(+)-1-(3-chloro-phenyl)-2-propanol

• 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: (+)-1-(3-chloro-phenyl)-2-propanol
• 英文别名: 1-(3-chlorophenyl)propan-2-ol；(2S)-1-(3-chlorophenyl)propan-2-ol
• 化学式: C₉H₁₁ClO
• 分子量: 170.639
• InChiKey: FTKJAJSPPQCNKZ-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  maleic acid (+)-1-(3-chloro-phenyl)-2-propyl monoester 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.02h， 生成 (+)-1-(3-chloro-phenyl)-2-propanol
  参考文献：
  名称：

  Kinetic and chemical resolution of different 1-phenyl-2-propanol derivatives

  摘要：

  Seven chiral target molecules containing a hydroxy group have been resolved by both biocatalytic and chemical means. The lipase-catalyzed acylation mainly yielded the acylated derivative of the (R)-alcohols with moderate enantiomeric excess and the enantiopure (S)-alcohols. In the course of the chemical resolution, first the dicarboxylic acid monoesters of the target molecules were synthesized and the resolution of these monoesters was attempted by different homochiral bases. By re-resolution and/or optimization of the reaction time and/or recrystallization, respectively, each molecule was produced in very high enantiomeric purity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.07.019

文献信息

• Asymmetric Hydrogenation of Ketones and Enones with Chiral Lewis Base Derived Frustrated Lewis Pairs
  作者：Bochao Gao、Xiangqing Feng、Wei Meng、Haifeng Du

  DOI：10.1002/anie.201914568

  日期：2020.3.9

  The concept of frustrated Lewis pairs (FLPs) has been widely applied in various research areas, and metal-free hydrogenation undoubtedly belongs to the most significant and successful ones. In the past decade, great efforts have been devoted to the synthesis of chiral boron Lewis acids. In a sharp contrast, chiral Lewis base derived FLPs have rarely been disclosed for the asymmetric hydrogenation.

  沮丧的路易斯对（FLP）概念已在各个研究领域中得到广泛应用，无金属氢化无疑是最重要和最成功的氢化方法。在过去的十年中，人们一直致力于合成手性硼路易斯酸。与之形成鲜明对比的是，极少有人公开了手性路易斯碱衍生的FLP用于不对称氢化。在这项工作中，通过手性恶唑啉路易斯碱与非手性硼路易斯酸的简单结合，开发了一种新型的手性FLP，从而为未来手性FLP的发展提供了有希望的新方向。这些手性FLP被证明对酮，烯酮和色酮的不对称氢化非常有效，从而以高达95％ee的高收率提供了相应的产品。