(1R,3S)-2,2,-dimethyl-<(2R)-hydroxypropyl>-1-propylcyclopropane | 144732-94-5

• 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-<(2R)-hydroxypropyl>-1-propylcyclopropane
• CAS: 144732-94-5
• 化学式: C₁₁H₂₂O
• 分子量: 170.295
• InChiKey: BLCTYDSBEIMYMI-BBBLOLIVSA-N

反应信息

• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 生成 (1R,3S)-2,2,-dimethyl-<(2S)-hydroxypropyl>-1-propylcyclopropane 、 (1R,3S)-2,2,-dimethyl-<(2R)-hydroxypropyl>-1-propylcyclopropane
  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