Ethyl (2S,3S)-3-chloro-2-hydroxyhexanoate | 113524-87-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Ethyl (2S,3S)-3-chloro-2-hydroxyhexanoate
• 英文别名: Ethyl (2S,3R)-3-chloro-2-hydroxyhexanoate；Ethyl (2R,3S)-3-chloro-2-hydroxyhexanoate
• CAS: 113524-87-1；113524-94-0
• 化学式: C₈H₁₅ClO₃
• 分子量: 194.658
• InChiKey: MXSAEAFBEPKWPE-BQBZGAKWSA-N

物化性质

• 沸点：
  261.2±20.0 °C(predicted)
• 密度：
  1.120±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  12.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  Ethyl 3-chloro-2-oxohexanoate 在 磷酸二氢铵 、 potassium dihydrogenphosphate 、 葡萄糖 、 magnesium sulfate 、 calcium carbonate 作用下， 以 水 为溶剂， 反应 65.5h， 生成 Ethyl (2S,3R)-3-chloro-2-hydroxyhexanoate 、 Ethyl (2S,3S)-3-chloro-2-hydroxyhexanoate 、 ethyl (2R,3R)-3-chloro-2-hydroxyhexanoate 、 Ethyl (2S,3S)-3-chloro-2-hydroxyhexanoate
  参考文献：
  名称：

  Highly enantioselective reduction of 3-chloro-2-oxoalkanoates with fermenting bakers' yeast. A new synthesis of optically active 3-chloro-2-hydroxyalkanoates and glycidic esters

  摘要：

  Reduction of 3-chloro-2-oxoalkanoic esters with fermenting bakers' yeast gave optically active 3-chloro-2-hydroxyalkanoic esters 2 (anti(2S,3R)/syn (2S,3S) = 52:48-90:10) in 50-85% yields with >95% ee except for 43% ee of ethy syn-(2S,3S)-3-chloro-2-hydroxy-4 phenylbutanoate (2j). Compounds 2 were treated with NaOEt to give (E)-(2R,3S)-2,3-epoxyalkanoates 3 in 30-66% yields with 44-64% ee. Optically active 2,3-epoxy alcohols (cis-23, trans-23, and trans-25), key intermediates for the syntheses of (-)-disparlure (4), mosquito pheromone (5), and a component of passion fruit flavor (6), were prepared with more than 86% ee in high yields.

  DOI：

  10.1021/jo00054a036