1-(2-chloro-2-phenylethyl)-piperidine | 249632-04-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 1-(2-chloro-2-phenylethyl)-piperidine
• 英文别名: 1-[(2S)-2-chloro-2-phenylethyl]piperidine
• CAS: 249632-04-0
• 化学式: C₁₃H₁₈ClN
• 分子量: 223.746
• InChiKey: HXHURGCIBJMJDF-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.45
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  3.24
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2-苯乙硫醇 、 1-(2-chloro-2-phenylethyl)-piperidine 在 三乙胺 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.0h， 生成 1-(2-phenethylsulfanyl-2-phenylethyl)-piperidine
  参考文献：
  名称：

  The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate

  摘要：

  Here we describe a one-pot synthesis of a series of beta-substituted amines as single enantiomers from an initial regioisomeric mixture of styrene oxide ring-opening products. We also report the isolation and characterization of a key beta-chloro intermediate and provide additional insight into the mechanism of the reported alkylations. These results require that the reaction proceeds through a common aziridinium ion intermediate on two separate occasions in order to account for the observed overall net retention of configuration in proceeding from (S)-styrene oxide to the desired beta-substituted amine products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00243-8
• 作为产物：
  描述：

  哌啶 、 (S)-环氧苯乙烷 在 甲基磺酰氯 、 三乙胺 作用下， 生成 1-(2-chloro-2-phenylethyl)-piperidine
  参考文献：
  名称：

  The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate

  摘要：

  Here we describe a one-pot synthesis of a series of beta-substituted amines as single enantiomers from an initial regioisomeric mixture of styrene oxide ring-opening products. We also report the isolation and characterization of a key beta-chloro intermediate and provide additional insight into the mechanism of the reported alkylations. These results require that the reaction proceeds through a common aziridinium ion intermediate on two separate occasions in order to account for the observed overall net retention of configuration in proceeding from (S)-styrene oxide to the desired beta-substituted amine products. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00243-8

文献信息

• The preparation of β-substituted amines from mixtures of epoxide opening products via a common aziridinium ion intermediate
  作者：Shelby R. Anderson、Joshua T. Ayers、Keith M. DeVries、Fumitaka Ito、Debra Mendenhall、Brian C. Vanderplas

  DOI：10.1016/s0957-4166(99)00243-8

  日期：1999.7

  Here we describe a one-pot synthesis of a series of beta-substituted amines as single enantiomers from an initial regioisomeric mixture of styrene oxide ring-opening products. We also report the isolation and characterization of a key beta-chloro intermediate and provide additional insight into the mechanism of the reported alkylations. These results require that the reaction proceeds through a common aziridinium ion intermediate on two separate occasions in order to account for the observed overall net retention of configuration in proceeding from (S)-styrene oxide to the desired beta-substituted amine products. (C) 1999 Elsevier Science Ltd. All rights reserved.