rac-1-(3,5-difluorophenyl)-2-acetoxypropan-1-one | 376346-56-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rac-1-(3,5-difluorophenyl)-2-acetoxypropan-1-one
• 英文别名: [1-(3,5-Difluorophenyl)-1-oxopropan-2-yl] acetate
• CAS: 376346-56-4
• 化学式: C₁₁H₁₀F₂O₃
• 分子量: 228.195
• InChiKey: ANWXHTXKFMQGLG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  rac-1-(3,5-difluorophenyl)-2-acetoxypropan-1-one 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 生成 1-(3,5-difluorophenyl)-2-hydroxypropan-1-one
  参考文献：
  名称：

  Simple chemoenzymatic access to enantiopure pharmacologically interesting (R)-2-hydroxypropiophenones

  摘要：

  A chemoenzymatic synthesis of pharmacological interesting (R)-2-hydroxypropiophenones starting from propiophenone derivatives is described. Manganese(III) acetate-mediated acetoxylation followed by fungus-mediated hydrolysis of propiophenone derivatives affords (R)-2-hydroxypropiophenones in high enantiomeric excess. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00346-9
• 作为产物：
  描述：

  Acetic acid (S)-2-(3,5-difluoro-phenyl)-1-methyl-2-oxo-ethyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 24.0h， 生成 rac-1-(3,5-difluorophenyl)-2-acetoxypropan-1-one
  参考文献：
  名称：

  Simple chemoenzymatic access to enantiopure pharmacologically interesting (R)-2-hydroxypropiophenones

  摘要：

  A chemoenzymatic synthesis of pharmacological interesting (R)-2-hydroxypropiophenones starting from propiophenone derivatives is described. Manganese(III) acetate-mediated acetoxylation followed by fungus-mediated hydrolysis of propiophenone derivatives affords (R)-2-hydroxypropiophenones in high enantiomeric excess. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00346-9

文献信息

• Biocatalytic racemization of synthetically important functionalized α-hydroxyketones using microbial cells
  作者：Bettina M. Nestl、Anne Bodlenner、Rainer Stuermer、Bernhard Hauer、Wolfgang Kroutil、Kurt Faber

  DOI：10.1016/j.tetasy.2007.06.005

  日期：2007.7

  Biocatalytic racemization of straight-chain and cyclic acyloins bearing (halo)alkyl, alkenyl and functionalized (hetero)aryl moieties was accomplished using whole resting cells of bacteria, fungi and yeasts. Mild physiological reaction conditions ensured the suppression of undesired side-reactions, such as elimination or condensation. This biocatalytic protocol represents a useful tool for the clean racemization of unwanted enantiomers of synthetically important alpha-hydroxyketones derived from kinetic resolution. (c) 2007 Elsevier Ltd. All rights reserved.