{"id":3464,"date":"2014-12-22T20:30:53","date_gmt":"2014-12-22T12:30:53","guid":{"rendered":"\/\/www.gsbet888.com\/?p=3464"},"modified":"2019-08-02T18:55:58","modified_gmt":"2019-08-02T10:55:58","slug":"bredereck%e5%99%81%e5%94%91%e5%90%88%e6%88%90%e6%b3%95bredereck-oxazole-synthesis","status":"publish","type":"post","link":"\/\/www.gsbet888.com\/reactions\/%e7%bc%a9%e5%90%88%e5%8f%8d%e5%ba%94\/2014\/12\/bredereck%e5%99%81%e5%94%91%e5%90%88%e6%88%90%e6%b3%95bredereck-oxazole-synthesis.html","title":{"rendered":"Bredereck\u5641\u5511\u5408\u6210\u6cd5(Bredereck Oxazole Synthesis)"},"content":{"rendered":"<ul>\n<li><strong>\u6982\u8981<\/strong><\/li>\n<\/ul>\n<p>\u03b1-\u5364\u4ee3\u916e\u4e0e\u7532\u9170\u80fa\uff08\u6216\u8132\uff09\u5408\u6210\u5641\u5511\u7684\u624b\u6cd5\u3002\u7528\u786b\u4ee3\u9170\u80fa\u4ee3\u66ff\u7532\u9170\u80fa\uff0c\u53ef\u4ee5\u5f97\u5230\u567b\u5511\u7c7b\u4ea7\u7269\u3002<\/p>\n<p>\u5641\u5511\u662f\u4e00\u4e2a\u82b3\u9999\u6027\u5316\u5408\u7269\uff0c\u4f46\u662f\u5176\u82b3\u9999\u6027\u4e0d\u53ca\u567b\u5511\u3002\u5641\u5511\u4e5f\u662f\u4e00\u4e2a\u5f31\u78b1\uff0c\u5176\u5171\u8f6d\u9178\u7684p<i>K<\/i><sub>a<\/sub>\u503c\u662f0.8\uff0c\u76f8\u6bd4\u800c\u8a00\uff0c\u54aa\u5511\u7684\u5171\u8f6d\u9178\u7684p<i>K<\/i><sub>a<\/sub>\u662f7\u3002<\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u57fa\u672c\u6587\u732e<\/strong><\/li>\n<\/ul>\n<ul>\n<li>H. Bredereck, Bangert,\u00a0R. <em>Angew. Chem. Int. Ed.<\/em> <strong>1962,<\/strong> 1, 662. DOI:\u00a0<a class=\"ext-link ext-icon-2\" title=\"\" href=\"http:\/\/dx.doi.org\/10.1002\/anie.196206622\" rel=\"external\" data-wpel-target=\"_blank\">10.1002\/anie.196206622<\/a><\/li>\n<\/ul>\n<p>\u5f00\u53d1\u7684\u5386\u53f2\u80cc\u666f<\/p>\n<p>1962\u5e74\u5fb7\u56fd\u5316\u5b66\u5bb6Bredereck\u9996\u5148\u62a5\u9053\u4e86\u6b64\u5408\u6210\u624b\u6cd5\u3002\u4f7f\u7528\u7532\u9170\u80fa\u548c\u03b1-\u4e8c\u916e\u53cd\u5e94\u7684\u8bdd\u53ef\u4ee5\u5f97\u5230\u54aa\u5511\uff0c\u800c\u662f\u75281,3-\u4e8c\u7fb0\u57fa\u5316\u5408\u7269\u7684\u8bdd\u53ef\u751f\u6210\u5627\u5576\u3002<\/p>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/11\/2014-09-10_22-12-31.png\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter size-full wp-image-3465\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/11\/2014-09-10_22-12-31.png\" alt=\"2014-09-10_22-12-31\" width=\"139\" height=\"206\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u673a\u7406<\/strong><\/li>\n<\/ul>\n<p><a href=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/11\/bred_oxazole_2.gif\"><img loading=\"lazy\" decoding=\"async\" class=\"aligncenter wp-image-3466 size-full\" src=\"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/11\/bred_oxazole_2.gif\" alt=\"bred_oxazole_2\" width=\"388\" height=\"170\" \/><\/a><\/p>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53cd\u5e94\u5b9e\u4f8b<\/strong><\/li>\n<\/ul>\n<p>\u5bf9\u4e8e\u5641\u5511\uff0c\u7ecf\u5178\u7684\u6709\u673a\u5408\u6210\u65b9\u6cd5\u8fd8\u6709\u4ee5\u4e0b\u4e24\u79cd\uff1a<\/p>\n<ol>\n<li>Robinson-Gabriel\u5408\u6210\uff1a\u5bf92-\u9170\u6c28\u916e\u8131\u6c34\u5f97\u5230\u5641\u5511\u3002<\/li>\n<li>\u8d39\u6b47\u5c14\u5641\u5511\u5408\u6210\uff08en:Fischer