(1S,2S,3R)-2-amino-3-(1H-indol-3-yl)-1-phenyloctan-1-ol | 1278575-08-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (1S,2S,3R)-2-amino-3-(1H-indol-3-yl)-1-phenyloctan-1-ol
• CAS: 1278575-08-8
• 化学式: C₂₂H₂₈N₂O
• 分子量: 336.477
• InChiKey: AKOZGRXIPNQZAH-COPCDDAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 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-3-(1H-indol-3-yl)-1-phenyloctan-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 27.0h， 生成 (S)-[(1S,3S,4R)-4-pentyl-1-phenyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-3-yl]-phenylmethanol
  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)-3-(1H-indol-3-yl)-2-nitro-1-phenyloctan-1-ol 在 盐酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以98%的产率得到(1S,2S,3R)-2-amino-3-(1H-indol-3-yl)-1-phenyloctan-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.