N-pent-2'-enyl-(2-(S)-hydroxymethyl)pyrrolidine | 211762-86-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: N-pent-2'-enyl-(2-(S)-hydroxymethyl)pyrrolidine
• 英文别名: [(2S)-1-[(E)-pent-2-enyl]pyrrolidin-2-yl]methanol
• CAS: 211762-86-6
• 化学式: C₁₀H₁₉NO
• 分子量: 169.267
• InChiKey: WBDPYRLQAQHSBK-FSIBCCDJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-pent-2'-enyl-(2-(S)-hydroxymethyl)pyrrolidine 在 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 [(S)-1-(1-Ethyl-allyloxy)-pyrrolidin-2-yl]-methanol
  参考文献：
  名称：

  Studies into the asymmetric Meisenheimer rearrangement

  摘要：

  Oxidation of a variety of N-allyl prolinol derivatives gave amine N-oxides with complete diastereoselectivity. On warming, these amine N-oxides undergo [2,3]-Meisenheimer rearrangement to give O-allyl hydroxylamines, albeit with low diastereoselectivity. Attempts to promote asymmetric N-oxidation of N-allyl tertiary amines with a variety of asymmetric oxidants produced only racemic N-oxides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00191-8
• 作为产物：
  描述：

  N-pent-2-enyl-(L)-proline methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 72.0h， 以64%的产率得到N-pent-2'-enyl-(2-(S)-hydroxymethyl)pyrrolidine
  参考文献：
  名称：

  Studies into the asymmetric Meisenheimer rearrangement

  摘要：

  Oxidation of a variety of N-allyl prolinol derivatives gave amine N-oxides with complete diastereoselectivity. On warming, these amine N-oxides undergo [2,3]-Meisenheimer rearrangement to give O-allyl hydroxylamines, albeit with low diastereoselectivity. Attempts to promote asymmetric N-oxidation of N-allyl tertiary amines with a variety of asymmetric oxidants produced only racemic N-oxides. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00191-8

文献信息

• Studies into the asymmetric Meisenheimer rearrangement
  作者：Jonathan E.H Buston、Iain Coldham、Keith R Mulholland

  DOI：10.1016/s0957-4166(98)00191-8

  日期：1998.6

  Oxidation of a variety of N-allyl prolinol derivatives gave amine N-oxides with complete diastereoselectivity. On warming, these amine N-oxides undergo [2,3]-Meisenheimer rearrangement to give O-allyl hydroxylamines, albeit with low diastereoselectivity. Attempts to promote asymmetric N-oxidation of N-allyl tertiary amines with a variety of asymmetric oxidants produced only racemic N-oxides. (C) 1998 Elsevier Science Ltd. All rights reserved.