oxazole synthesis\uff09\uff1a\u901a\u8fc7\u6c30\u9187\u548c\u919b\u5408\u6210\u5641\u5511\u3002<\/li>\n<\/ol>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6b65\u9aa4<\/strong><\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u5b9e\u9a8c\u6280\u5de7<\/strong><\/li>\n<\/ul>\n<p>&nbsp;<\/p>\n<ul>\n<li><strong>\u53c2\u8003\u6587\u732e<\/strong><\/li>\n<\/ul>\n<ol class=\"references\">\n<li id=\"cite_note-1\">\u00a0<span class=\"reference-text\">Zoltewicz, J. A. &amp; Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978).<\/span><\/li>\n<li id=\"cite_note-2\"><span class=\"reference-text\">Heterocyclic Chemistry TL Gilchrist, The Bath press 1985 ISBN 0-582-01421-2<\/span><\/li>\n<li id=\"cite_note-3\">\u00a0<span class=\"reference-text\"><i>A new consecutive three-component oxazole synthesis by an amidation\u2013coupling\u2013cycloisomerization (ACCI) sequence<\/i> Eugen Merkul and Thomas J. J. M\u00fcller <i>Chem. Commun.<\/i>,<b>2006<\/b>, 4817 &#8211; 4819, doi:10.1039\/b610839c<\/span><\/li>\n<li id=\"cite_note-4\">\u00a0<span class=\"reference-text\"><i>Fully Automated Continuous Flow Synthesis of 4,5-Disubstituted Oxazoles<\/i> Marcus Baumann, Ian R. Baxendale, Steven V. Ley, Christoper D. Smith, and Geoffrey K. TranmerOrg. Lett.; <b>2006<\/b>; 8(23) pp 5231 &#8211; 5234; (Letter) doi:10.1021\/ol061975c<\/span><\/li>\n<li id=\"cite_note-5\">\u00a0<span class=\"reference-text\"><i>Ceric Ammonium Nitrate Promoted Oxidation of Oxazoles<\/i> David A. Evans, Pavel Nagorny, and Risheng Xu Org. Lett.; <b>2006<\/b>; 8(24) pp 5669 &#8211; 5671; (Letter)doi:10.1021\/ol0624530<\/span><\/li>\n<\/ol>\n<p>&nbsp; <\/p>\n","protected":false},"excerpt":{"rendered":"\u6982\u8981 \u03b1-\u5364\u4ee3\u916e\u4e0e\u7532\u9170\u80fa\uff08\u6216\u8132\uff09\u5408\u6210\u5641\u5511\u7684\u624b\u6cd5\u3002\u7528\u786b\u4ee3\u9170\u80fa\u4ee3\u66ff\u7532\u9170\u80fa\uff0c\u53ef\u4ee5\u5f97\u5230\u567b\u5511\u7c7b\u4ea7\u7269\u3002 \u5641\u5511\u662f\u4e00\u4e2a\u82b3\u9999\u6027\u5316\u5408\u7269\uff0c\u4f46\u662f\u5176\u82b3\u9999\u6027\u4e0d\u53ca\u567b\u5511\u3002\u5641\u5511\u4e5f\u662f\u4e00\u4e2a\u5f31\u78b1\uff0c\u5176\u5171\u8f6d\u9178\u7684pKa\u503c\u662f0.8\uff0c\u76f8\u6bd4\u800c\u8a00\uff0c\u54aa\u5511\u7684\u5171\u8f6d\u9178\u7684pKa\u662f7\u3002 &nbsp; \u57fa\u672c\u6587\u732e H. Bredereck, Bangert,\u00a0R. Angew. Chem. Int. Ed. 1962, 1, 662. DOI:\u00a010.1002\/anie.196206622 \u5f00\u53d1\u7684\u5386\u53f2\u80cc\u666f 1962\u5e74\u5fb7\u56fd\u5316\u5b66\u5bb6Bredereck\u9996\u5148\u62a5\u9053\u4e86\u6b64\u5408\u6210\u624b\u6cd5\u3002\u4f7f\u7528\u7532\u9170\u80fa\u548c\u03b1-\u4e8c\u916e\u53cd\u5e94\u7684\u8bdd\u53ef\u4ee5\u5f97\u5230\u54aa\u5511\uff0c\u800c\u662f\u75281,3-\u4e8c\u7fb0\u57fa\u5316\u5408\u7269\u7684\u8bdd\u53ef\u751f\u6210\u5627\u5576\u3002 &nbsp; \u53cd\u5e94\u673a\u7406 &nbsp; \u53cd\u5e94\u5b9e\u4f8b \u5bf9\u4e8e\u5641\u5511\uff0c\u7ecf\u5178\u7684\u6709\u673a\u5408\u6210\u65b9\u6cd5\u8fd8\u6709\u4ee5\u4e0b\u4e24\u79cd\uff1a Robinson-Gabriel\u5408\u6210\uff1a\u5bf92-\u9170\u6c28\u916e\u8131\u6c34\u5f97\u5230\u5641\u5511\u3002 \u8d39\u6b47\u5c14\u5641\u5511\u5408\u6210\uff08en:Fischer oxazole synthesis\uff09\uff1a\u901a\u8fc7\u6c30\u9187\u548c\u919b\u5408\u6210\u5641\u5511\u3002 &nbsp; \u5b9e\u9a8c\u6b65\u9aa4 &nbsp; \u5b9e\u9a8c\u6280\u5de7 &nbsp; \u53c2\u8003\u6587\u732e \u00a0Zoltewicz, J. A. &amp; Deady, L. W. Quaternization of heteroaromatic compounds. Quantitative aspects. Adv. Heterocycl. Chem. 22, 71-121 (1978). Heterocyclic Chemistry TL Gilchrist, The Bath press 1985 ISBN 0-582-01421-2 \u00a0A new consecutive three-component oxazole synthesis by an amidation\u2013coupling\u2013cycloisomerization (ACCI) sequence Eugen Merkul and Thomas J. J. M\u00fcller Chem. Commun.,2006, 4817 &#8211; 4819, doi:10.1039\/b610839c \u00a0Fully Automated Continuous Flow Synthesis of 4,5-Disubstituted Oxazoles Marcus Baumann, Ian R. Baxendale, Steven V. Ley, Christoper D. Smith, and Geoffrey K. TranmerOrg. Lett.; [&hellip;]","protected":false},"author":5,"featured_media":3554,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"jetpack_post_was_ever_published":false,"_jetpack_newsletter_access":"","_jetpack_dont_email_post_to_subs":false,"_jetpack_newsletter_tier_id":0,"_jetpack_memberships_contains_paywalled_content":false,"_jetpack_memberships_contains_paid_content":false,"footnotes":"","jetpack_publicize_message":"","jetpack_publicize_feature_enabled":true,"jetpack_social_post_already_shared":true,"jetpack_social_options":{"image_generator_settings":{"template":"highway","enabled":false},"version":2}},"categories":[309],"tags":[640],"jetpack_publicize_connections":[],"jetpack_featured_media_url":"https:\/\/assets.www.gsbet888.com\/uploads\/2014\/11\/2014-09-10_22-14-49.png","jetpack_shortlink":"https:\/\/wp.me\/p96op1-TS","jetpack_sharing_enabled":true,"_links":{"self":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/3464"}],"collection":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/users\/5"}],"replies":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/comments?post=3464"}],"version-history":[{"count":2,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/3464\/revisions"}],"predecessor-version":[{"id":28015,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/posts\/3464\/revisions\/28015"}],"wp:featuredmedia":[{"embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media\/3554"}],"wp:attachment":[{"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/media?parent=3464"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/categories?post=3464"},{"taxonomy":"post_tag","embeddable":true,"href":"\/\/www.gsbet888.com\/wp-json\/wp\/v2\/tags?post=3464"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}