{1(S)-12b(S)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl}carbamic acid benzyl ester

• 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)-12b(S)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl}carbamic acid benzyl ester
• 英文别名: benzyl N-[(1S,12bS)-4-oxo-2,3,6,7,12,12b-hexahydro-1H-indolo[2,3-a]quinolizin-1-yl]carbamate
• 化学式: C₂₃H₂₃N₃O₃
• 分子量: 389.454
• InChiKey: DFCIDXNZRQVAKH-UGKGYDQZSA-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)-12b(S)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl}carbamic acid benzyl ester 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以45%的产率得到(1R,12bR)-(1,2,3,4,6,7,12,12b-Octahydro-indolo[2,3-a]quinolizin-1-yl)-carbamic acid benzyl ester
  参考文献：
  名称：

  A short diastereoselective synthesis of 1-aminoindolo-[2,3-a]quinolizidines via an N-acyliminium ion cyclisation

  摘要：

  trans 1-Aminoindolo[2,3-a]quinolizidines were synthesised using an intramolecular Pictet-Spengler-like reaction. Starting from commercially available N-Cbz-L-glutamic acid, indoloquinolizidines were obtained in only five steps with good yields. This improved synthesis is the result of both a highly regioselective imide reduction and a highly diastereoselective reaction using N-acyliminium ions. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01922-x
• 作为产物：
  描述：

  N-苄氧羰基-L-谷氨酸 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 TEA 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 27.0h， 生成 {1(S)-12b(S)-4-oxo-1,2,3,4,6,7,12,12b-octahydro-indolo[2,3-a]quinolizin-1-yl}carbamic acid benzyl ester
  参考文献：
  名称：

  A short diastereoselective synthesis of 1-aminoindolo-[2,3-a]quinolizidines via an N-acyliminium ion cyclisation

  摘要：

  trans 1-Aminoindolo[2,3-a]quinolizidines were synthesised using an intramolecular Pictet-Spengler-like reaction. Starting from commercially available N-Cbz-L-glutamic acid, indoloquinolizidines were obtained in only five steps with good yields. This improved synthesis is the result of both a highly regioselective imide reduction and a highly diastereoselective reaction using N-acyliminium ions. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01922-x

文献信息

• Chiral Synthesis of <i>trans</i>-1-Aminoindolo[2,3-<i>a</i>]quinolizidine and <i>trans</i>-1-Aminobenzo[<i>a</i>]quinolizidine Derivatives from <scp>l</scp>-Pyroglutamic Acid
  作者：Yong Sup Lee、Dae Joo Cho、Sun Nam Kim、Jung Hoon Choi、Hokoon Park

  DOI：10.1021/jo9911950

  日期：1999.12.1
• A short diastereoselective synthesis of 1-aminoindolo-[2,3-a]quinolizidines via an N-acyliminium ion cyclisation
  作者：Pierre Ducrot、Claude Thal

  DOI：10.1016/s0040-4039(99)01922-x

  日期：1999.12

  trans 1-Aminoindolo[2,3-a]quinolizidines were synthesised using an intramolecular Pictet-Spengler-like reaction. Starting from commercially available N-Cbz-L-glutamic acid, indoloquinolizidines were obtained in only five steps with good yields. This improved synthesis is the result of both a highly regioselective imide reduction and a highly diastereoselective reaction using N-acyliminium ions. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.