904\u7406\u65f6\uff0cDMP\u4e2d\u7684\u6c34\u5206\u7684\u591a\u5c11\u4f1a\u5f71\u54cd\u5176\u836f\u54c1\u7684\u53cd\u5e94\u6027\u3002DMP\u548c\u524d\u4f53(IBX)\u5c5e\u4e8e\u9ad8\u4ef7\u7898\u5316\u5408\u7269\u800c\u975e\u5e38\u5371\u9669\u3002\u56e0\u6b64\uff0c\u8c03\u6574DMP\u65f6\u9700\u8981\u6ce8\u610f\u53cd\u5e94\u7684\u5242\u91cf\u89c4\u6a21\u548c\u64cd\u4f5c\u6b65\u9aa4\u7b49\u3002 &nbsp; \u53c2\u8003\u6587\u732e [1] \u5927\u5b66\u9662\u8b1b\u7fa9\u6709\u6a5f\u5316\u5b66 II p.174 [2] \u30d5\u30a1\u30eb\u30de\u30b7\u30a2\u00a01996,\u00a032(9) [3] Smith, A. B., III et al.\u00a0Angew. Chem. Int. Ed.\u00a02001,\u00a040, 196.\u00a0[abstract] [4] (a) Dess, D.B.; Martin, J. C.\u00a0J. Org. Chem.\u00a01983,\u00a048, 4155. (b)\u00a0idem.\u00a0J. Am. Chem. Soc.\u00a01991,113, 7277. doi:10.1021\/ja00019a027\u00a0(c) Stevenson, P. J.; Treacy, A. B.\u00a0J. C. S. Perkin Trans. 21997, 589. 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