5-methyl-2-(3-methyl-4-pentenyl)-6-heptenoic acid | 879491-85-7

• 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: 5-methyl-2-(3-methyl-4-pentenyl)-6-heptenoic acid
• 英文别名: 5-methyl-2-(3-methylpent-4-enyl)hept-6-enoic acid
• CAS: 879491-85-7
• 化学式: C₁₄H₂₄O₂
• 分子量: 224.343
• InChiKey: YTTDRGCGJGKGNI-UHFFFAOYSA-N

物化性质

• 沸点：
  318.4±11.0 °C(Predicted)
• 密度：
  0.913±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.89
• 重原子数：
  16.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  5-methyl-2-(3-methyl-4-pentenyl)-6-heptenoic acid 在 bis[1,1-di(trifluoromethyl)ethoxy][(2,6-diisopropylphenyl)imino](2-methyl-2-phenylpropylidene)molybdenum 吡啶 、 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 生成 (E)-3,6,9,12,15,18-Hexamethyl-icosa-1,10,19-triene
  参考文献：
  名称：

  Understanding the effect of allylic methyls in olefin cross-metathesis

  摘要：

  A series of NMR spectroscopy experiments have been conducted with both the model compound, 3-methyl-1-pentene and the corresponding ADMET monomer 3,6,9-trimethylundeca-1,10-diene (11) to better understand the effect of allylic methyls during olefin metathesis chemistry. Traditional ADMET catalysts such as Schrock's molybdenum (1), and Grubbs' ruthenium 1st and 2nd generation (2 and 3) were examined under cross-metathesis and ADMET conditions. Regardless of catalyst selection, 50% or less metathesis conversion was observed for all reactions, especially in the case of the more sterically encumbered diene. With Schrock's molybdenum catalyst 1, the reaction leads to an accumulation of the non-productive metallacyclobutane, trapping the catalyst in an inactive form. With Grubbs' ruthenium catalysts 2 and 3, the substrate coordinates to the metal center primarily to yield non-productive metathesis, which results in a build-up of the methylidene complex leading to catalyst decomposition. These results are directly correlated to the orientation of the substrate's bulk during the metallacyclobutane formation, the alkyl branch being adjacent to the metal center in the case of the molybdenum catalyst 1, and opposite to it in the case of ruthenium catalyst 2 and 3. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.09.030
• 作为产物：
  描述：

  diethyl 2,2-bis-(3-methyl-4-pentenyl)malonate 在 氢氧化钾 作用下， 以 乙醇 、 水 、 萘烷 为溶剂， 反应 3.0h， 生成 5-methyl-2-(3-methyl-4-pentenyl)-6-heptenoic acid
  参考文献：
  名称：

  Understanding the effect of allylic methyls in olefin cross-metathesis

  摘要：

  A series of NMR spectroscopy experiments have been conducted with both the model compound, 3-methyl-1-pentene and the corresponding ADMET monomer 3,6,9-trimethylundeca-1,10-diene (11) to better understand the effect of allylic methyls during olefin metathesis chemistry. Traditional ADMET catalysts such as Schrock's molybdenum (1), and Grubbs' ruthenium 1st and 2nd generation (2 and 3) were examined under cross-metathesis and ADMET conditions. Regardless of catalyst selection, 50% or less metathesis conversion was observed for all reactions, especially in the case of the more sterically encumbered diene. With Schrock's molybdenum catalyst 1, the reaction leads to an accumulation of the non-productive metallacyclobutane, trapping the catalyst in an inactive form. With Grubbs' ruthenium catalysts 2 and 3, the substrate coordinates to the metal center primarily to yield non-productive metathesis, which results in a build-up of the methylidene complex leading to catalyst decomposition. These results are directly correlated to the orientation of the substrate's bulk during the metallacyclobutane formation, the alkyl branch being adjacent to the metal center in the case of the molybdenum catalyst 1, and opposite to it in the case of ruthenium catalyst 2 and 3. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2005.09.030