methyl 2,2-dimethyl-3-(2,2-ethylenedioxypropyl)cyclopropane-cis-1-acetate | 76449-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,2-dimethyl-3-(2,2-ethylenedioxypropyl)cyclopropane-cis-1-acetate
• 英文别名: methyl (1R,3S)-2,2,-dimethyl-3-propyl-1-(2-methyl-1,3-dioxolan-2-ylmethyl)cyclopropaneacetate；methyl 2-[(1R,3S)-2,2-dimethyl-3-[(2-methyl-1,3-dioxolan-2-yl)methyl]cyclopropyl]acetate
• CAS: 76449-63-3
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: XWKPKPGDVCPRKE-ZJUUUORDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2,2-dimethyl-3-(2,2-ethylenedioxypropyl)cyclopropane-cis-1-acetate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以71%的产率得到(-)-2-<(1R,3S)-2,2-Dimethyl-3-(2-oxopropyl)cyclopropyl>ethanol
  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 、 乙二醇 在 吡啶盐酸盐 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 methyl 2,2-dimethyl-3-(2,2-ethylenedioxypropyl)cyclopropane-cis-1-acetate
  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

• Bhat, N. G.; Joshi, G. D.; Gore, K. G., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1981, vol. 20, # 7, p. 558 - 561
  作者：Bhat, N. G.、Joshi, G. D.、Gore, K. G.、Kulkarni, G. H.、Mitra, R. B.

  DOI：——

  日期：——
• Mane, B. M.; Gore, K. G.; Kulkarni, G. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1980, vol. 19, # 7, p. 605 - 607
  作者：Mane, B. M.、Gore, K. 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.