1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one | 153037-23-1

• 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: 1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one
• 英文别名: 1(S)-12b(R)-(4-oxo-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-1-yl)carbamic acid benzyl ester；benzyl N-[(1S,12bR)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-1-yl]carbamate
• CAS: 153037-23-1
• 化学式: C₂₃H₂₃N₃O₃
• 分子量: 389.454
• InChiKey: DFCIDXNZRQVAKH-SIKLNZKXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以68%的产率得到1-(S)-amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one
  参考文献：
  名称：

  Stereospecific pictet-spengler reaction: synthesis of cis (+)-(1S, 12bR)-1-aminoindoloquinolizidine from a pure α-(S)-aminoaldehyde derivative

  摘要：

  Pictet-Spengler reaction provides cis (+)-1-(S)-aminoindolo[2,3-a]quinolizidine in an enantio- and diastereoselective manner, using an alpha-aminoaldehyde derived from L-glutamic acid.

  DOI：

  10.1016/s0040-4020(01)96265-9
• 作为产物：
  描述：

  N-苄氧羰基-L-谷氨酸γ-叔丁酯 在 N-甲基吗啉 、 lithium aluminium tetrahydride 、 sodium methylate 、 三氟乙酸 、 氯甲酸异丁酯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 31.17h， 生成 1-(S)-(N-carbobenzyloxy)amino-1,2,3,4,6,7,12,12b-(R)-octahydroindolo<2,3-a>quinolizidin-4-one
  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.
• Stereospecific pictet-spengler reaction: synthesis of cis (+)-(1S, 12bR)-1-aminoindoloquinolizidine from a pure α-(S)-aminoaldehyde derivative
  作者：Patricia Melnyk、Pierre Ducrot、Claude Thal

  DOI：10.1016/s0040-4020(01)96265-9

  日期：1993.9

  Pictet-Spengler reaction provides cis (+)-1-(S)-aminoindolo[2,3-a]quinolizidine in an enantio- and diastereoselective manner, using an alpha-aminoaldehyde derived from L-glutamic acid.