1'-ethylpropyl (Z)-2-methyl-3-(2-methylpropionyloxy)pent-2-enoate | 137708-18-0

• 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: 1'-ethylpropyl (Z)-2-methyl-3-(2-methylpropionyloxy)pent-2-enoate
• 英文别名: pentan-3-yl (Z)-2-methyl-3-(2-methylpropanoyloxy)pent-2-enoate
• CAS: 137708-18-0
• 化学式: C₁₅H₂₆O₄
• 分子量: 270.369
• InChiKey: VYMWANJYOWVVGK-QBFSEMIESA-N

物化性质

• 沸点：
  332.4±25.0 °C(Predicted)
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19.0
• 可旋转键数：
  7.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1'-ethylpropyl (Z)-2-methyl-3-(2-methylpropionyloxy)pent-2-enoate 在 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 葡萄糖 、 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 生成 (2S,3R) 1'-ethylpropyl 3-hydroxy-2-methylpentanoate
  参考文献：
  名称：

  A synthesis of (−)-sitophilate by utilizing yeast-mediated reduction of an enol ester

  摘要：

  The microbial reduction of 1'-ethylpropy 2-methyl-3-oxopentanoate, a beta-keto ester possessing bulky substituent, as well as the corresponding enol ester was examined. Epimeric mixture of hydroxy ester, containing (2S,3S)-isomer as the major product (92%e.e., 43%d.e.) was obtained via the reduction of enol ester with growing cells of Pichia farinosa IAM 4682 in 63% yield. The resulting-beta-hydroxy ester was converted to (2S,3R)-isomer (88%e.e., 96%d.e.), of which e.e. was further enhanced by the lipase-catalyzed partial hydrolysis of the corresponding chloroacetate to give (-)-sitophilate, (99%e.e.) an aggregation pheromone of Sitophillus granarius L.

  DOI：

  10.1016/s0040-4020(01)89726-x
• 作为产物：
  描述：

  1'-ethylpropyl 3-hydroxy-2-methylpentanoate 在 chromium(VI) oxide 、 sodium hydride 作用下， 生成 1'-ethylpropyl (Z)-2-methyl-3-(2-methylpropionyloxy)pent-2-enoate
  参考文献：
  名称：

  A synthesis of (−)-sitophilate by utilizing yeast-mediated reduction of an enol ester

  摘要：

  The microbial reduction of 1'-ethylpropy 2-methyl-3-oxopentanoate, a beta-keto ester possessing bulky substituent, as well as the corresponding enol ester was examined. Epimeric mixture of hydroxy ester, containing (2S,3S)-isomer as the major product (92%e.e., 43%d.e.) was obtained via the reduction of enol ester with growing cells of Pichia farinosa IAM 4682 in 63% yield. The resulting-beta-hydroxy ester was converted to (2S,3R)-isomer (88%e.e., 96%d.e.), of which e.e. was further enhanced by the lipase-catalyzed partial hydrolysis of the corresponding chloroacetate to give (-)-sitophilate, (99%e.e.) an aggregation pheromone of Sitophillus granarius L.

  DOI：

  10.1016/s0040-4020(01)89726-x