2-oxabicyclo<2.2.2>octane-1-carboxylic acid | 36269-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxabicyclo<2.2.2>octane-1-carboxylic acid
• 英文别名: 2-Oxobicyclo<2.2.2>octan-1-carbonsaeure；Bicyclo-<2.2.2>-octan-2-on-1-carbonsaeure；2-Oxobicyclo[2.2.2]octane-1-carboxylic acid
• CAS: 36269-54-2
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: LXKRZEQZSXYIFF-UHFFFAOYSA-N

物化性质

• 沸点：
  333.6±25.0 °C(Predicted)
• 密度：
  1.330±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  methyl 2-oxobicyclo<2.2.2>octane-1-carboxylate 生成 2-oxabicyclo<2.2.2>octane-1-carboxylic acid
  参考文献：
  名称：

  Evidence for intramolecular electrostatic catalysis as a possible mechanism in the hydrolysis of vinyl ethers in aqueous solution

  摘要：

  The hydrolysis of the vinyl ether functional group in 2-methoxybicyclo[2.2.2]oct-2-ene-1-carboxylic acid (2) has been found to be catalyzed by intramolecular electrostatic catalysis by the carboxylate ion of the substrate.1 The rate constant ratios of the charged and the neutral form of the substrate are 32.3 and 31.2 for catalysis by hydronium ion and acetic acid, respectively. This is in contrast to ratios that have been found for vinyl ethers hydrolyzed by intramolecular general-acid catalysis, where large rate ratios for catalysis by hydronium ion but small rate ratios, normally a factor 2, when catalyzed by acetic acid are observed. The solvent isotope effect, 3.4 +/- 0.5, is close to what has been predicted for electrostatic catalysis in the hydrolysis of prostacyclin (1).

  DOI：

  10.1021/jo00001a047

文献信息

• Intramolecular electrostatic catalysis in the hydrolysis of a bicyclic vinyl ether
  作者：Torbj�rn Halvarsson、Nils-�ke Bergman

  DOI：10.1039/c39890001219

  日期：——

  Intramolecular electrostatic catalysis by a carboxylate ion has been observed in the hydrolysis of 2-methoxybicyclo[2.2.2]oct-2-ene-1-carboxylic acid in aqueous buffer solutions.

  在含水缓冲溶液中2-甲氧基双环[2.2.2]辛-2-烯-1-羧酸的水解中，观察到了羧酸根离子对分子内静电的催化作用。
• Evidence for intramolecular electrostatic catalysis as a possible mechanism in the hydrolysis of vinyl ethers in aqueous solution
  作者：Torbjoern Halvarsson、Nils Aake Bergman

  DOI：10.1021/jo00001a047

  日期：1991.1

  The hydrolysis of the vinyl ether functional group in 2-methoxybicyclo[2.2.2]oct-2-ene-1-carboxylic acid (2) has been found to be catalyzed by intramolecular electrostatic catalysis by the carboxylate ion of the substrate.1 The rate constant ratios of the charged and the neutral form of the substrate are 32.3 and 31.2 for catalysis by hydronium ion and acetic acid, respectively. This is in contrast to ratios that have been found for vinyl ethers hydrolyzed by intramolecular general-acid catalysis, where large rate ratios for catalysis by hydronium ion but small rate ratios, normally a factor 2, when catalyzed by acetic acid are observed. The solvent isotope effect, 3.4 +/- 0.5, is close to what has been predicted for electrostatic catalysis in the hydrolysis of prostacyclin (1).