N,N-diallyl-2-bromo-5-methoxyaniline | 144085-17-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N,N-diallyl-2-bromo-5-methoxyaniline
• 英文别名: 2-bromo-5-methoxy-N,N-bis(prop-2-enyl)aniline
• CAS: 144085-17-6
• 化学式: C₁₃H₁₆BrNO
• 分子量: 282.18
• InChiKey: ZPRIUBYMGRLXQA-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：

  N,N-diallyl-2-bromo-5-methoxyaniline 在 zirconocene methyl chloride 、 碘 、 叔丁基锂 、 三溴化硼 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 1-allyl-4-iodo-1,2,7,7a-tetrahydrocycloprop<1,2-c>indol-4-one
  参考文献：
  名称：

  A new approach to the synthesis of the CC-1065/duocarmycin pharmacophore

  摘要：

  The spirocyclic 1,2,7,7a-tetrahydrocycloprop-[1,2-c]indol-4-one subunit of CC-1065 and duocarmycin A, which comprises the common pharmacophore of the two antibiotics, has been efficiently synthesized in six steps from readily available starting materials. The key step of the synthesis utilizes a zirconocene-stabilized benzyne complex.

  DOI：

  10.1021/jo00050a003
• 作为产物：
  描述：

  4-溴-3-硝基苯甲醚 在 盐酸 、 铁粉 、 碳酸氢钠 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N,N-diallyl-2-bromo-5-methoxyaniline
  参考文献：
  名称：

  A new approach to the synthesis of the CC-1065/duocarmycin pharmacophore

  摘要：

  The spirocyclic 1,2,7,7a-tetrahydrocycloprop-[1,2-c]indol-4-one subunit of CC-1065 and duocarmycin A, which comprises the common pharmacophore of the two antibiotics, has been efficiently synthesized in six steps from readily available starting materials. The key step of the synthesis utilizes a zirconocene-stabilized benzyne complex.

  DOI：

  10.1021/jo00050a003

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.
• A new approach to the synthesis of the CC-1065/duocarmycin pharmacophore
  作者：Jeffrey H. Tidwell、Stephen L. Buchwald

  DOI：10.1021/jo00050a003

  日期：1992.11

  The spirocyclic 1,2,7,7a-tetrahydrocycloprop-[1,2-c]indol-4-one subunit of CC-1065 and duocarmycin A, which comprises the common pharmacophore of the two antibiotics, has been efficiently synthesized in six steps from readily available starting materials. The key step of the synthesis utilizes a zirconocene-stabilized benzyne complex.