methyl (1R,3S)-2,2-dimethyl-3-<(2S)-2-hydroxypropyl>cyclopropaneacetate | 144686-73-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl (1R,3S)-2,2-dimethyl-3-<(2S)-2-hydroxypropyl>cyclopropaneacetate
• 英文别名: methyl 2-[(1R,3S)-3-[(2S)-2-hydroxypropyl]-2,2-dimethylcyclopropyl]acetate
• CAS: 144686-73-7
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: LQODOYDTUGCWHS-XHNCKOQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1R,3S)-2,2-dimethyl-3-<(2S)-2-hydroxypropyl>cyclopropaneacetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以77%的产率得到(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
• 作为产物：
  描述：

  (1R,3S)-2,2-二甲基-3-(2-氧代丙基)-环丙烷乙酸甲酯 以 乙醇 、 水 为溶剂， 反应 72.0h， 生成 methyl (1R,3S)-2,2-dimethyl-3-<(2S)-2-hydroxypropyl>cyclopropaneacetate
  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

文献信息

• Baker's yeast-induced asymmetric reduction of the keto group activated by the cyclopropane unit.
  作者：Alexey V. Tkachev、Alexey V. Rukavishnikov、Yuri V. Gatilov、Irina Yu. Bagrjanskaja

  DOI：10.1016/s0957-4166(00)82103-5

  日期：1992.9

  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.