1,4-Diphenyl-1H,4H-1,4-epoxido-naphtho[1,8-de][1,2]dioxepin | 24516-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,4-Diphenyl-1H,4H-1,4-epoxido-naphtho[1,8-de][1,2]dioxepin
• CAS: 24516-74-3
• 化学式: C₂₄H₁₆O₃
• 分子量: 352.389
• InChiKey: XFTBAVFUQTVTMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.23
• 重原子数：
  27.0
• 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：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1,4-Diphenyl-1H,4H-1,4-epoxido-naphtho[1,8-de][1,2]dioxepin 以 二硫化碳 为溶剂， 反应 168.0h， 以71%的产率得到3,5,8,10-Bis(1',8'-naphthylen)-3,5,8,10-tetraphenyl-1,2,4,6,7,9-hexaoxacyclodecan
  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 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以80%的产率得到1,4-Diphenyl-1H,4H-1,4-epoxido-naphtho[1,8-de][1,2]dioxepin
  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

文献信息

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

  DOI：——

  日期：——