(1S,2S,3R)-2-(hydroxyamino)-3-(1H-indol-3-yl)-1,3-diphenylpropan-1-ol | 1278574-84-7

• 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-(hydroxyamino)-3-(1H-indol-3-yl)-1,3-diphenylpropan-1-ol
• CAS: 1278574-84-7
• 化学式: C₂₃H₂₂N₂O₂
• 分子量: 358.44
• InChiKey: ODGFIRDBQIPIDB-VJBWXMMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  68.3
• 氢给体数：
  4
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯甲醛 在 盐酸 、 copper(I) trifluoromethanesulfonate benzene 、 六氟异丙醇 、 2,4-二溴-6-[[[[(4S,5S)-4,5-二氢-4,5-二苯基-1-甲苯磺酰基-1H-咪唑-2-基]甲基][(S)-1-苯乙基]氨基]甲基]苯酚 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 24.0h， 生成 (1S,2S,3R)-2-(hydroxyamino)-3-(1H-indol-3-yl)-1,3-diphenylpropan-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.