[(1R,3S)-3-乙酰基-2,2-二甲基环丙基]乙腈 | 144686-75-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: [(1R,3S)-3-乙酰基-2,2-二甲基环丙基]乙腈
• 英文名称: (1R,3S)-2,2,-dimethyl-3-acetylcyclopropaneacetonitrile
• 英文别名: Cyclopropaneacetonitrile, 3-acetyl-2,2-dimethyl-, (1R-cis)-(9CI)；2-[(1R,3S)-3-acetyl-2,2-dimethylcyclopropyl]acetonitrile
• CAS: 144686-75-9
• 化学式: C₉H₁₃NO
• 分子量: 151.208
• InChiKey: LWICIOXNAKBJDE-SFYZADRCSA-N

物化性质

• 沸点：
  252.9±13.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1R,3S)-2,2-二甲基-3-(2-氧丙基)-环丙烷乙腈 在 chromium(VI) oxide 、 氢氧化钾 、 potassium metaperiodate 、 溴 作用下， 以 甲醇 、 乙醚 、 丙酮 为溶剂， 反应 7.0h， 生成 [(1R,3S)-3-乙酰基-2,2-二甲基环丙基]乙腈
  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.