N-(tert-butoxycarbonyl)-4,4-dihydro-2-methyl-1H-benz[g]indole | 180516-78-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(tert-butoxycarbonyl)-4,4-dihydro-2-methyl-1H-benz[g]indole
• 英文别名: Tert-butyl 2-methyl-4,5-dihydrobenzo[g]indole-1-carboxylate
• CAS: 180516-78-3
• 化学式: C₁₈H₂₁NO₂
• 分子量: 283.37
• InChiKey: IBQCFAPHYBOMQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(tert-butoxycarbonyl)-4,4-dihydro-2-methyl-1H-benz[g]indole 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 反应 0.67h， 以48%的产率得到N-(tert-butoxycarbonyl)-2-methyl-1H-benz[g]indole
  参考文献：
  名称：

  A General Synthesis of Pyrroles and Fused Pyrrole Systems from Ketones and Amino Acids

  摘要：

  The lithium enolates of ketones react with BOC-alpha-amino aldehydes and BOC-alpha-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from ol-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.

  DOI：

  10.1021/jo960401q
• 作为产物：
  描述：

  Boc-L-丙氨醛 在 盐酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(tert-butoxycarbonyl)-4,4-dihydro-2-methyl-1H-benz[g]indole
  参考文献：
  名称：

  A General Synthesis of Pyrroles and Fused Pyrrole Systems from Ketones and Amino Acids

  摘要：

  The lithium enolates of ketones react with BOC-alpha-amino aldehydes and BOC-alpha-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from ol-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.

  DOI：

  10.1021/jo960401q

文献信息

• A General Synthesis of Pyrroles and Fused Pyrrole Systems from Ketones and Amino Acids
  作者：Pamela Nagafuji、Mark Cushman

  DOI：10.1021/jo960401q

  日期：1996.1.1

  The lithium enolates of ketones react with BOC-alpha-amino aldehydes and BOC-alpha-amino ketones to afford aldol intermediates that cyclize under acidic conditions to yield pyrroles. The BOC-amino aldehydes and ketones are readily available from ol-amino acids. The method allows incorporation of a wide variety of substituents at any of the five atoms of the pyrrole ring and is also suitable for the preparation of fused pyrrole systems.