1(R)-4'(S)-methoxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

• 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: 1(R)-4'(S)-methoxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester
• 英文别名: tert-butyl (4S)-4-(methoxycarbonylamino)-4-[(1R)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl]butanoate
• 化学式: C₂₁H₂₉N₃O₄
• 分子量: 387.479
• InChiKey: AUOQLZVDNOKKDW-QFBILLFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  92.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4(S)-methoxycarbonylamino-4-(methoxymethylcarbamoyl)butyric acid tert-butyl ester 在 lithium aluminium tetrahydride 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 1(R)-4'(S)-methoxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of Tetrahydro-β-carbolines and Studies of the Pictet–Spengler Reaction

  摘要：

  Tetrahydro-beta-carbolines have been prepared in a diastereomerically pure form by a short, efficient synthetic sequence consisting of reaction of cl-aminoaldehydes with tryptamine. A study was made of the major factors affecting the stereoselectivity of the Pictet-Spengler reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00165-4

文献信息

• Synthesis of Tetrahydro-β-carbolines and Studies of the Pictet–Spengler Reaction
  作者：Pierre Ducrot、Cherif Rabhi、Claude Thal

  DOI：10.1016/s0040-4020(00)00165-4

  日期：2000.4

  Tetrahydro-beta-carbolines have been prepared in a diastereomerically pure form by a short, efficient synthetic sequence consisting of reaction of cl-aminoaldehydes with tryptamine. A study was made of the major factors affecting the stereoselectivity of the Pictet-Spengler reaction. (C) 2000 Elsevier Science Ltd. All rights reserved.