exo-2-(benzoyloxy)-6,7,8-trioxabicyclo<3.2.1>octane | 137919-22-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: exo-2-(benzoyloxy)-6,7,8-trioxabicyclo<3.2.1>octane
• 英文别名: [(1S,2R,5R)-6,7,8-trioxabicyclo[3.2.1]octan-2-yl] benzoate
• CAS: 137919-22-3；137919-23-4
• 化学式: C₁₂H₁₂O₅
• 分子量: 236.224
• InChiKey: VUOYYDHRUZHNCL-FOGDFJRCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-环戊烯-1-基苯甲酸酯 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 endo-2-(benzoyloxy)-6,7,8-trioxabicyclo<3.2.1>octane 、 exo-2-(benzoyloxy)-6,7,8-trioxabicyclo<3.2.1>octane
  参考文献：
  名称：

  The influence of remote heteroatom substituents on the stereoselectivity of cyclopentene ozonolysis

  摘要：

  The stereoselectivity for ozonide formation from cyclopentenes with allylic heteroatom substituents has been examined. Silyl ethers give high selectivity in favor of the exo-substituted ozonide, while esters of 2-cyclopentenol form ozonide mixtures with little stereoselection. Trapping experiments establish that fragmentation of the primary ozonides is highly regioselective to give only one of the isomeric omega-oxo carbonyl oxide intermediates and that the variation in final ozonide stereochemistry results from differing interactions between the remote substituent groups and the carbonyl oxide system during cyclization of this intermediate. The effect of substituent and solvent on ozonide stereochemistry suggests a dominant role for electrostatic repulsion between carbonyl oxide and the heteroatom substituent during intramolecular cycloaddition. A chair-like transition state is proposed for this process and is in accord with the increase in exo selectivity for derivatives of 2-methyl-2-cyclopentenol.

  DOI：

  10.1021/jo00028a059

文献信息

• The influence of remote heteroatom substituents on the stereoselectivity of cyclopentene ozonolysis
  作者：William H. Bunnelle、Terry A. Isbell

  DOI：10.1021/jo00028a059

  日期：1992.1

  The stereoselectivity for ozonide formation from cyclopentenes with allylic heteroatom substituents has been examined. Silyl ethers give high selectivity in favor of the exo-substituted ozonide, while esters of 2-cyclopentenol form ozonide mixtures with little stereoselection. Trapping experiments establish that fragmentation of the primary ozonides is highly regioselective to give only one of the isomeric omega-oxo carbonyl oxide intermediates and that the variation in final ozonide stereochemistry results from differing interactions between the remote substituent groups and the carbonyl oxide system during cyclization of this intermediate. The effect of substituent and solvent on ozonide stereochemistry suggests a dominant role for electrostatic repulsion between carbonyl oxide and the heteroatom substituent during intramolecular cycloaddition. A chair-like transition state is proposed for this process and is in accord with the increase in exo selectivity for derivatives of 2-methyl-2-cyclopentenol.