N-[4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]acetamide | 134582-17-5

• 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: N-[4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]acetamide
• CAS: 134582-17-5
• 化学式: C₁₁H₁₄ClNO₃
• 分子量: 243.69
• InChiKey: VNMUIOBUKDSTAC-JTQLQIEISA-N

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：

  N-[4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]acetamide 、 异丙胺 生成 (S)-practolol
  参考文献：
  名称：

  酶辅助制备对映体纯的β-肾上腺素能阻滞剂III。旋光氯醇衍生物及其转化

  摘要：

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。

  DOI：

  10.1016/s0957-4166(00)80256-6
• 作为产物：
  描述：

  (RS)-1-chloro-3-(p-nitrophenyloxy)propan-2-ol 在 palladium on activated charcoal 溶剂黄146 作用下， 生成 N-[4-[(2R)-3-chloro-2-hydroxypropoxy]phenyl]acetamide
  参考文献：
  名称：

  酶辅助制备对映体纯的β-肾上腺素能阻滞剂III。旋光氯醇衍生物及其转化

  摘要：

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。

  DOI：

  10.1016/s0957-4166(00)80256-6

文献信息

• Diplogelasinospora grovesii IMI 171018, a new whole cell biocatalyst for the stereoselective reduction of ketones
  作者：José D. Carballeira、Emilio Álvarez、Mercedes Campillo、Leonardo Pardo、José V. Sinisterra

  DOI：10.1016/j.tetasy.2004.01.034

  日期：2004.3

  and showed very high activity and stereoselectivity in the reduction of cyclic ketones. The fungus was selected due to its selectivity towards monocyclic and bicyclic ketones and its easy culture conditions, which allow an easy scale-up. D. grovesii is more active in the reduction of conventional ketones than S. cerevisiae type II (from Sigma) and can work in the presence of high ketone concentrations

  筛选了416株（71细菌菌株，45放线菌，59酵母，60担子菌，33海洋真菌和148丝状真菌）以寻找在没有氧化酶活性的情况下表现出还原酶活性的微生物。分离出一种新的微生物，Diplogelasinospora grovesii IMI 171018（一种非病原菌菌株），它在还原环酮方面显示出很高的活性和立体选择性。选择该真菌是由于其对单环和双环酮的选择性以及易于培养的条件，从而易于扩大规模。与传统啤酒酵母相比，格罗夫氏杆菌在还原传统酮方面更活跃。II型（来自Sigma），可以在高酮浓度（<60 mM）存在的情况下工作。为了说明作为微生物醇还原酶底物的羰基化合物的空间和电子性质，已应用比较分子场分析（CoMFA）。CoMFA模型具有高度预测性（q 2 = 0.549），可用于解释和预测可被该微生物还原或无法还原的酮的结构。
• 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
• Highly stereoselective reduction of haloketones using three new yeasts: application to the synthesis of (S)-adrenergic β-blockers related to propranolol
  作者：Fernando Martı́nez Lagos、Jose D. Carballeira、Jose L. Bermúdez、Emilio Alvarez、Jose V. Sinisterra

  DOI：10.1016/j.tetasy.2004.01.024

  日期：2004.3

  The stereoselective reduction of aryloxy-halo-2-propanones 1 or of 1-chloro-3(phthalimdyl)-propan-2-one 2 using baker's yeast usually displays poor yields and/or ees. Three new yeasts, Saccharomyces bayanus CECT 1317, Yarrowia lipolytica CECT 1240 and Pichia mexicana CECT 1015, were selected after a taxonomical screening looking for microorganisms active in the reduction of ketones. These strains have been used for the highly stereoselective reduction of 1 and 2. This reduction is the key step in the stereoselective synthesis of (S)-adrenergic beta-blockers related to the propranolol structure. P. mexicana (reduction of 1) and S. bayanus (the reduction of 2), gave ees greater than 90%, and yields higher than 85% for the (R)-or (S)-halohydrins, respectively. This process constitutes an efficient alternative to the resolution of halohydrins carried out using lipases and can easily be scaled up. (C) 2004 Elsevier Ltd. All rights reserved.
• Enzyme assisted preparation of enantiomerically pure β-adrenergic blockers III. Optically active chlorohydrin derivatives and their conversion
  作者：Ulrich Ader、Manfred P. Schneider

  DOI：10.1016/s0957-4166(00)80256-6

  日期：1992.4

  Optical active chlorohydrin derivatives 2a-m and 3a-m of both enantiomeric series were prepared via both enzymatic hydrolyses and acyltransfer reactions catalysed by a highly selective lipase from Pseudomonas sp.. The resulting building blocks were further transformed into the corresponding β-blockers of high enantiomeric purity.

  两个对映体系列的光学活性氯代醇衍生物2a-m和3a-m是通过酶水解和由假单胞菌属物种的高度选择性脂肪酶催化的酰基转移反应制备的。。将得到的结构单元进一步转化为高对映体纯度的相应β-受体阻滞剂。