2-bromo-4-methoxy-N,N-diallylaniline | 159766-74-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-bromo-4-methoxy-N,N-diallylaniline
• 英文别名: N,N-diallyl-2-bromo-4-methoxyaniline；2-bromo-4-methoxy-N,N-bis(prop-2-enyl)aniline
• CAS: 159766-74-2
• 化学式: C₁₃H₁₆BrNO
• 分子量: 282.18
• InChiKey: SPFKFNMQKIGGMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-4-methoxy-N,N-diallylaniline 在 zirconocene methyl chloride 、 碘 、 叔丁基锂 作用下， 生成 1-allyl-4-iodo-3-(iodomethyl)-5-methoxyindoline
  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
• 作为产物：
  描述：

  2-溴-4-甲氧基苯胺 、 3-溴丙烯 在 sodium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以88%的产率得到2-bromo-4-methoxy-N,N-diallylaniline
  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

• A Versatile Synthesis of 3-Substituted Indolines and Indoles
  作者：Dawei Zhang、Lanny S. Liebeskind

  DOI：10.1021/jo960304x

  日期：1996.1.1
• 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.