(RS)-1-chloro-3-(p-acetamidophenyloxy)-2-propanol | 28763-60-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (RS)-1-chloro-3-(p-acetamidophenyloxy)-2-propanol
• 英文别名: 4'-(3-Chlor-2-hydroxy-propoxy)acetanilid；N-[4-(3-chloro-2-hydroxypropoxy)phenyl]acetamide
• CAS: 28763-60-2
• 化学式: C₁₁H₁₄ClNO₃
• 分子量: 243.69
• InChiKey: VNMUIOBUKDSTAC-UHFFFAOYSA-N

物化性质

• 沸点：
  484.3±35.0 °C(Predicted)
• 密度：
  1.290±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  58.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (RS)-1-chloro-3-(p-acetamidophenyloxy)-2-propanol 在 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以95%的产率得到1-chloro-3-(p-acetamidophenyloxy)-2-propanone
  参考文献：
  名称：

  Preparation of halohydrin β-blocker precursors using yeast-catalysed reduction

  摘要：

  The preparation of halohydrin beta -blocker precursors using yeast-catalysed reduction of alpha -haloketones was performed. The influence in the yield and e.e, of several process variables was analysed. The (S)-enantioselectivity observed with Saccharomyces cerevisiae can be changed to (R)-enantioselectivity using methyl vinyl ketone as selective inhibitor (25 mM). Using resting fresh cells better yields and e.e.s are observed than using growing cells. Yarrowia lipolytica 1240 resting cells gave 87% yield of (S)-1-chloro-3(1-naphthyloxy)propan-2-ol (99% e.e.). Pichia mexicana 11105 resting cells gave 85% yield of (R)-1-chloro-3(1-naphthyloxy)propan-2-ol (precursor of propranolol) (95% e.e). The reduction process is applied to other alpha -haloketones, a lower e.e, being obtained the closer the size of the ketone substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00425-0
• 作为产物：
  描述：

  对乙酰氨基酚 、 环氧氯丙烷 在 吡啶 、 盐酸 作用下， 以 氯仿 为溶剂， 反应 25.0h， 以90%的产率得到(RS)-1-chloro-3-(p-acetamidophenyloxy)-2-propanol
  参考文献：
  名称：

  Preparation of halohydrin β-blocker precursors using yeast-catalysed reduction

  摘要：

  The preparation of halohydrin beta -blocker precursors using yeast-catalysed reduction of alpha -haloketones was performed. The influence in the yield and e.e, of several process variables was analysed. The (S)-enantioselectivity observed with Saccharomyces cerevisiae can be changed to (R)-enantioselectivity using methyl vinyl ketone as selective inhibitor (25 mM). Using resting fresh cells better yields and e.e.s are observed than using growing cells. Yarrowia lipolytica 1240 resting cells gave 87% yield of (S)-1-chloro-3(1-naphthyloxy)propan-2-ol (99% e.e.). Pichia mexicana 11105 resting cells gave 85% yield of (R)-1-chloro-3(1-naphthyloxy)propan-2-ol (precursor of propranolol) (95% e.e). The reduction process is applied to other alpha -haloketones, a lower e.e, being obtained the closer the size of the ketone substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00425-0

文献信息

• A new application of Candida antarctica lipase for obtaining natural homochiral BBAs aryloxypropanolamine
  作者：Jose L. Bermudez、Carmen del Campo、Loreto Salazar、Emilio F. Llama、Jose V. Sinisterra

  DOI：10.1016/0957-4166(96)00313-8

  日期：1996.9

  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
• Preparation of halohydrin β-blocker precursors using yeast-catalysed reduction
  作者：Fernando Martı́nez、Carmen Del Campo、J.V Sinisterra、Emilio F Llama

  DOI：10.1016/s0957-4166(00)00425-0

  日期：2000.12

  The preparation of halohydrin beta -blocker precursors using yeast-catalysed reduction of alpha -haloketones was performed. The influence in the yield and e.e, of several process variables was analysed. The (S)-enantioselectivity observed with Saccharomyces cerevisiae can be changed to (R)-enantioselectivity using methyl vinyl ketone as selective inhibitor (25 mM). Using resting fresh cells better yields and e.e.s are observed than using growing cells. Yarrowia lipolytica 1240 resting cells gave 87% yield of (S)-1-chloro-3(1-naphthyloxy)propan-2-ol (99% e.e.). Pichia mexicana 11105 resting cells gave 85% yield of (R)-1-chloro-3(1-naphthyloxy)propan-2-ol (precursor of propranolol) (95% e.e). The reduction process is applied to other alpha -haloketones, a lower e.e, being obtained the closer the size of the ketone substituents. (C) 2001 Elsevier Science Ltd. All rights reserved.