endo-1-methyl-3-phenylindene ozonide | 84847-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: endo-1-methyl-3-phenylindene ozonide
• 英文别名: (1S,8R,9R)-8-methyl-1-phenyl-10,11,12-trioxatricyclo[7.2.1.02,7]dodeca-2,4,6-triene
• CAS: 84847-60-9
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: YQIFBMUISTUWJT-LYRGGWFBSA-N

物化性质

• 熔点：
  127-128 °C(Solv: methanol (67-56-1))
• 沸点：
  361.6±42.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  endo-1-methyl-3-phenylindene ozonide 在 氯化锑(V) 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 exo-1-methyl-3-phenylindene ozonide
  参考文献：
  名称：

  Synthesis, x-ray analysis, and acidolysis of exo- and endo-1-methylindene ozonides

  摘要：

  DOI：

  10.1021/ja00346a051
• 作为产物：
  描述：

  Phenyl-[2-[1-[5-phenyl-5-(trifluoromethyl)-1,2,4-trioxolan-3-yl]ethyl]phenyl]methanone 在 2,2,2-三氟苯乙酮 、 臭氧 、 苯基锂 、 三苯基膦 作用下， 以 乙醚 、 苯 为溶剂， 反应 15.0h， 生成 endo-1-methyl-3-phenylindene ozonide
  参考文献：
  名称：

  Ozonolyses of 1-Alkyl-Substituted 3-Methylindenes. Remarkable Effects of the Substituent Steric Bulk and the Stereochemistry of the Carbonyl Oxide Intermediates on the Efficiency of Ozonide Formation

  摘要：

  Ozonolyses of 3-methyl- and 3-isopropyl-1-methylindenes (1a,b) in ether gave mainly the corresponding oligomers 3a,b, while in the case of 3-phenyl- and 3-tert-butyl-1-methylindenes (1c,d), the corresponding exo-endo mixtures of ozonides 2c,d were obtained in good yield, the exo isomer being the major one. The ozonolyses of two stereoisomeric keto vinyl ethers, (E)-16 and (Z)-16, demonstrated that the stereochemistry of the derived carbonyl oxide 5c exerts a remarkable influence on the course of the reaction. Particularly interesting is the fact that syn-5c having a proper geometry for the concerted cycloaddition provided ozonide 2c in high yield even in the presence of trifluoroacetophenone. The high degree of similarity in the nature and distribution of the products from the ozonolyses of keto olefin (E)-16 and 1-methyl-3-phenylindene (1c) would be consistent with their respective reactions proceeding predominantly through a common carbonyl oxide intermediate syn-5c.

  DOI：

  10.1021/jo980542n

文献信息

• Ozonolysis of a series of 1-substituted indenes. The substituent steric effects on the ozonide exo/endo ratios
  作者：Masahiro Miura、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/ja00322a032

  日期：1984.5

  Ozonolyse d'une serie d'indenes disubstitues (-1,2 et -1,3) et trisubstitues (-1,2,3) dans CCl 4

  Ozonolyse d'une serie d'indenes dissubstitues (-1,2 et -1,3) et trisubstitues (-1,2,3) dans CCl 4
• ¹⁸O-Tracer Studies of Fe(II)-Induced Decomposition of 1,2,4-Trioxolanes (Ozonides) Derived from Cyclopentenes and Indenes. Inner-Sphere Electron Transfer Reduction of the Peroxide Linkage
  作者：Manabu Abe、Tomoyasu Inakazu、Johichi Munakata、Masatomo Nojima

  DOI：10.1021/ja990807v

  日期：1999.7.1

  Fe(II)-induced decomposition of 1,2,4-trioxolanes (ozonides) 1 and 2 is studied in detail. The inner-sphere electron transfer reduction, which is sensitive to steric effects, is proposed to be a reasonable mechanism for the peroxide decomposition, i.e., the selective generation of one of the two possible Fe(III)-complexed oxy radicals. The fate of the oxy radical species is revealed in detail by using

  详细研究了 Fe(II) 诱导的 1,2,4-三氧戊环（臭氧化物）1 和 2 的分解。对空间效应敏感的球内电子转移还原被认为是过氧化物分解的合理机制，即选择性生成两种可能的 Fe(III) 络合氧自由基之一。通过在 18O 标记的臭氧化物 1a 和 2a 的还原中使用 18O 示踪剂研究详细揭示了氧自由基物种的命运，其中醚氧被 18O 原子（18O，77%）标记，并且还通过还原在 H218O (18O, 10%) 存在下。18O 示踪剂研究的结果与 Fe(III) 络合氧自由基物种的区域选择性生成一致。
• McCullough, Kevin J.; Sugimoto, Toshiya; Tanaka, Shogo, Journal of the Chemical Society. Perkin transactions I, 1994, # 6, p. 643 - 652
  作者：McCullough, Kevin J.、Sugimoto, Toshiya、Tanaka, Shogo、Kusabayashi, Shigekazu、Nojima, Masatomo

  DOI：——

  日期：——
• Ozonolysis of 1-methylindenes. Solvent, temperature, and substituent electronic effects on the ozonide exo/endo ratio
  作者：Masahiro Miura、Tomohiro Fujisaka、Masatomo Nojima、Shigekazu Kusabayashi、Kevin J. McCullough

  DOI：10.1021/jo00209a028

  日期：1985.5
• Acidolysis of ozonides. An ab initio study
  作者：Masahiro Miura、Shigeru Nagase、Masatomo Nojima、Shigekazu Kusabayashi

  DOI：10.1021/jo00162a014

  日期：1983.7