(R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol | 147220-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
• 英文别名: [(2R)-3-(4-chlorophenoxy)-2-hydroxypropyl] acetate
• CAS: 147220-31-3
• 化学式: C₁₁H₁₃ClO₄
• 分子量: 244.675
• InChiKey: WUGNBSZDBSVFHW-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  3-p-chlorophenoxy-2-hydroxypropyl ethanoate 在 baker's yeast 、 草酰氯 、 sodium phosphate buffer 、 二甲基亚砜 、 三乙胺 、 蔗糖 作用下， 反应 2.83h， 生成 (R)-1-acetoxy-3-(4-chlorophenoxy)propan-2-ol
  参考文献：
  名称：

  Baker's yeast mediated stereoselective biotransformation of 1-acetoxy-3-aryloxypropan-2-ones

  摘要：

  A series of 1-acetoxy-3-aryloxypropan-2-ones la-m were synthesized and subjected to biotransformation by baker's yeast yielding optically active monoacetates 5 or ent-5 and/or diols 4 of moderate to excellent enantiomeric purity. The dependence of the reduction/hydrolysis ratio and stereoselectivity on the size and substitution pattern of the aromatic moiety in the substrate is also discussed. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00626-5

文献信息

• Exploration of the expeditious potential of<i>Pseudomonas fluorescens</i>lipase in the kinetic resolution of racemic intermediates and its validation through molecular docking
  作者：Surbhi Soni、Bharat P. Dwivedee、Vishnu K. Sharma、Gopal Patel、Uttam C. Banerjee

  DOI：10.1002/chir.22771

  日期：2018.1

  for the two racemic alcohols, respectively. Docking of the R‐ and S‐enantiomers of the intermediates demonstrated stronger H‐bond interaction between the hydroxyl group of the R‐enantiomer and the key binding residues of the catalytic site of the lipase, while the S‐enantiomer demonstrated lesser interaction. Thus, docking study complemented the experimental outcome that PFL preferentially acylated the

  对于（合成的深刻时间有效的化学酶促方法小号）- 3-（4-氯苯氧基）丙-1,2-二醇和（小号）- 1-氯-3-（2,5-二氯苯氧基）丙-2-使用荧光假单胞菌成功开发了两种重要的药物中间体-ol脂肪酶（PFL）。使用乙酸乙烯酯作为酰化剂，甲苯/己烷作为溶剂，反应温度为30°C，成功实现了动力学拆分，从而实现了高对映选择性和转化率。在最佳条件下，PFL表现出50.2％的转化率，95.0％的对映体过量，在1小时的最佳时间内对映选择性（E = 153）和50.3％的转化率，95.2％的对映体过量，在最佳时间内的对映选择性（E = 161）两种外消旋醇分别需要3小时。所述的对接R-和小号证实羟基的之间更强的氢键相互作用的中间体的对映异构体[R -对映体和键结合脂肪酶的催化位点的残基，而小号对映体的相互作用较小。因此，对接研究补充了PFL优先酰化中间体R形式的实验结果。本研究证明了一种经济有效的快速生
• Kinetic resolution of aliphatic 1,2-diols by a lipase-catalyzed sequential acetylation
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1016/s0040-4039(00)60573-7

  日期：1993.1

  The kinetic resolution of 13 racemic aliphatic 1,2-diols (rac-1a-m) by means of a lipase-catalyzed sequential acetylation was investigated. The enantioselectivity of the 3-aryloxy-propane-1,2-diols rac-1a-k depends on the substitution pattern at the aryl ring.
• Kinetic resolution of acyclic 1,2-diols using a sequential lipase-catalyzed transesterification in organic solvents
  作者：Fritz Theil、Judith Weidner、Sibylle Ballschuh、Annamarie Kunath、Hans Schick

  DOI：10.1021/jo00081a018

  日期：1994.1

  A method for the kinetic resolution of 3-(aryloxy)-1,2-propanediols rac-1a-n without additional protection-deprotection steps using a lipase-catalyzed sequential transesterification with lipase amnno PS has been developed. In the first step of this one-pot procedure the racemic 1,2-diols are acylated regioselectively at the primary hydroxy group without enantioselection. The subsequent acylation at the secondary hydroxy group of the formed primary monoacetate is responsible for high enantioselection. The enantioselectivity of this transformation depends significantly on the substitution pattern of the aryl ring and the organic solvent used. 3-(Aryloxy)-1,2-propanediols with substituents in the para-position show a much higher enantioselectivity than the corresponding derivatives with ortho-substituents. Among other substrates, the pharmaceuticals Mephenesin, Guaifenesin, and Chlorphenesin have been resolved. The replacement of the aryloxy by alkyl substituent causes a dramatic decrease of enantioselectivity.