2-phenylindene ozonide | 109963-98-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 2-phenylindene ozonide
• 英文别名: 4-Phenyl-4,5-dihydro-1H-1,4-epoxido-benzo[d][1,2]dioxepin；9-Phenyl-10,11,12-trioxatricyclo[7.2.1.02,7]dodeca-2,4,6-triene
• CAS: 109963-98-6
• 化学式: C₁₅H₁₂O₃
• 分子量: 240.258
• InChiKey: BGXGDZADLYDGLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-phenyl-2-(2-vinylphenyl)ethanone 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 2-phenylindene ozonide
  参考文献：
  名称：

  Ozonolyses of 1,2-diphenyl- and 2-phenylindene

  摘要：

  Ozonolyses of 1,2-diphenylindene (7), 2-phenylindene (18), and the structurally related acyclic keto olefins 13, 14, 26, and 32 were conducted in MeOH/CH2Cl2 at -70 and 0-degrees-C. The structure of the indenes, 7 and 18, and the reaction temperature, were found to exert an influence on the outcome of the reaction. Ozonolysis of 1,2-diphenylindene (7) at -70-degrees-C proceeded exclusively via the carbonyl oxide intermediate 15 providing the methanol-derived isochroman 9a as the sole isolable product. In contrast, four methanol-derived products, 20-23, were obtained from 2-phenylindene (18) under similar reaction conditions, suggesting that the primary ozonide 25 from 18 undergoes two competing modes of decomposition. Ozonolyses of indenes, 7 and 18, and 0-degrees-C gave mainly the corresponding ozonides, 8 and 19, respectively, while analogous reactions at -70-degrees-C resulted in the predominant formation of the methanol-derived products 9 and 20-23, respectively. The major differences in composition between the ozonolysis product mixtures derived from the acyclic keto olefins 13, 14, 26, and 32 and the appropriate corresponding indenes 7 and 18 suggest that the intermediate carbonyl oxides generated from the former do not make significant contributions to the reaction pathways of the latter.

  DOI：

  10.1021/jo00053a026

文献信息

• Criegee et al., Chemische Berichte, 1955, vol. 88, p. 1878,1888
  作者：Criegee et al.

  DOI：——

  日期：——