ethyl 4-methylheptanoate

• 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: ethyl 4-methylheptanoate
• 英文别名: (S)-ethyl 4-methylheptanoate；(+)(S)-3-methyl-hexane-carboxylic acid-(1)-ethyl ester；(+)(S)-3-Methyl-hexan-carbonsaeure-(1)-aethylester；ethyl (4S)-4-methylheptanoate
• 化学式: C₁₀H₂₀O₂
• 分子量: 172.268
• InChiKey: NYSADWJQUICPEE-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  12
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲基碘化镁 、 乙醚 、 ethyl 4-methylheptanoate 生成 (+)(S)-2.5-dimethyl-octane
  参考文献：
  名称：

  Levene; Marker, Journal of Biological Chemistry, 1932, vol. 95, p. 15

  摘要：

  DOI：
• 作为产物：
  描述：

  (R)-citronellyl tosylate 在 sodium periodate 、 dilithium tetrachlorocuprate 、 rhodium(III) chloride hydrate 、 potassium carbonate 作用下， 以 四氢呋喃 、 四氯化碳 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 77.0h， 生成 ethyl 4-methylheptanoate
  参考文献：
  名称：

  Pheromone synthesis. Part 258. Synthesis of the enantiomers of the beetle pheromones ethyl 4-methylheptanoate, 4-methyloctanoic acid and 4-methyl-1-nonanol, and HPLC analysis of their derivatives to determine their enantiomeric purities

  摘要：

  The enantiomers of citronella) have been converted into the enantiomers of the following beetle Pheromones: ethyl 4-methylheptanoate (produced by male Nicrophorus vespilloides), 4-methyloctanoic acid (produced by male Oryctes elegans), and 4-methyl-1-nonanol (produced by female Tenebrio molitor). The enantiomeric purities of the synthetic pheromones were determined by HPLC analysis of the corresponding acids after derivatization with Ohrui's reagent [(S)-1-(anthracene-2,3-dicarboximido)-2-propanol]. The enantiomers of 4-methyl-1-nonanol could also be analyzed employing another Ohrui's reagent [(1S,2S)-2-(naphthalene-2,3-dicarboximido)cyclohexane-l-carboxylic acid]. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.01.014

文献信息

• Iridium-Catalyzed Asymmetric Hydrogenation of Unfunctionalized, Trialkyl-Substituted Olefins
  作者：Aie Wang、Rui P. A. Fraga、Esther Hörmann、Andreas Pfaltz

  DOI：10.1002/asia.201000595

  日期：2011.2.1

  Chiral iridium complexes with bicyclic pyridine‐based N,P ligands have emerged as efficient catalysts for the enantioselective hydrogenation of unfunctionalized trialkyl‐substituted olefins. Optimization of the reaction conditions by variation of the solvent, pressure, and temperature led to enantiomeric excesses of up to 99 %. Three pure alkenes, (E)‐2‐cyclohexyl‐2‐butene and (E)‐ and (Z)‐3,4‐dimethyl‐2‐pentene

  具有双环吡啶基N，P配体的手性铱配合物已成为未官能化三烷基取代烯烃对映选择性加氢的有效催化剂。通过改变溶剂，压力和温度来优化反应条件，导致对映体过量高达99％。将（E）-2-环己基-2-丁烯和（E）-和（Z）-3,4-二甲基-2-戊烯这三种纯烯烃分别转化为相应的手性烷烃，分别为97％，94％和93 ％  ee， 分别。醋酸α-和γ-生育三烯基酯的三个C bondsC键的加氢导致醋酸α-和γ-生育酚酯具有非常高的非对映选择性。相同的催化剂已成功用于加氢取代带有γ位羧酸酯或酮基的三取代烯烃。该反应被用作关门菌西双螺旋菌的信息素的高度对映选择性合成中的关键步骤。结构类似的烯丙基醇的氢化也给出了高对映选择性。
• Pheromone synthesis. Part 258. Synthesis of the enantiomers of the beetle pheromones ethyl 4-methylheptanoate, 4-methyloctanoic acid and 4-methyl-1-nonanol, and HPLC analysis of their derivatives to determine their enantiomeric purities
  作者：Kenji Mori、Kazuaki Akasaka

  DOI：10.1016/j.tetasy.2016.01.014

  日期：2016.3

  The enantiomers of citronella) have been converted into the enantiomers of the following beetle Pheromones: ethyl 4-methylheptanoate (produced by male Nicrophorus vespilloides), 4-methyloctanoic acid (produced by male Oryctes elegans), and 4-methyl-1-nonanol (produced by female Tenebrio molitor). The enantiomeric purities of the synthetic pheromones were determined by HPLC analysis of the corresponding acids after derivatization with Ohrui's reagent [(S)-1-(anthracene-2,3-dicarboximido)-2-propanol]. The enantiomers of 4-methyl-1-nonanol could also be analyzed employing another Ohrui's reagent [(1S,2S)-2-(naphthalene-2,3-dicarboximido)cyclohexane-l-carboxylic acid]. (C) 2016 Elsevier Ltd. All rights reserved.
• Levene; Marker, Journal of Biological Chemistry, 1932, vol. 95, p. 15
  作者：Levene、Marker

  DOI：——

  日期：——