2-Phenyl-1-aza-4,9-methanocyclopentacycloundecene | 128316-63-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Phenyl-1-aza-4,9-methanocyclopentacycloundecene
• 英文别名: 2-phenyl-4,9-methanocycloundecapyrrole
• CAS: 128316-63-2
• 化学式: C₂₀H₁₅N
• 分子量: 269.346
• InChiKey: YPKLYFNPFLPBNJ-ONUDSTLESA-N

物化性质

• 熔点：
  72-77 °C (decomp)
• 沸点：
  537.5±50.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.68
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  12.36
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  (Z)-4-Phenyl-5-aza-tricyclo[8.4.1.0^2,6]pentadeca-1(14),2(6),3,8,10,12-hexaene 在 nickel(IV) oxide 作用下， 以 苯 为溶剂， 反应 0.5h， 以16%的产率得到2-Phenyl-1-aza-4,9-methanocyclopentacycloundecene
  参考文献：
  名称：

  On the reaction of (vinylimino)phosphorane and related compounds. 22. Syntheses and structural studies of methanocycloundeca[b]pyrrole ring systems

  摘要：

  Novel 2-phenyl-6,11- and 2-phenyl-4,9-methanocycloundeca[b]pyrroles (15a and 16a) were synthesized in moderate yields by the reaction of 3,8-methano[11]annulenone (3), a 10pi-electron vinylogue of tropone, with [(l-phenylvinyl)imino]triphenylphosphorane (8a) and subsequent dehydrogenation. Similarly, the reaction of the annulenone 3 with (inden-3-ylimino)tributylphosphorane (8c) and subsequent aromatization afforded 7,12- and 9,14-methano-15H-cycloundeca[b]indeno[2,3-d]pyrroles (15c and 16c), which also have methanocycloundeca[b]pyrrole ring systems. Preparation of 2-phenyl-5,10-methanocycloundeca[b]pyrrole (17), an isomer of both 15a and 16a, was also accomplished in low yield by the reaction of 4,9-methano[ll]annulenone (5) with an excess of [(1-phenylvinyl)imino]tributylphosphorane (8d). The reactivity of annulenone 5 with (vinylimino)phosphoranes was found to be quite low as compared to the higher reactivity of annulenone 3 and tropone. Compounds 15a,c, 16a,c, and 17 are the first nitrogen analogues of cyclopentacycloundecene ring systems which have vinylogous structures of 1-azaazulene. Structures of the products obtained were examined by H-1 NMR spectra and UV spectra. The H-1 NMR spectra clarified that the compounds 15a,c, 16a,c, and 17 are aromatic molecules having a diatropic 14pi-electron system, and 5,10-methano derivative 17 has a more diatropic nature than the compounds 15a,c and 16a,c. The UV spectra of 15a,c, 16a,c, and 17 exhibited increased cyclic conjugation of the aromatic perimeter according to a bathochromic shift of the longest absorption maxima as compared to the corresponding 1-azaazulene derivatives.

  DOI：

  10.1021/jo00046a010

文献信息

• Synthesis and spectroscopic properties of 1-azamkthanocyclopentacycloundecene ring systems
  作者：Makoto Nitta、Nobuhiro Kanomata、Masaru Tada

  DOI：10.1016/s0040-4039(00)88788-2

  日期：1990.1