(1S,2S,3R)-1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenyl-1-triethylsilyloxypropan-2-amine | 1278575-14-6

• 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)-1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenyl-1-triethylsilyloxypropan-2-amine
• CAS: 1278575-14-6
• 化学式: C₂₉H₃₅BrN₂OSi
• 分子量: 535.599
• InChiKey: SGTGDLOJYRWZLH-ULNSLHSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.15
• 重原子数：
  34
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2S,3R)-1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenyl-1-triethylsilyloxypropan-2-amine 、 4-氯苯甲醛 在 magnesium sulfate 、 三氟乙酸 作用下， 以 氯仿 为溶剂， 反应 24.0h， 以70%的产率得到(S)-(4-bromophenyl)-[(1S,3S,4R)-1-(4-chlorophenyl)-4-phenyl-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 咪唑 、 盐酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (1S,2S,3R)-1-(4-bromophenyl)-3-(1H-indol-3-yl)-3-phenyl-1-triethylsilyloxypropan-2-amine
  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.