trans-N,N'-Bis(chloroacetyl)indigo | 150507-05-4

• 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: trans-N,N'-Bis(chloroacetyl)indigo
• 英文别名: N,N'-bis(chloroacetyl)indigo；(2E)-1-(2-chloroacetyl)-2-[1-(2-chloroacetyl)-3-oxoindol-2-ylidene]indol-3-one
• CAS: 150507-05-4
• 化学式: C₂₀H₁₂Cl₂N₂O₄
• 分子量: 415.232
• InChiKey: HESGUZREYUZSKH-ISLYRVAYSA-N

物化性质

• 沸点：
  559.9±50.0 °C(predicted)
• 密度：
  1.594±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  28
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  trans-N,N'-Bis(chloroacetyl)indigo 在 氧气 作用下， 以 甲苯 为溶剂， 反应 1440.0h， 生成 Chloro-acetic acid 1-(2-chloro-acetyl)-2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)-1H-indol-3-yl ester
  参考文献：
  名称：

  Photooxidation of N,N'-Diacylindigo Dyes

  摘要：

  Irradiation of N,N'-diacylindigo dyes in the presence of oxygen resulted in an unusual oxygen insertion/acyl transfer reaction. While this process occurred over many weeks at room temperature, at 100 degrees C it was complete in a few hours. In some cases the yield-of photooxidized product was virtually quantitative. The product structures were proved by spectroscopic methods and in one example by X-ray analysis. A series of mechanistic experiments led to the conclusion that at least the oxygen insertion part of the photooxidation process proceeded via a radical mechanism. The evidence included the following observations: (1) When the photooxidation was conducted in toluene, large amounts of benzyl hydroperoxide were produced; (2) the photooxidation could be achieved in the dark with a radical initiator; (3) attempts to generate the photooxidized product using singlet oxygen chemistry failed. The postulated radical mechanism is described.

  DOI：

  10.1021/jo00105a015
• 作为产物：
  描述：

  氯乙酰氯 、 1H,1H'-2,2'-Biindolylidene-3,3'-dione 在 2,6-二甲基吡啶 作用下， 以 乙酸丁酯 为溶剂， 反应 2.0h， 以15%的产率得到N-chloroacetylindigo
  参考文献：
  名称：

  Smith, Bradley D.; Paugam, Marie-France; Haller, Kenneth J., Journal of the Chemical Society. Perkin transactions II, 1993, # 2, p. 165 - 169

  摘要：

  DOI：

文献信息

• [1,3] Alkyl migration as a third type of N,N'-dialkanoylindigo photochemistry
  作者：Bradley D. Smith、David E. Alonso、Jeffrey T. Bien、John D. Zielinski、Sheridan L. Smith、Kenneth J. Haller

  DOI：10.1021/jo00075a059

  日期：1993.11
• Photooxidation of N,N'-Diacylindigo Dyes
  作者：Bradley D. Smith、David E. Alonso、Jeffrey T. Bien、Elise C. Metzler、Maoyu Shang、John M. Roosenberg

  DOI：10.1021/jo00105a015

  日期：1994.12

  Irradiation of N,N'-diacylindigo dyes in the presence of oxygen resulted in an unusual oxygen insertion/acyl transfer reaction. While this process occurred over many weeks at room temperature, at 100 degrees C it was complete in a few hours. In some cases the yield-of photooxidized product was virtually quantitative. The product structures were proved by spectroscopic methods and in one example by X-ray analysis. A series of mechanistic experiments led to the conclusion that at least the oxygen insertion part of the photooxidation process proceeded via a radical mechanism. The evidence included the following observations: (1) When the photooxidation was conducted in toluene, large amounts of benzyl hydroperoxide were produced; (2) the photooxidation could be achieved in the dark with a radical initiator; (3) attempts to generate the photooxidized product using singlet oxygen chemistry failed. The postulated radical mechanism is described.
• Smith, Bradley D.; Paugam, Marie-France; Haller, Kenneth J., Journal of the Chemical Society. Perkin transactions II, 1993, # 2, p. 165 - 169
  作者：Smith, Bradley D.、Paugam, Marie-France、Haller, Kenneth J.

  DOI：——

  日期：——