1,2-Diphenylacenaphtenoxid | 164411-17-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,2-Diphenylacenaphtenoxid
• CAS: 164411-17-0
• 化学式: C₂₄H₁₆O
• 分子量: 320.39
• InChiKey: VLMKGEVRUDFFLT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.37
• 重原子数：
  25.0
• 可旋转键数：
  2.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  12.53
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1,2-Diphenylacenaphtenoxid 在 氧气 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以48%的产率得到8-Benzoyl-1-naphthylbenzoat
  参考文献：
  名称：

  �bertragung von drei Sauerstoffen auf die olefinische Doppelbindung von 1,2-Diphenylacenaphthen und 1,2-Diphenyl-3,3,4,4-tetramethylcyclobuten

  摘要：

  The olefinic double bond of 1,2-diphenylacenaphthylene (1) is cleaved into its ozonide 2 (respectively into its Baeyer-Villiger rearrangement product 3) via two independent pathways: Pathway A represents the classical ozonolysis (simultaneous three-oxygen transfer) followed by a Baeyer-Villiger rearrangement, pathway B utilizes a two-step three-oxygen transfer; usual epoxidation (mono-oxygen transfer) is followed by C,C homolysis yielding a deep red diradical which shows fast two-oxygen addition (two-oxygen transfer) of molecular oxygen. The labile intermediate ozonide 2 suffers quantitative Baeyer-Villiger rearrangement under reaction conditions necessary to achieve oxirane C,C-cleavage. Therefore, the particularly stable ozonide 11 from 1,2-diphenyl-3,3,4,4-tetramethylcyclobutene (10) is prepared according to pathway B starting from Arnolds's oxirane 12. Both oxidation methods are compared with regard to ozonide formations from olefins.

  DOI：

  10.1002/prac.19953370143
• 作为产物：
  描述：

  1,2-diphenyl-acenaphthylene 在 碳酸氢钠 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以68.6%的产率得到1,2-Diphenylacenaphtenoxid
  参考文献：
  名称：

  �bertragung von drei Sauerstoffen auf die olefinische Doppelbindung von 1,2-Diphenylacenaphthen und 1,2-Diphenyl-3,3,4,4-tetramethylcyclobuten

  摘要：

  The olefinic double bond of 1,2-diphenylacenaphthylene (1) is cleaved into its ozonide 2 (respectively into its Baeyer-Villiger rearrangement product 3) via two independent pathways: Pathway A represents the classical ozonolysis (simultaneous three-oxygen transfer) followed by a Baeyer-Villiger rearrangement, pathway B utilizes a two-step three-oxygen transfer; usual epoxidation (mono-oxygen transfer) is followed by C,C homolysis yielding a deep red diradical which shows fast two-oxygen addition (two-oxygen transfer) of molecular oxygen. The labile intermediate ozonide 2 suffers quantitative Baeyer-Villiger rearrangement under reaction conditions necessary to achieve oxirane C,C-cleavage. Therefore, the particularly stable ozonide 11 from 1,2-diphenyl-3,3,4,4-tetramethylcyclobutene (10) is prepared according to pathway B starting from Arnolds's oxirane 12. Both oxidation methods are compared with regard to ozonide formations from olefins.

  DOI：

  10.1002/prac.19953370143