(1R,3S)-2,2-dimethyl-3-<(2S)-2-hydroxypropyl>-1-(2-hydroxyethyl)cyclopropane | 144732-96-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,3S)-2,2-dimethyl-3-<(2S)-2-hydroxypropyl>-1-(2-hydroxyethyl)cyclopropane
• 英文别名: (2S)-1-[(1S,3R)-3-(2-hydroxyethyl)-2,2-dimethylcyclopropyl]propan-2-ol
• CAS: 144732-96-7
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: GQYOHACDWKLTMF-YIZRAAEISA-N

物化性质

• 沸点：
  253.6±8.0 °C(predicted)
• 密度：
  0.964±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl 2,2-dimethyl-3-(2,2-ethylenedioxypropyl)cyclopropane-cis-1-acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 73.5h， 生成 (1R,3S)-2,2-dimethyl-3-<(2S)-2-hydroxypropyl>-1-(2-hydroxyethyl)cyclopropane
  参考文献：
  名称：

  Baker's yeast-induced asymmetric reduction of the keto group activated by the cyclopropane unit.

  摘要：

  Certain cis-3-substituted 2,2-dimethyl-1-(2-oxopropyl)-cyclopropanes are effectively reduced by baker's yeast to give predominantly (s)-isomers of the corresponding 2-hydroxypropyl derivatives. Reduction of the 2-oxopropyl group proceeds more rapidly (ca. 3.5 times) and with higher stereoselectivity [(S):(R) = 98:2] when the group is attached to the (s)-carbon of the cyclopropane unit than of the keto group attached to the (R)-carbon [(S):(R) = (88):(12)]. Yeast reduction of the keto derivatives is effectively carried out when substituents at C-3 are as follows: CH2COOCH3, -CH2COCH3, -CN, -CH2CN, -CH2CH2OH, and the relative rates of reduction are 36:36:15:13:7. No reduction occurs when substituents at C-3 are propyl, 2-methyl-2-hydroxypropyl or 2-methyl-1,3-dioxolan-2-yl methyl groups.

  DOI：

  10.1016/s0957-4166(00)82103-5