1-Carbethoxy-4-iodo-3-(iodomethyl)indoline | 159118-05-5

• 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: 1-Carbethoxy-4-iodo-3-(iodomethyl)indoline
• 英文别名: 1-carbethoxy-3-(iodomethyl)-4-iodoindoline；Ethyl 4-iodo-3-(iodomethyl)-2,3-dihydroindole-1-carboxylate
• CAS: 159118-05-5
• 化学式: C₁₂H₁₃I₂NO₂
• 分子量: 457.05
• InChiKey: RZGXPZKUKWVSCV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Carbethoxy-4-iodo-3-(iodomethyl)indoline 在 N-溴代丁二酰亚胺(NBS) 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 氯仿 、 苯 为溶剂， 反应 3.0h， 生成 3-(Bromomethyl)-1-carbethoxy-4-iodoindole
  参考文献：
  名称：

  Synthesis and Reactions of 3-(Bromomethyl)-1-carbethoxy-4-iodoindole: The Preparation of 3,4-Differentially Substituted Indoles

  摘要：

  DOI：

  10.1021/jo00102a055
• 作为产物：
  描述：

  氯甲酸乙酯 、 1-Allyl-4-iodo-3-(iodomethyl)indoline 在 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以91%的产率得到1-Carbethoxy-4-iodo-3-(iodomethyl)indoline
  参考文献：
  名称：

  Synthesis of Polysubstituted Indoles and Indolines by Means of Zirconocene-Stabilized Benzyne Complexes

  摘要：

  The development of a new method for the regiospecific synthesis of polysubstituted indoles and indolines is reported. The key steps involve the generation of zirconocene-stabilized benzyne complexes and subsequent intramolecular olefin insertion reactions to provide tricyclic indoline zirconacycles. The zirconacyclic intermediates were cleaved with iodine to yield diiodo indolines, which were converted to a wide variety of indole and indoline products, such as analogs of tryptamine, serotonin, tryptophan, and the pharmacophore of CC-1065.

  DOI：

  10.1021/ja00105a021

文献信息

• Synthesis of Polysubstituted Indoles and Indolines by Means of Zirconocene-Stabilized Benzyne Complexes
  作者：Jeffrey H. Tidwell、Stephen L. Buchwald

  DOI：10.1021/ja00105a021

  日期：1994.12

  The development of a new method for the regiospecific synthesis of polysubstituted indoles and indolines is reported. The key steps involve the generation of zirconocene-stabilized benzyne complexes and subsequent intramolecular olefin insertion reactions to provide tricyclic indoline zirconacycles. The zirconacyclic intermediates were cleaved with iodine to yield diiodo indolines, which were converted to a wide variety of indole and indoline products, such as analogs of tryptamine, serotonin, tryptophan, and the pharmacophore of CC-1065.
• Synthesis and Reactions of 3-(Bromomethyl)-1-carbethoxy-4-iodoindole: The Preparation of 3,4-Differentially Substituted Indoles
  作者：Jeffrey H. Tidwell、Andrew J. Peat、Stephen L. Buchwald

  DOI：10.1021/jo00102a055

  日期：1994.11