(1S,2S,3R)-2-amino-1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenylpropan-1-ol | 1278575-06-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (1S,2S,3R)-2-amino-1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenylpropan-1-ol
• CAS: 1278575-06-6
• 化学式: C₂₃H₂₁BrN₂O
• 分子量: 421.337
• InChiKey: TTWWNPANCDGVPW-VJBWXMMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62
• 氢给体数：
  3
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R)-2-amino-1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenylpropan-1-ol 在 咪唑 、 magnesium sulfate 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 (S)-(4-bromophenyl)-[(1S,3S,4R)-1,4-diphenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-3-yl]methanol
  参考文献：
  名称：

  Easy Access to Fully Functionalized Chiral Tetrahydro-β-Carboline Alkaloids

  摘要：

  A four-step synthetic route to fully substituted chiral tetrahydro-beta-carbolines (THBCs) is described. Starting from the (R,S,S)-Friedel-Crafts/Henry adduct obtained from three-component coupling of an indole, nitroalkene, and aldehyde catalyzed by imidazoline-aminophenol-CuOTf, the (1S,3S,4R)-THBCs were readily synthesized in a three-step operation including reduction of the nitro-functionality and Pictet-Spengler cyclization.

  DOI：

  10.1021/jo1025833
• 作为产物：
  描述：

  (1S,2S,3R)-1-(4-bromophenyl)-3-(1H-indol-3-yl)-2-nitro-3-phenylpropan-1-ol 在 盐酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 18.0h， 以99%的产率得到(1S,2S,3R)-2-amino-1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenylpropan-1-ol
  参考文献：
  名称：

  Easy Access to Fully Functionalized Chiral Tetrahydro-β-Carboline Alkaloids

  摘要：

  A four-step synthetic route to fully substituted chiral tetrahydro-beta-carbolines (THBCs) is described. Starting from the (R,S,S)-Friedel-Crafts/Henry adduct obtained from three-component coupling of an indole, nitroalkene, and aldehyde catalyzed by imidazoline-aminophenol-CuOTf, the (1S,3S,4R)-THBCs were readily synthesized in a three-step operation including reduction of the nitro-functionality and Pictet-Spengler cyclization.

  DOI：

  10.1021/jo1025833

文献信息

• Easy Access to Fully Functionalized Chiral Tetrahydro-β-Carboline Alkaloids
  作者：Takayoshi Arai、Makiko Wasai、Naota Yokoyama

  DOI：10.1021/jo1025833

  日期：2011.4.15

  A four-step synthetic route to fully substituted chiral tetrahydro-beta-carbolines (THBCs) is described. Starting from the (R,S,S)-Friedel-Crafts/Henry adduct obtained from three-component coupling of an indole, nitroalkene, and aldehyde catalyzed by imidazoline-aminophenol-CuOTf, the (1S,3S,4R)-THBCs were readily synthesized in a three-step operation including reduction of the nitro-functionality and Pictet-Spengler cyclization.