1-chloro-3-(2,5-dimethyl-phenyloxy)propan-2-one | 689260-89-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-chloro-3-(2,5-dimethyl-phenyloxy)propan-2-one
• 英文别名: 1-Chloro-3-(2,5-dimethylphenoxy)propan-2-one
• CAS: 689260-89-7
• 化学式: C₁₁H₁₃ClO₂
• 分子量: 212.676
• InChiKey: PCOBJUNAWVYJQP-UHFFFAOYSA-N

物化性质

• 沸点：
  308.7±32.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-chloro-3-(2,5-dimethyl-phenyloxy)propan-2-one 在 sodium phosphate buffer 、 Yarrowia lipolytica CECT 1240 resting cells 、 蔗糖 作用下， 以 苯 为溶剂， 反应 48.0h， 以90%的产率得到(S)-(+)-1-chloro-3-(2,5-dimethyl-phenyloxy)propan-2-ol
  参考文献：
  名称：

  Highly stereoselective reduction of haloketones using three new yeasts: application to the synthesis of (S)-adrenergic β-blockers related to propranolol

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.01.024
• 作为产物：
  描述：

  (RS)-1-chloro-3-(2,5-dimethyl-phenyloxy)propan-2-ol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以63%的产率得到1-chloro-3-(2,5-dimethyl-phenyloxy)propan-2-one
  参考文献：
  名称：

  Highly stereoselective reduction of haloketones using three new yeasts: application to the synthesis of (S)-adrenergic β-blockers related to propranolol

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2004.01.024

文献信息

• 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.