4-(4-Chloro-phenyl)-6-phenyl-3-aza-tricyclo[8.4.1.02,7]pentadeca-1(14),2(7),3,8,10,12-hexaene | 137594-15-1

• 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: 4-(4-Chloro-phenyl)-6-phenyl-3-aza-tricyclo[8.4.1.02,7]pentadeca-1(14),2(7),3,8,10,12-hexaene
• CAS: 137594-15-1
• 化学式: C₂₆H₂₀ClN
• 分子量: 381.904
• InChiKey: GNAYFWCCHMLVFY-UHFFFAOYSA-N

物化性质

• 沸点：
  610.0±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.95
• 重原子数：
  28.0
• 可旋转键数：
  2.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  4-(4-Chloro-phenyl)-6-phenyl-3-aza-tricyclo[8.4.1.02,7]pentadeca-1(14),2(7),3,8,10,12-hexaene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 生成 7,12-亚甲基环癸五烯并[b]吡啶,2-(4-氯苯基)-4-苯基-
  参考文献：
  名称：

  On the reaction of (vinylimino)phosphoranes and related compounds. 20. Syntheses and properties of methanocyclodeca[b]pyridine ring systems

  摘要：

  Novel 2-[(triphenyl- and 2-[(tributylphosphoranylidene)amino]-1,6-methanol[10]annulenes (8x,y) and 3-[(triphenyl- and 3-[(tributylphosphoranylidene)amino]-1,6-methano[10]annulenes (9x,y) were generated by the Staudinger reaction of 2- and 3-azido-1,6-methano[10]annulenes (5 and 6). The compound 8x was inert to alpha,beta-unsaturated ketones, while compounds 8y and 9y were found to react with alpha,beta-unsaturated ketones in enamine-alkylation process followed by aza-Wittig reaction and dehydrogenation to give 7,12- and 5,10-methanocyclodeca[b]pyridines 20a-f and 26a,f, respectively. The reactivity of 8 and 9 as well as the site selectivity of 9 was suggested by their C-13 NMR spectra, in which the carbon signals of the nucleophilic center appear at higher field as compared to those of 1,6-methano[10]annulene. Structural properties of 20a-f and 26a,f were examined by H-1 NMR and UV spectra. The H-1 NMR spectra analyzing aromatic characters clarified both remarkable reduction of a ring current and appearance of bond alternation as compared to the parent 1,6-methano[10]annulene (1). The UV spectra exhibiting a prolonged cyclic conjugation are in contrast to their 10-pi electron analogues, 1,6-methano[10]annulene (1) and quinoline derivatives.

  DOI：

  10.1021/jo00028a040
• 作为产物：
  描述：

  双环[4.4.1]十一碳-1(10),2,4,6,8-五烯 在 溴叠氮化物 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 18.0h， 生成 4-(4-Chloro-phenyl)-6-phenyl-3-aza-tricyclo[8.4.1.02,7]pentadeca-1(14),2(7),3,8,10,12-hexaene
  参考文献：
  名称：

  On the reaction of (vinylimino)phosphoranes and related compounds. 20. Syntheses and properties of methanocyclodeca[b]pyridine ring systems

  摘要：

  Novel 2-[(triphenyl- and 2-[(tributylphosphoranylidene)amino]-1,6-methanol[10]annulenes (8x,y) and 3-[(triphenyl- and 3-[(tributylphosphoranylidene)amino]-1,6-methano[10]annulenes (9x,y) were generated by the Staudinger reaction of 2- and 3-azido-1,6-methano[10]annulenes (5 and 6). The compound 8x was inert to alpha,beta-unsaturated ketones, while compounds 8y and 9y were found to react with alpha,beta-unsaturated ketones in enamine-alkylation process followed by aza-Wittig reaction and dehydrogenation to give 7,12- and 5,10-methanocyclodeca[b]pyridines 20a-f and 26a,f, respectively. The reactivity of 8 and 9 as well as the site selectivity of 9 was suggested by their C-13 NMR spectra, in which the carbon signals of the nucleophilic center appear at higher field as compared to those of 1,6-methano[10]annulene. Structural properties of 20a-f and 26a,f were examined by H-1 NMR and UV spectra. The H-1 NMR spectra analyzing aromatic characters clarified both remarkable reduction of a ring current and appearance of bond alternation as compared to the parent 1,6-methano[10]annulene (1). The UV spectra exhibiting a prolonged cyclic conjugation are in contrast to their 10-pi electron analogues, 1,6-methano[10]annulene (1) and quinoline derivatives.

  DOI：

  10.1021/jo00028a040