2,2-dimethyl-1,3-bis(2-oxopropyl)cyclopropane | 90734-28-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-dimethyl-1,3-bis(2-oxopropyl)cyclopropane
• 英文别名: cis-1,3-bis(2-oxopropyl)-2,2-dimethylcyclopropane；2,2-dimethyl-cis-1,3-di-(2-oxopropyl)cyclopropane；Methyl(1R,3S)-2,2-dimethyl-3-(2-oxopropyl)-cyclopropaneacetate；1-[(1S,3R)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]propan-2-one
• CAS: 90734-28-4
• 化学式: C₁₁H₁₈O₂
• 分子量: 182.263
• InChiKey: NHTPIQPGOSQIGI-AOOOYVTPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-dimethyl-1,3-bis(2-oxopropyl)cyclopropane 以 乙醇 、 水 为溶剂， 反应 72.0h， 生成 (1R,3S)-2,2-dimethyl-3-<(2S)-2-hydroxypropyl>-1-(2-oxopropyl)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-氧丙基)-环丙烷乙腈 在 盐酸 、 sodium hydroxide 、 水 、 双氧水 、 对甲苯磺酸 作用下， 以 甲醇 、 水 、 苯 为溶剂， 反应 9.0h， 生成 2,2-dimethyl-1,3-bis(2-oxopropyl)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

文献信息

• Kula, J.; Sikora, M., Polish Journal of Chemistry, 1994, vol. 68, # 2, p. 269 - 274
  作者：Kula, J.、Sikora, M.

  DOI：——

  日期：——
• Naik, R. H.; Bhat, N. G.; Kulkarni, G. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 12, p. 1209 - 1212
  作者：Naik, R. H.、Bhat, N. G.、Kulkarni, G. H.

  DOI：——

  日期：——
• 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.