(1S,2R)-1-苯基-2-(1-吡咯烷基)-1-丙醇 | 1215194-05-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (1S,2R)-1-苯基-2-(1-吡咯烷基)-1-丙醇
• 英文名称: (1S,2R)-(+)-1-phenyl-2-(1-pyrrolidinyl)-1-propanol hydrochloride
• 英文别名: (1S,2R)-1-Phenyl-2-(1-pyrrolidinyl)-1-propanol hydrochloride；(1S,2R)-1-phenyl-2-pyrrolidin-1-ylpropan-1-ol;hydrochloride
• CAS: 1215194-05-0
• 化学式: C₁₃H₁₉NO*ClH
• 分子量: 241.761
• InChiKey: PMKBLGNPWCWAAH-LOCPCMAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  23.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-苯基-2-(1-吡咯烷基)-1-丙醇 在 sodium dichromate 、 硫酸 、 sodium hydroxide 、 盐酸 作用下， 以 水 、 甲苯 为溶剂， 反应 12.33h， 以84%的产率得到(R)-(+)-1-phenyl-2-(1-pyrrolidinyl)-1-propanone hydrochloride
  参考文献：
  名称：

  Chiral α-alkylation/arylation in 1-phenyl-2-(1-pyrrolidinyl)-1-propanol through Grignard reactions

  摘要：

  Complete asymmetric induction has been achieved during Grignard alkylations/arylations resulting in (1S,2R)- and (1R,2R)-1-phenyl-1-alkyl/aryl-2-(1-pyrrolidinyl)-1-propanols which are isolated as hydrochlorides. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.11.019
• 作为产物：
  描述：

  (1S,2R)-(+)-1-phenyl-2-(1-piperidinyl)-1-propanol hydrochloride 在 氯化亚砜 、 水 、 N,N-二甲基甲酰胺 、 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 反应 14.0h， 生成 (1S,2R)-1-苯基-2-(1-吡咯烷基)-1-丙醇
  参考文献：
  名称：

  Remarkable enantioselective α-amination in 1-phenyl-2-(n-alkylamino)-1-propanol

  摘要：

  Abstract(1R,2R)‐1‐Phenyl‐1‐alkyl/arylamino‐2‐(N‐alkylamino)propane hydrochloride salts have been synthesized with high degree of enantiomeric purity from (1S,2R)‐(+)‐1‐phenyl‐2‐(N‐alkylamino)‐1‐propanol through the corresponding chloro derivatives. This reaction sequence involves three inversions with overall inversion of configuration at C‐1. Chirality, 2012. © 2012 Wiley Periodicals, Inc.

  DOI：

  10.1002/chir.21996

文献信息

• Chiral α-alkylation/arylation in 1-phenyl-2-(1-pyrrolidinyl)-1-propanol through Grignard reactions
  作者：Borkatte N. Hitesh Kumar、Velayudham Murugesan、Tangirala Prakasam、Pathangi S. Srinivasan、Devalla V. Ramana

  DOI：10.1016/j.tetasy.2009.11.019

  日期：2009.12

  Complete asymmetric induction has been achieved during Grignard alkylations/arylations resulting in (1S,2R)- and (1R,2R)-1-phenyl-1-alkyl/aryl-2-(1-pyrrolidinyl)-1-propanols which are isolated as hydrochlorides. (C) 2009 Elsevier Ltd. All rights reserved.
• Remarkable enantioselective α-amination in 1-phenyl-2-(n-alkylamino)-1-propanol
  作者：Borkatte N. Hitesh Kumar、Velayutham Murugesan、Tangirala Prakasam、Pathangi S. Srinivasan、Devalla V. Ramana

  DOI：10.1002/chir.21996

  日期：2012.3

  Abstract(1R,2R)‐1‐Phenyl‐1‐alkyl/arylamino‐2‐(N‐alkylamino)propane hydrochloride salts have been synthesized with high degree of enantiomeric purity from (1S,2R)‐(+)‐1‐phenyl‐2‐(N‐alkylamino)‐1‐propanol through the corresponding chloro derivatives. This reaction sequence involves three inversions with overall inversion of configuration at C‐1. Chirality, 2012. © 2012 Wiley Periodicals, Inc.