11-Hydroxyundecanoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 11-Hydroxyundecanoate
• 化学式: C₁₁H₂₁O₃
• 分子量: 201.286
• InChiKey: KNRCBASNXNXUQQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  60.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  羟基十一烷酸内酯 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 0.42h， 生成 11-Hydroxyundecanoate
  参考文献：
  名称：

  Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. Strain energies and conformations

  摘要：

  The enthalpies of hydrolysis of the monocyclic lactones from gamma-butyrolactone to tridecanolactone were determined calorimetrically, and the acyclic ethyl esters having the same number of atoms were studied in the same fashion. The enthalpies of reduction of the lactones to the corresponding alpha,omega-alkanediols with lithium triethylborohydride also were determined. The enthalpies of formation of the lactones and the ethyl esters were derived from these data. They were converted to values for the gas phase by measuring the enthalpies of vaporization of ethyl esters and of lactones. In the cases of gamma-butyrolactone and delta-valerolactone, the enthalpies of formation were in good accord with the previously reported values determined via combustion calorimetry. The strain energies of the lactones were obtained via isodesmic reactions. Valerolactone had a strain energy of 11 kcal/mol, and the largest strain energy was found with octanolactone (13 kcal/mol). The conformations of gamma-butyrolactone and delta-valerolactone were studied via MP2/6-31G* geometry optimizations, and the conformations of the other lactones were studied with use of the molecular mechanics program MM3. The energies of the lactones estimated via molecular mechanics were compared with the experimental results.

  DOI：

  10.1021/ja00020a036

文献信息

• Lactones. 2. Enthalpies of hydrolysis, reduction, and formation of the C4-C13 monocyclic lactones. Strain energies and conformations
  作者：Kenneth B. Wiberg、Roy F. Waldron

  DOI：10.1021/ja00020a036

  日期：1991.9

  The enthalpies of hydrolysis of the monocyclic lactones from gamma-butyrolactone to tridecanolactone were determined calorimetrically, and the acyclic ethyl esters having the same number of atoms were studied in the same fashion. The enthalpies of reduction of the lactones to the corresponding alpha,omega-alkanediols with lithium triethylborohydride also were determined. The enthalpies of formation of the lactones and the ethyl esters were derived from these data. They were converted to values for the gas phase by measuring the enthalpies of vaporization of ethyl esters and of lactones. In the cases of gamma-butyrolactone and delta-valerolactone, the enthalpies of formation were in good accord with the previously reported values determined via combustion calorimetry. The strain energies of the lactones were obtained via isodesmic reactions. Valerolactone had a strain energy of 11 kcal/mol, and the largest strain energy was found with octanolactone (13 kcal/mol). The conformations of gamma-butyrolactone and delta-valerolactone were studied via MP2/6-31G* geometry optimizations, and the conformations of the other lactones were studied with use of the molecular mechanics program MM3. The energies of the lactones estimated via molecular mechanics were compared with the experimental results.