ethyl (3E)-3-(chloromethylidene)-2-oxoindole-1-carboxylate | 162853-69-2

• 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: ethyl (3E)-3-(chloromethylidene)-2-oxoindole-1-carboxylate
• CAS: 162853-69-2
• 化学式: C₁₂H₁₀ClNO₃
• 分子量: 251.669
• InChiKey: PRKAKZRUXBDNNA-VQHVLOKHSA-N

物化性质

• 沸点：
  346.9±52.0 °C(Predicted)
• 密度：
  1.460±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl (3E)-3-(chloromethylidene)-2-oxoindole-1-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 甲苯 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 23.0h， 生成 spiro[cyclohexane-1,3’-indoline]-2’,4-dione
  参考文献：
  名称：

  A new synthetic procedure to spiro[cyclohexane-1,3′-indoline]-2′,4-diones

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(03)00627-6
• 作为产物：
  描述：

  (E)-3-chloromethylene-indolin-2-one 、 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78%的产率得到ethyl (3E)-3-(chloromethylidene)-2-oxoindole-1-carboxylate
  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

• 6-Chloro-spirocyclohexenindol-2-ones: an unusual ring transformation to ethyl 2-(cyclohexa-1,4-dienyl)phenylcarbamates
  作者：Egle Maria Beccalli、Francesca Clerici、Maria Luisa Gelmi

  DOI：10.1016/s0040-4020(99)00475-5

  日期：1999.7

  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.
• 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.
• New indole derivatives. Synthesis of 3-acyl-1-carbethoxy-2-trifluoromethanesulfonylindoles and of substituted 2-vinylindoles
  作者：Egle M Beccalli、Alessandro Marchesini

  DOI：10.1016/0040-4020(94)01092-e

  日期：1995.2

  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.