1'-ethylpropyl-2-methyl-3-oxopentanoate | 137708-17-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 1'-ethylpropyl-2-methyl-3-oxopentanoate
• 英文别名: 1-ethylpropyl 2-methyl-3-oxopentanoate；Pentanoic acid, 2-methyl-3-oxo-, 1-ethylpropyl ester；pentan-3-yl 2-methyl-3-oxopentanoate
• CAS: 137708-17-9
• 化学式: C₁₁H₂₀O₃
• 分子量: 200.278
• InChiKey: DJCMPWRFELDGPU-UHFFFAOYSA-N

物化性质

• 沸点：
  235.1±8.0 °C(Predicted)
• 密度：
  0.947±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• 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：

  1'-ethylpropyl-2-methyl-3-oxopentanoate 在 dipotassium hydrogenphosphate 、 potassium dihydrogenphosphate 、 葡萄糖 、 sodium hydride 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 反应 16.0h， 生成 (2S, 3R)-1-ethylpropyl 3-(3,5-dinitrobenzoyloxy)-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 作用下， 以81%的产率得到1'-ethylpropyl-2-methyl-3-oxopentanoate
  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

文献信息

• Reductive biotransformation of carbonyl compounds—application of fungus, Geotrichum sp. G38 in organic synthesis
  作者：Gu Jian-Xin、Li Zu-Yi、Lin Guo-Qiang

  DOI：10.1016/s0040-4020(01)87947-3

  日期：1993.6

  The microbial transformation of 2- and 3-oxo esters and diketones with Geotrichum sp. G38 and its application to the syntheses of the key intermediates of several bioactive compounds such as (R)-denopamine 8, (R)-fluoxetine 11 and (2S, 3R)-sitophilate 14 were described.

  Geotrichum sp对2-和3-氧代酯和二酮的微生物转化。描述了G38及其在几种生物活性化合物如（R）-地巴胺8，（R）-氟西汀11和（2S，3R）-sitophilate 14的关键中间体的合成中的应用。
• Stereoselective chemoenzymatic synthesis of sitophilate: a natural pheromone
  作者：Dimitris Kalaitzakis、Spiros Kambourakis、David J. Rozzell、Ioulia Smonou

  DOI：10.1016/j.tetasy.2007.10.008

  日期：2007.10

  The aggregation pheromone of the granary weevil Sitophilus granarius, (2S,3R)-1-ethylpropyl 3-hydroxy-2-methylpentanoate, has been synthesized in 63% total isolated yield and high chemical and enantiomeric purity (98% de, > 99% ee) from readily available methyl 3-oxopentanoate. A stereoselective ketone reduction followed by an ester hydrolysis, were the two key steps of the synthesis and were both performed by commercially available enzymes. (c) 2007 Elsevier Ltd. All rights reserved.