methyl 3-(2-hydroxy-1-methyl-5-oxocyclopentyl)propanoate | 38694-79-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: methyl 3-(2-hydroxy-1-methyl-5-oxocyclopentyl)propanoate
• CAS: 38694-79-0
• 化学式: C₁₀H₁₆O₄
• 分子量: 200.235
• InChiKey: XJEAVZGYZVYNCH-UHFFFAOYSA-N

物化性质

• 沸点：
  302.0±27.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  63.6
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-<2-(methoxycarbonyl)ethyl>-2-methyl-1,3-cyclopentanedione 在 sodium tetrahydroborate 作用下， 以 乙二醇二甲醚 为溶剂， 生成 methyl 3-(2-hydroxy-1-methyl-5-oxocyclopentyl)propanoate 、
  参考文献：
  名称：

  Comparative reductive desymmetrization of 2,2-disubstituted-cycloalkane-1,3-diones

  摘要：

  Reductive desymmetrization of 2-methyl-2-substituted-cycloalkane-1,3-diones can be effected using either NaBH(4) in DME or lithium tri-tert-butoxyaluminum hydride (LTBA) in THF at -60 degrees C. The former is a new approach that offers slightly greater diastereoselectivity in the reduction of 2,2-disubstituted-cyclopentane- 1,3-diones while LTBA is superior with 2,2-disubstituted-cyclohexane- 1,3-diones. Both conditions minimize subsequent reduction to diols thereby furnishing high yields of 1,3-ketols. Particularly rapid monoreductions are observed with 2-methyl-2-nitroethylcyclopentane-1,3-dione and 2-cyanoethyl-2-methylcyclopentane-1,3-dione when treated with NaBH(4) in DME at -60 degrees C. As expected, diastereoselectivity varies considerably with the substitution at C-2. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.065