Chloro-acetic acid 2-benzo[1,3]dioxol-5-yl-1-methyl-ethyl ester | 521098-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: Chloro-acetic acid 2-benzo[1,3]dioxol-5-yl-1-methyl-ethyl ester
• 英文别名: 1-(2H-1,3-Benzodioxol-5-yl)propan-2-yl chloroacetate；1-(1,3-benzodioxol-5-yl)propan-2-yl 2-chloroacetate
• CAS: 521098-02-2
• 化学式: C₁₂H₁₃ClO₄
• 分子量: 256.686
• InChiKey: PDYPUMFSYOYKLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  alpha-甲基-1,3-苯并二氧代-5-乙醇 、 氯乙酸 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到Chloro-acetic acid 2-benzo[1,3]dioxol-5-yl-1-methyl-ethyl ester
  参考文献：
  名称：

  Amano PS-catalysed enantioselective acylation of (±)-α-methyl-1,3-benzodioxole-5-ethanol: an efficient resolution of chiral intermediates of the remarkable antiepileptic drug candidate, (−)-talampanel

  摘要：

  (S)-(+)-alpha-Methyl-1,3-benzodioxole-5-ethanoI 5 is a chiral building block in the synthesis of the future drug (-)-talam-panel 1. Amano PS-induced enantioselective acylation of (+/-)-3 at 50degreesC using vinyl acetate as acyl donor furnished (+)-5 in 53% yield and 80% e.e., and the corresponding acetyl derivative (-)-(R)-alpha-methyl-1,3-benzodioxole-5-ethyl acetate 6 in 44% yield and 96% e.e. The base-catalysed methanolysis of (-)-6 followed by Mitsunobu inversion and subsequent methanolysis of the product, (+)-8 also gave the desired (+)-5 in 38% overall yield (four steps) and 96% e.e. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(02)00836-4

文献信息

• Amano PS-catalysed enantioselective acylation of (±)-α-methyl-1,3-benzodioxole-5-ethanol: an efficient resolution of chiral intermediates of the remarkable antiepileptic drug candidate, (−)-talampanel
  作者：Srinivasan Easwar、Narshinha P. Argade

  DOI：10.1016/s0957-4166(02)00836-4

  日期：2003.2

  (S)-(+)-alpha-Methyl-1,3-benzodioxole-5-ethanoI 5 is a chiral building block in the synthesis of the future drug (-)-talam-panel 1. Amano PS-induced enantioselective acylation of (+/-)-3 at 50degreesC using vinyl acetate as acyl donor furnished (+)-5 in 53% yield and 80% e.e., and the corresponding acetyl derivative (-)-(R)-alpha-methyl-1,3-benzodioxole-5-ethyl acetate 6 in 44% yield and 96% e.e. The base-catalysed methanolysis of (-)-6 followed by Mitsunobu inversion and subsequent methanolysis of the product, (+)-8 also gave the desired (+)-5 in 38% overall yield (four steps) and 96% e.e. (C) 2003 Elsevier Science Ltd. All rights reserved.