1-phenyl-6,7,8-trioxa-bicyclo<3.2.1>octane | 23253-31-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三氧戊环
• 英文名称: 1-phenyl-6,7,8-trioxa-bicyclo<3.2.1>octane
• 英文别名: 1-phenyl-6,7,8-trioxabicyclo<3.2.1>octane；1-phenylcyclopentene ozonide；(1S,5S)-1-phenyl-6,7,8-trioxabicyclo[3.2.1]octane
• CAS: 23253-31-8
• 化学式: C₁₁H₁₂O₃
• 分子量: 192.214
• InChiKey: AIJQQAYDNHMZAD-QWRGUYRKSA-N

物化性质

• 沸点：
  272.7±39.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-phenyl-6,7,8-trioxa-bicyclo<3.2.1>octane 在 氯磺酸 、 氯化锑(V) 、 双氧水 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 4-苯甲酰基丁酸甲酯
  参考文献：
  名称：

  Miura, Masahiro; Nojima, Masatomo; Kusabayashi, Shigekazu, Journal of the Chemical Society. Perkin transactions I, 1980, p. 2909 - 2913

  摘要：

  DOI：
• 作为产物：
  描述：

  1-苯基环戊烯 在 臭氧 作用下， 以 二氯甲烷 为溶剂， 生成 1-phenyl-6,7,8-trioxa-bicyclo<3.2.1>octane
  参考文献：
  名称：

  A Convenient and Efficient Workup of Ozonolysis Reactions Using Triethylamine

  摘要：

  Comparison were made between triethylamine and methyl sulfide for their use as a quenching agent in the ozonolysis of a variety of alkenes. The reactions involving triethylamine often gave better yields and proceeded faster than those of involving methyl sulfide. The role of triethylamine played as base instead of reducing agent in the reaction.

  DOI：

  10.1080/00397919308011249

文献信息

• The mechanistic study and synthetic applications of the base treatment in the ozonolytic reactions
  作者：Yung-Son Hon、Sheng-Wun Lin、Ling Lu、Yao-Jung Chen

  DOI：10.1016/0040-4020(95)98699-i

  日期：1995.4

  E1cb mechanism is the overwhelming process in the reaction of bases and ozonides. As a quenching agent in the ozonolysis of a variety of alkenes, the reactions involving triethylamine often gave better yields and proceeded faster than those involving methyl sulfide. On the other hand, in the presence of 4 Å molecular sieves, the secondary amines reacted with mono- and 1,1-di-substituted ozonides to afford

  E1cb机制是碱和臭氧化物反应中的压倒性过程。作为各种烯烃的臭氧分解反应的淬灭剂，涉及三乙胺的反应通常比涉及甲基硫醚的反应收率更高，并且进行速度更快。另一方面，在4Å分子筛的存在下，仲胺与单和1,1-二取代的臭氧化物反应，以高收率提供还原性胺化产物。反应混合物中甲酸铵的形成也支持了臭氧化物与胺反应中的E1cb机理。
• Unprecedented formation of a cyclic tetramer from the acidolysis of indene ozonide. Isolation and characterisation of a novel dodecaoxacycloicosane derivative
  作者：Kevin J. McCullough、Koichi Teshima、Masatomo Nojima

  DOI：10.1039/c39930000931

  日期：——

  Treatment of indene ozonide with chlorosulfonic acid in methylene chloride at 0 °C affords a crystalline tetramer of the ozonide, the structure of which is shown by X-ray crystallographic analysis to contain a novel 20-membered dodecaoxacycloicosane ring system.

  在0℃下，用氯磺酸在二氯甲烷中用氯磺酸处理吲哚酮氧化物，得到该酮氧化物的结晶四聚体，其结构通过X射线晶体学分析显示为包含新颖的20元十二碳环二十四烷环体系。
• Miura, Masahiro; Nojima, Masatomo; Kusabayashi, Shigekazu, Journal of the Chemical Society. Perkin transactions I, 1980, p. 2909 - 2913
  作者：Miura, Masahiro、Nojima, Masatomo、Kusabayashi, Shigekazu

  DOI：——

  日期：——
• A Convenient and Efficient Workup of Ozonolysis Reactions Using Triethylamine
  作者：Yung-Son Hon、Sheng-Wun Lin、Yao-Jung Chen

  DOI：10.1080/00397919308011249

  日期：1993.6

  Comparison were made between triethylamine and methyl sulfide for their use as a quenching agent in the ozonolysis of a variety of alkenes. The reactions involving triethylamine often gave better yields and proceeded faster than those of involving methyl sulfide. The role of triethylamine played as base instead of reducing agent in the reaction.