3-[1-Chloro-1-ethoxycarbonyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester | 162853-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-[1-Chloro-1-ethoxycarbonyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester
• 英文别名: ethyl (3E)-3-(1-chloro-2-ethoxy-2-oxoethylidene)-2-oxoindole-1-carboxylate
• CAS: 162853-70-5
• 化学式: C₁₅H₁₄ClNO₅
• 分子量: 323.733
• InChiKey: WVJSNEYTQRMARB-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[1-Chloro-1-ethoxycarbonyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester 在 sodium ethanolate 、 二氯乙基铝 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 8,9-dimethyl-7,10-dihydro-5H-phenanthridin-6-one
  参考文献：
  名称：

  6-Chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates

  摘要：

  The Diels-Alder cycloaddition reaction of 3-chloromethylen-2-indolones 1 with a series of dienes 2 was studied in order to synthesize spirocyclohexenindolones 3 and 4. The reaction proceeded with good diastereoselectivity and regioselectivity. Chloro spirocyclohexenindolones 3 and 4 were transformed into 2-aminobiphenyl derivatives 5 by reacting with sodium ethoxide. Starting from the indolone 1c and 2,3-dimethylbutadiene the spiro compounds 3f and 4e were obtained. On treatment with sodium ethoxide, 3f was transformed into the phenanthridone derivatives 7 and 8. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00475-5
• 作为产物：
  描述：

  氯甲酸乙酯 、 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到3-[1-Chloro-1-ethoxycarbonyl-meth-(E)-ylidene]-2-oxo-2,3-dihydro-indole-1-carboxylic acid ethyl ester
  参考文献：
  名称：

  New indole derivatives. Synthesis of 3-acyl-1-carbethoxy-2-trifluoromethanesulfonylindoles and of substituted 2-vinylindoles

  摘要：

  3-Acyl-1-carbethoxy-2-trifluoromethanesulfonylindoles 6 and 3-acyl-2-vinylindoles 7 are synthesized from 3-[(1-chloro)alkylidene]indol-2(3H)-ones 2 via 1-carbethoxy-3-[(1-dimethylamino)alkylidene]indol-2(3H)-ones 4.

  DOI：

  10.1016/0040-4020(94)01092-e

文献信息

• A new synthetic procedure to spiro[cyclohexane-1,3′-indoline]-2′,4-diones
  作者：Egle Maria Beccalli、Francesca Clerici、Maria Luisa Gelmi

  DOI：10.1016/s0040-4020(03)00627-6

  日期：2003.6

  A new synthetic pathway to spiro[cyclohexane-1,3'-indoline]-2',4-diones was found starting from 3-chloromethylene-2-indolones 1 and Danishefsky's diene 2. Their synthesis consists of several steps involving the formation of the cycloadducts, the 6-chloro-4-trimethylsilyloxy-2-methoxyspiro[cyclohex-3-en-1,3'-indolin]-2'-one derivatives, transformed into spiro[cyclohexa-2,5-dienl,3'-indoline]-2',4-diones via 6-chloro-spiro[cyclohex-2-en-1,3'-indoline]-2',4-dione intermediates. The reduction of spiro[cyclohexa-2,5-dien-1,3'-indoline]-2',4-diones gave spiro[cyclohexane-1,3'-indoline]-2',4-diones 7. Using a 'one pot reaction', starting from 1 and 2, compounds 7 were obtained in satisfactory overall yield. (C) 2003 Elsevier Science Ltd. All rights reserved.