(RS)-1-chloro-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-2-yl acetate | 1407829-94-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (RS)-1-chloro-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-2-yl acetate
• 英文别名: [1-chloro-3-[4-(2-methoxyphenyl)piperazin-1-yl]propan-2-yl] acetate
• CAS: 1407829-94-0
• 化学式: C₁₆H₂₃ClN₂O₃
• 分子量: 326.823
• InChiKey: VFPZUOXBJNFGNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  22.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  42.01
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  1-(2-甲氧苯基)哌嗪 在 吡啶 、 lithium bromide 作用下， 以 水 为溶剂， 生成 (RS)-1-chloro-3-(4-(2-methoxyphenyl)piperazin-1-yl)propan-2-yl acetate
  参考文献：
  名称：

  New chemical and chemo-enzymatic routes for the synthesis of (RS)- and (S)-enciprazine

  摘要：

  The chemo-enzymatic synthesis of racemic and enantiopure (RS)- and (S)-enciprazine 1, a non-benzodiazepine anxiolytic drug, is described herein. The synthesis started from 1-(2-methoxyphenyl) piperazine 3, which was treated with 2-(chloromethyl) oxirane (RS)-4 using lithium bromide to afford a racemic alcohol, 1-chloro-3-(4-(2-methoxyphenyl) piperazin-1-yl) propan-2-ol (RS)-6 in 85% yield. Intermediate (S)-6 was synthesized from racemic alcohol (RS)-6 using Candida rugosa lipase (CRL) with vinyl acetate as the acyl donor. Various reaction parameters such as temperature, time, substrate, enzyme concentration, and the effect of the reaction medium on the conversion and enantiomeric excess for the transesterification of (RS)-6 by CRL were optimized. It was observed that 10 mM of (RS)-6, 50 mg/mL of CRL in 4.0 mL of toluene with vinyl acetate (5.4 mmol) as acyl donor at 30 degrees C gave good conversion (C = 49.4%) and enantiomeric excess (ee(p) = 98.4% and ee(s) = 96%) after 9 h of reaction. Compound (S)-6 is a key intermediate for the synthesis of enantiopure (S)-1. The (RS)- and (S)-enciprazine drug 1 was synthesized by treating (RS)and (S)-6 with 3,4,5-trimethoxyphenol 5 using MeCN as a solvent and K2CO3 as a base. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.08.002