methyl (1S,3R)-2,2-dimethyl-3-(2-oxopropyl)cyclopropaneacetate | 144733-02-8

• 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 (1S,3R)-2,2-dimethyl-3-(2-oxopropyl)cyclopropaneacetate
• 英文别名: methyl [(1S,3R)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]acetate；methyl 2-[(1S,3R)-2,2-dimethyl-3-(2-oxopropyl)cyclopropyl]acetate
• CAS: 144733-02-8
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: MGHKLYIYPFGGDY-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (1S,3R)-2,2-dimethyl-3-(2-oxopropyl)cyclopropaneacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以80%的产率得到(1S,5R)-2-(1-hydroxyethylidene)-6,6-dimethylbicyclo[3.1.0]hexan-3-one
  参考文献：
  名称：

  衍生自（+）-3-carene的吡唑; 新型有效的选择性鞘氨醇-1-磷酸（S1P 1）受体激动剂的支架

  摘要：

  高通量筛选和领先的优化导致“ carene”被鉴定为显示选择性S1P 1受体激动作用的有前途的支架。在这项工作的同时，我们建立了S1P 1受体的药效团模型，突出了有效受体激动作用所需的最低结构要求。

  DOI：

  10.1016/j.bmcl.2009.11.045
• 作为产物：
  描述：

  重氮甲烷 、 (1S,3R)-2,2-dimethyl-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-1-<(2RS)-2-hydroxypropyl>cyclopropane 在 sodium hypobromide 作用下， 生成 methyl (1S,3R)-2,2-dimethyl-3-(2-oxopropyl)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

• Pyrazole derived from (+)-3-carene; a novel potent, selective scaffold for sphingosine-1-phosphate (S1P1) receptor agonists
  作者：Frédéric J. Zécri、Rainer Albert、Gregory Landrum、Klaus Hinterding、Nigel G. Cooke、Danilo Guerini、Markus Streiff、Christian Bruns、Barbara Nuesslein-Hildesheim

  DOI：10.1016/j.bmcl.2009.11.045

  日期：2010.1

  High throughput screening and hit to lead optimization led to the identification of ‘carene’ as a promising scaffold showing selective S1P1 receptor agonism. In parallel to this work we have established a pharmacophore model for the S1P1 receptor highlighting the minimal structural requirement necessary for potent receptor agonism.

  高通量筛选和领先的优化导致“ carene”被鉴定为显示选择性S1P 1受体激动作用的有前途的支架。在这项工作的同时，我们建立了S1P 1受体的药效团模型，突出了有效受体激动作用所需的最低结构要求。
• 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.