8-bromo-3-phenyl-1-azaazulene | 660867-81-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 8-bromo-3-phenyl-1-azaazulene
• 英文别名: Cyclohepta[b]pyrrole, 8-bromo-3-phenyl-；8-bromo-3-phenylcyclohepta[b]pyrrole
• CAS: 660867-81-2
• 化学式: C₁₅H₁₀BrN
• 分子量: 284.155
• InChiKey: KYKLNEXYNOEMKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  12.9
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  反式-BETA-苯乙烯硼酸 、 8-bromo-3-phenyl-1-azaazulene 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以66%的产率得到3-phenyl-8-styryl-1-azaazulene
  参考文献：
  名称：

  Syntheses of 2-Formyl-, 2,3-Diformyl- and 8-Formyl-1-azaazulenes

  摘要：

  DOI：

  10.3987/com-07-s(u)6
• 作为产物：
  描述：

  3-phenyl-1-azaazulen-8(1H)-one 在 三溴氧磷 作用下， 反应 1.0h， 以72%的产率得到8-bromo-3-phenyl-1-azaazulene
  参考文献：
  名称：

  Generation and Reactions of 3-Phenyl-7,8-dehydro-1-azaazulene

  摘要：

  3-Phenyl-7,8-dehydro-1-azaazulenes were generated by the treatment of 8-bromo-3-phenyl-1-azaazulenes with potassium t-butoxide in DMSO or in THF in the presence of 16-crown-8-ether, and trapped with diphenylisobenzofuran as 3,7,12-triphenyl-1-aza-7,12-epoxynaphth[2,3-e] azulenes. The structure of the adduct, 2-bromo-3,7,12-triphenyl-1-aza-7,12-epoxynaphth[2,3-e]azulene, was deduced by X-Ray structure analysis. Similar treatment of 8-bromo-3-phenyl-1-azaazulene with potassium t-butoxide in the presence of furan gave 3-phenyl-1-aza-7,12-epoxynaphth[2,3-e]azulene nd 7-phenyl-3H-3a, 3c-dihydro-1-aza-3-oxacyclopenta[3,4]cyclobuta[1,2-ejazulene as cycloadducts.

  DOI：

  10.3987/com-03-s23

文献信息

• Reactions of 3-Phenyl-8-triphenylphosphoimino-1-azaazulene with Aryl Isocyanate, Aryl Isothiocyanate, and Carbon Disulfide
  作者：Noritaka Abe、Kentaro Nagamatsu、Hiroyuki Fujii、Akikazu Kakehi

  DOI：10.3987/com-04-s(p)25

  日期：——

  Reaction of 3-phenyl-8-triphenylphosphoimino-1-azaazulene (1) with some aryl isocyanates gave 2-arylimino-4-phenyl-2,2a-dihydro-1,2a-diazacyclopent[cd]azulenes (2) and 8-arylimino-1,8-dihydro-1-azaazulenes (3). Reaction of 1 with p-toluenesulfonyl isocyanate gave 2-imino-3-(p-methylphenyl)-4-phenyl-2,2a-dihydro-1,2a-diazacyclopent[cd]azulene as cyclization-rearrangement product. Reaction of phenyl

  3-phenyl-8-triphenylphosphoimino-1-azaazulene (1) 与一些芳基异氰酸酯反应得到 2-arylimino-4-phenyl-2,2a-dihydro-1,2a-diazacyclopent[cd]azulenes (2) 和 8- arylimino-1,8-dihydro-1-azaazulenes (3)。1 与对甲苯磺酰基异氰酸酯反应得到 2-亚氨基-3-(对甲基苯基)-4-苯基-2,2a-二氢-1,2a-二氮杂环戊[cd]azulene 作为环化-重排产物。异硫氰酸苯酯反应得到2。在X射线结构分析和分子轨道计算的基础上，讨论了8-亚氨基-1,8-二氢-1-氮杂薁(3)和8-氨基-1-氮杂薁之间的互变异构。
• Syntheses of 2-Formyl-, 2,3-Diformyl- and 8-Formyl-1-azaazulenes
  作者：Noritaka Abe、Kazuya Koizumi、Chikara Miyake、Tomoyuki Ariyoshi、Kenji Umeda、Noriko Yamauchi、Shoji Tagashira、Yoshiko Murakami、Hiroyuki Fujii

  DOI：10.3987/com-07-s(u)6

  日期：——
• Generation and Reactions of 3-Phenyl-7,8-dehydro-1-azaazulene
  作者：Noritaka Abe、Masao Yoshitsugu、Hiroyuki Fujii、Akikazu Kakehi

  DOI：10.3987/com-03-s23

  日期：——

  3-Phenyl-7,8-dehydro-1-azaazulenes were generated by the treatment of 8-bromo-3-phenyl-1-azaazulenes with potassium t-butoxide in DMSO or in THF in the presence of 16-crown-8-ether, and trapped with diphenylisobenzofuran as 3,7,12-triphenyl-1-aza-7,12-epoxynaphth[2,3-e] azulenes. The structure of the adduct, 2-bromo-3,7,12-triphenyl-1-aza-7,12-epoxynaphth[2,3-e]azulene, was deduced by X-Ray structure analysis. Similar treatment of 8-bromo-3-phenyl-1-azaazulene with potassium t-butoxide in the presence of furan gave 3-phenyl-1-aza-7,12-epoxynaphth[2,3-e]azulene nd 7-phenyl-3H-3a, 3c-dihydro-1-aza-3-oxacyclopenta[3,4]cyclobuta[1,2-ejazulene as cycloadducts.