(R)-N-benzyloxycarbonyl-2-(4-pentenyl)pyrrolidine | 218914-64-8

• 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: (R)-N-benzyloxycarbonyl-2-(4-pentenyl)pyrrolidine
• 英文别名: benzyl (2R)-2-pent-4-enylpyrrolidine-1-carboxylate
• CAS: 218914-64-8
• 化学式: C₁₇H₂₃NO₂
• 分子量: 273.375
• InChiKey: GROZWXGHFRMGOM-MRXNPFEDSA-N

物化性质

• 沸点：
  381.193±21.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.050±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-N-benzyloxycarbonyl-2-(4-pentenyl)pyrrolidine 在 palladium dihydroxide 吡啶 、 原乙酸三甲酯 、 4-二甲氨基吡啶 、 10% Cd/Pd 、 copper(l) iodide 、 乙酰溴 、 AD-mix-β 、 ammonium acetate 、 氢气 、 4-甲基苯磺酸吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 74.5h， 生成 (5R,8aR)-5-hexyloctahydroindolizine
  参考文献：
  名称：

  New synthesis of all the four stereoisomers of indolizidine 209D and their affinity for nicotinic acetylcholine receptor

  摘要：

  Both enantiomers of a 2-(4-pentenyl)pyrrolidine derivative 4 (65-90% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 2, underwent a second AD to provide all of the four stereoisomers of indolizidine 209D 1 with enantiomeric enhancement (92-98% ee). The affinity of 1 for nicotinic acetylcholine receptor was evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00338-3
• 作为产物：
  描述：

  ((R)-4-Hydroxy-non-8-enyl)-carbamic acid benzyl ester 在 吡啶 、 4-二甲氨基吡啶 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 17.0h， 生成 (R)-N-benzyloxycarbonyl-2-(4-pentenyl)pyrrolidine
  参考文献：
  名称：

  New synthesis of all the four stereoisomers of indolizidine 209D and their affinity for nicotinic acetylcholine receptor

  摘要：

  Both enantiomers of a 2-(4-pentenyl)pyrrolidine derivative 4 (65-90% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 2, underwent a second AD to provide all of the four stereoisomers of indolizidine 209D 1 with enantiomeric enhancement (92-98% ee). The affinity of 1 for nicotinic acetylcholine receptor was evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00338-3

文献信息

• The total synthesis of piclavines A1–4 and their biological evaluation
  作者：Hiroki Takahata、Naoki Okamoto

  DOI：10.1016/s0960-894x(00)00341-3

  日期：2000.8

  The total synthesis of piclavines A1, A2, A3, and A4 has been achieved starting from compound 10 with enantiomeric enhancement. Their biological activities (antibacterial, antimicrobacterial, and antiviral activities and inhibition of cell growth) were evaluated. (C) 2000 Elsevier Science Ltd. All rights reserved.
• New synthesis of all the four stereoisomers of indolizidine 209D and their affinity for nicotinic acetylcholine receptor
  作者：Hiroki Takahata、Minoru Kubota、Kozue Ihara、Naoki Okamoto、Takefumi Momose、Nehad Azer、Amira T. Eldefrawi、Mohyee E. Eldefrawi

  DOI：10.1016/s0957-4166(98)00338-3

  日期：1998.9

  Both enantiomers of a 2-(4-pentenyl)pyrrolidine derivative 4 (65-90% ee), prepared via the asymmetric dihydroxylation (AD) of terminal olefin 2, underwent a second AD to provide all of the four stereoisomers of indolizidine 209D 1 with enantiomeric enhancement (92-98% ee). The affinity of 1 for nicotinic acetylcholine receptor was evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.