methyl (R)-2-amino-3-(2-(3,4-dimethoxybenzyl)-1H-indol-3-yl)propanoate | 1158815-30-5

• 分子结构分类: 有机化合物
• 英文名称: methyl (R)-2-amino-3-(2-(3,4-dimethoxybenzyl)-1H-indol-3-yl)propanoate
• CAS: 1158815-30-5
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: POQXLCOUXMQKKL-MRXNPFEDSA-N

物化性质

• 沸点：
  540.2±45.0 °C(predicted)
• 密度：
  1.217±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.82
• 重原子数：
  27.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.57
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  methyl (1S,3R)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate hydrochloride 在 盐酸 、 锌 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 8.0h， 以45%的产率得到(1S,3R)-1-(3,4-dimethoxyphenyl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Syntheses of chiral 1,3-disubstituted tetrahydro-β-carbolines via CIAT process: highly stereoselective Pictet–Spengler reaction of d-tryptophan ester hydrochlorides with various aldehydes

  摘要：

  A highly stereoselective Pictet-Spengler reaction of D-tryptophan methyl ester hydrochloride 1-HCl with various aldehydes via a CIAT (crystallization-induced asymmetric transformation) process is described. It was revealed that the CIAT process should be performed in a mixed solvent of nitromethane and toluene, and a fine tuning of the ratio of nitromethane and toluene for each epimer Mixture of 2-HCl was necessary in order to get as high yields and stereoselectivities as possible. Enantiomerically pure cis (or trans) 1,3-disubstituted tetrahydro-beta-carbolines 2a-2v were obtained by recrystallization or flash chromatography after neutralization of the corresponding hydrochloride salts cis-2-HCl or trans-2-HCl. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.01.026