(1R,3S)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)cyclopropaneacetamide | 144686-77-1

• 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-(2-methyl-1,3-dioxolan-2-ylmethyl)cyclopropaneacetamide
• 英文别名: 2-[(1R,3S)-2,2-dimethyl-3-[(2-methyl-1,3-dioxolan-2-yl)methyl]cyclopropyl]acetamide
• CAS: 144686-77-1
• 化学式: C₁₂H₂₁NO₃
• 分子量: 227.304
• InChiKey: RBMKLNUHIGZRHT-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  61.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1R,3S)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)cyclopropaneacetamide 在 氢氧化钾 、 苄基三乙基氯化铵 、 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (1R,3S)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)cyclopropanecarbonitrile
  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-氧丙基)-环丙烷乙腈 在 sodium hydroxide 、 双氧水 、 对甲苯磺酸 作用下， 以 水 、 苯 为溶剂， 反应 7.0h， 生成 (1R,3S)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)cyclopropaneacetamide
  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.