{1-[2-(1H-indol-3-yl)ethyl]-2,6-dioxopiperidin-3-yl}carbamic acid benzyl ester | 256512-42-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {1-[2-(1H-indol-3-yl)ethyl]-2,6-dioxopiperidin-3-yl}carbamic acid benzyl ester
• 英文别名: benzyl N-[(3S)-1-[2-(1H-indol-3-yl)ethyl]-2,6-dioxopiperidin-3-yl]carbamate
• CAS: 256512-42-2
• 化学式: C₂₃H₂₃N₃O₄
• 分子量: 405.453
• InChiKey: LLPHWHRHVKBVRN-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  91.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {1-[2-(1H-indol-3-yl)ethyl]-2,6-dioxopiperidin-3-yl}carbamic acid benzyl ester 在 盐酸 、 sodium tetrahydroborate 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 ((1R,12bS)-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
• 作为产物：
  描述：

  色胺 、 N-苄氧羰基-L-谷氨酸 在 4-二甲氨基吡啶 、 TEA 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 以67%的产率得到{1-[2-(1H-indol-3-yl)ethyl]-2,6-dioxopiperidin-3-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

• 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.