Acetic acid 1-chloromethyl-2-[4-(2-methoxy-ethyl)-phenoxy]-ethyl ester | 1017859-19-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: Acetic acid 1-chloromethyl-2-[4-(2-methoxy-ethyl)-phenoxy]-ethyl ester
• CAS: 1017859-19-6
• 化学式: C₁₄H₁₉ClO₄
• 分子量: 286.755
• InChiKey: ZAFCWZAXLIOSST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.42
• 重原子数：
  19.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  Acetic acid 1-chloromethyl-2-[4-(2-methoxy-ethyl)-phenoxy]-ethyl ester 生成
  参考文献：
  名称：

  A new application of Candida antarctica lipase for obtaining natural homochiral BBAs aryloxypropanolamine

  摘要：

  CAL offers increased ee,together with broad substrate structural tolerance that makes it a firm candidate for the resolution of BBAs of type 1. Copyright (C) 1996 Published by Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00313-8
• 作为产物：
  描述：

  乙酸乙烯酯 、 1-氯-3-[4-(2-甲氧基乙基)苯氧基]-2-丙醇 在 Novozym 435 作用下， 以 正己烷 、 丙酮 为溶剂， 反应 28.0h， 生成 Acetic acid 1-chloromethyl-2-[4-(2-methoxy-ethyl)-phenoxy]-ethyl ester
  参考文献：
  名称：

  Chemoenzymatic synthesis of the potential antihypertensive agent (2R,2′S)-β-hydroxyhomometoprolol

  摘要：

  The kinetic resolution of 1-chloro-3-[4-(2-methoxyetliyl)phenoxy]-2-propanol rac-4 with Novozym 435 and vinyl stearate, a key step in the gram-scale synthesis of (2S)-2-[[(2R)-2-hydroxy-3-[4-(2-methoxyethyl)phenoxy] propyl]amino]-1-butanol (R,S)-1 a potent antihypertensive agent currently under investigation, is reported here. Our approach differs from the previously reported synthesis, which involves a tedious and poorly effective fractional crystallization of (R,S)-1. This novel approach incorporates an enzymatic resolution for the efficient preparation of the oxirane precursor (R)-3. The two main advantages arising from this strategy are the high enantioselectivity of the enzymatic process and the facilitated recovery of the hydrophobic stearate intermediate (S)-5. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.11.003