benzyl (1S,3S)-1-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 1171123-81-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: benzyl (1S,3S)-1-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1171123-81-1
• 化学式: C₂₇H₂₆N₂O₂
• 分子量: 410.516
• InChiKey: WOJATOGGSZPUAP-DQEYMECFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  54.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯丙醛 、 L-色氨酸苯甲酯 在 三氟乙酸 、 碳酸氢钠 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 benzyl (1S,3S)-1-(2-phenylethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate 、
  参考文献：
  名称：

  Unexpected cis selectivity in the Pictet–Spengler reaction

  摘要：

  Whilst cis:trans selectivity of about 4:1 can be obtained from Pictet-Spengler reactions between tryptophan methyl esters and aldehydes using conditions of kinetic control, much higher cis selectivity (>95:5) can be obtained when both the tryptophan derivative and the aldehyde possess a Suitable pi-system: preliminary results oil the scope and limitations of this exceptional stereocontrol are presented in this Letter. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.03.121

文献信息

• Unexpected cis selectivity in the Pictet–Spengler reaction
  作者：Patrick D. Bailey、Mark A. Beard、Theresa R. Phillips

  DOI：10.1016/j.tetlet.2009.03.121

  日期：2009.7

  Whilst cis:trans selectivity of about 4:1 can be obtained from Pictet-Spengler reactions between tryptophan methyl esters and aldehydes using conditions of kinetic control, much higher cis selectivity (>95:5) can be obtained when both the tryptophan derivative and the aldehyde possess a Suitable pi-system: preliminary results oil the scope and limitations of this exceptional stereocontrol are presented in this Letter. (C) 2009 Elsevier Ltd. All rights reserved.