(S)-(-)-1-benzoyloxy-3-chloropropan-2-ol

• 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: (S)-(-)-1-benzoyloxy-3-chloropropan-2-ol
• 英文别名: (S)-3-chloro-2-hydroxypropyl benzoate；[(2S)-3-chloro-2-hydroxypropyl] benzoate
• 化学式: C₁₀H₁₁ClO₃
• 分子量: 214.649
• InChiKey: SOEGKTCFKODFPT-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯-2-氧代丙基苯甲酸酯 在 baker's yeast 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 3.0h， 生成 (S)-(-)-1-benzoyloxy-3-chloropropan-2-ol 、 (R)-(+)-1-benzoyloxy-3-chloropropan-2-ol
  参考文献：
  名称：

  Chemo-enzymatic synthesis of levodropropizine

  摘要：

  Levodropropizine, an antitussive drug, was prepared in high enantiomeric excess in three steps, starting from dichloroacetone (2). Monosubstitution of 2 with sodium benzoate and subsequent baker's yeast reduction stereoselectively afforded the corresponding chlorohydrin in 73% ee, which was converted to levodropropizine and enantiomerically enriched up to 95% ee by fractional crystallisation.

  DOI：

  10.1016/s0014-827x(03)00189-7

文献信息

• Synthesis of optically active 2-hydroxy monoesters via-kinetic resolution and asymmetric cyclization catalyzed by heterometallic chiral (salen) Co complex
  作者：Wenji Li、Santosh Singh Thakur、Shu-Wei Chen、Chang-Kyo Shin、Rahul B. Kawthekar、Geon-Joong Kim

  DOI：10.1016/j.tetlet.2006.03.042

  日期：2006.5

  The binuclear chiral (salen) Co complexes bearing Lewis acids of Al and Ga catalyze regio- and enantioselective ring opening of terminal epoxides with carboxylic acids. The ring opened product of epichlorohydrin with carboxylic acids followed by cyclization step in the presence of catalyst and base represent straightforward, efficient methods for the synthesis of enatiomerically enriched (>99% ee)

  带有Al和Ga的路易斯酸的双核手性（salen）Co配合物用羧酸催化末端环氧化物的区域和对映选择性开环。表氯醇与羧酸的开环产物，然后在催化剂和碱的存在下进行环化步骤，是合成对映体富集（> 99％ee）有价值的末端环氧化物的直接，有效的方法。在催化过程中，Co-Al和Co-Ga的不同路易斯酸具有很强的协同作用。
• Chemo-enzymatic synthesis of levodropropizine
  作者：Emilia Caselli、Giovanni Tosi、Arrigo Forni、Maria Bucciarelli、Fabio Prati

  DOI：10.1016/s0014-827x(03)00189-7

  日期：2003.10

  Levodropropizine, an antitussive drug, was prepared in high enantiomeric excess in three steps, starting from dichloroacetone (2). Monosubstitution of 2 with sodium benzoate and subsequent baker's yeast reduction stereoselectively afforded the corresponding chlorohydrin in 73% ee, which was converted to levodropropizine and enantiomerically enriched up to 95% ee by fractional crystallisation.