(5S)-allyl-1-(2-hydroxy-(1'R)-phenylethyl)-pyrrolidin-2-one | 132959-50-3

• 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: (5S)-allyl-1-(2-hydroxy-(1'R)-phenylethyl)-pyrrolidin-2-one
• 英文别名: N-[2-(2R-phenyl ethanol)]-5S-propenyl-2-pyrrolidinone；(5S)-1-[(1R)-2-hydroxy-1-phenylethyl]-5-prop-2-enylpyrrolidin-2-one
• CAS: 132959-50-3
• 化学式: C₁₅H₁₉NO₂
• 分子量: 245.321
• InChiKey: HEBONCBHVCESRX-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5S)-allyl-1-(2-hydroxy-(1'R)-phenylethyl)-pyrrolidin-2-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 ammonium formate 作用下， 以 甲醇 为溶剂， 反应 19.0h， 生成 (+)-(R)-2-丙基吡咯烷
  参考文献：
  名称：

  A simple asymmetric synthesis of 2-substituted pyrrolidines from 3-acylpropionic acids

  摘要：

  The title compounds have been prepared from 3-acylpropionic acids 2 and (-)-R-phenylglycinol in a three-step sequence in > 98% enantiomeric excess. The R group in 2 ultimately becomes the 2-substituent in the chiral pyrrolidine.

  DOI：

  10.1021/jo00007a011
• 作为产物：
  描述：

  (R)-(+)-N-(1-phenyl-2-hydroxyethyl)succinimide 在 sodium tetrahydroborate 、 四氯化钛 、 三氟乙酸 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 (5S)-allyl-1-(2-hydroxy-(1'R)-phenylethyl)-pyrrolidin-2-one
  参考文献：
  名称：

  Expedient syntheses of indolizidines (−)-167B and (−)-209D

  摘要：

  Indolizidine alkaloids (+/-)-167B and (-)-209D were synthesized via an expedient route using hydroacylation and amination. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(01)00369-x

文献信息

• Asymmetric synthesis of 5-substituted pyrrolidinones via a chiral N-acyliminium equivalent
  作者：Isabelle Baussanne、Angèle Chiaroni、Jacques Royer

  DOI：10.1016/s0957-4166(01)00195-1

  日期：2001.5

  5-Substituted pyrrolidinones 5 were synthesized in good yields and with fair to good diastereoselectivities from the chiral non-racemic oxazolopyrrolidinone 4. Various nucleophiles including cuprates, silanes and phosphites were used. The chiral induction is thought to arise from a chelated N-acyliminium species. (C) 2001 Elsevier Science Ltd. All rights reserved.
• MEYERS, A. I.;BURGESS, LAURENCE E., J. ORG. CHEM., 56,(1991) N, C. 2294-2296
  作者：MEYERS, A. I.、BURGESS, LAURENCE E.

  DOI：——

  日期：——
• A simple asymmetric synthesis of 2-substituted pyrrolidines from 3-acylpropionic acids
  作者：A. I. Meyers、Laurence E. Burgess

  DOI：10.1021/jo00007a011

  日期：1991.3

  The title compounds have been prepared from 3-acylpropionic acids 2 and (-)-R-phenylglycinol in a three-step sequence in > 98% enantiomeric excess. The R group in 2 ultimately becomes the 2-substituent in the chiral pyrrolidine.
• Expedient syntheses of indolizidines (−)-167B and (−)-209D
  作者：Guncheol Kim、Eun-ju Lee

  DOI：10.1016/s0957-4166(01)00369-x

  日期：2001.8

  Indolizidine alkaloids (+/-)-167B and (-)-209D were synthesized via an expedient route using hydroacylation and amination. (C) 2001 Published by Elsevier Science Ltd.