endo-2,3-diaza-10,10-dimethoxy-1,4-di(4'-chlorophenyl)tricyclo[5.2.1.5,9]dec-2-ene | 440085-25-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 英文名称: endo-2,3-diaza-10,10-dimethoxy-1,4-di(4'-chlorophenyl)tricyclo[5.2.1.5,9]dec-2-ene
• 英文别名: (1S,2R,6S,7R)-1,7-bis(4-chlorophenyl)-10,10-dimethoxy-8,9-diazatricyclo[5.2.1.02,6]dec-8-ene
• CAS: 440085-25-6
• 化学式: C₂₂H₂₂Cl₂N₂O₂
• 分子量: 417.335
• InChiKey: KVBCDVYULMDJTR-FXELSEDVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  43.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  endo-2,3-diaza-10,10-dimethoxy-1,4-di(4'-chlorophenyl)tricyclo[5.2.1.5,9]dec-2-ene 以 苯 为溶剂， 以100%的产率得到2,4-di(4'-chlorophenyl)-3,3-dimethoxytricyclo[3.3.0.^1,50^2,4]octane
  参考文献：
  名称：

  On the Electronic Character of Localized Singlet 2,2-Dimethoxycyclopentane-1,3-diyl Diradicals:  Substituent Effects on the Lifetime

  摘要：

  Photodenitrogenation of the diazenes 4 affords exclusively the housanes 5 through intramolecular cyclization of the spectrally detected and characterized singlet diradicals 3. The lifetime of singlet diradical 3, determined by transient absorption measurements, depends on the Y and Z substituents at the para position of the phenyl ring and has the following order: Y, Z = OMe, OMe > OMe, CN > CN, CN > OMe, H > Cl, Cl approximately CN, H approximately Me, Me > H, H. This unprecedented substituent effect reveals stabilization of the singlet 2,2-dimethoxycyclopentane-1,3-diyl diradicals 3 through radical, zwitterionic, pi-bonding, and hyperconjugative structures.

  DOI：

  10.1021/ja026301l
• 作为产物：
  描述：

  1,3-双(4-氯苯基)-1,3-丙二酮 在 三氟乙酸 palladium on activated charcoal 、 二苯基二硒醚 、 氢气 、 peroxodisulfate ion 、 肼 作用下， 反应 2.0h， 生成 endo-2,3-diaza-10,10-dimethoxy-1,4-di(4'-chlorophenyl)tricyclo[5.2.1.5,9]dec-2-ene
  参考文献：
  名称：

  On the Electronic Character of Localized Singlet 2,2-Dimethoxycyclopentane-1,3-diyl Diradicals:  Substituent Effects on the Lifetime

  摘要：

  Photodenitrogenation of the diazenes 4 affords exclusively the housanes 5 through intramolecular cyclization of the spectrally detected and characterized singlet diradicals 3. The lifetime of singlet diradical 3, determined by transient absorption measurements, depends on the Y and Z substituents at the para position of the phenyl ring and has the following order: Y, Z = OMe, OMe > OMe, CN > CN, CN > OMe, H > Cl, Cl approximately CN, H approximately Me, Me > H, H. This unprecedented substituent effect reveals stabilization of the singlet 2,2-dimethoxycyclopentane-1,3-diyl diradicals 3 through radical, zwitterionic, pi-bonding, and hyperconjugative structures.

  DOI：

  10.1021/ja026301l