8-amino-3-phenyl-1-azaazulene | 63725-08-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 8-amino-3-phenyl-1-azaazulene
• 英文别名: 3-phenylcyclohepta[b]pyrrol-8-amine
• CAS: 63725-08-6
• 化学式: C₁₅H₁₂N₂
• 分子量: 220.274
• InChiKey: CSPVBTPHMMCTEX-UHFFFAOYSA-N

物化性质

• 熔点：
  200-201 °C(Solv: benzene (71-43-2))
• 沸点：
  478.5±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  38.91
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  8-amino-3-phenyl-1-azaazulene 在 palladium diacetate 三乙胺 作用下， 以 xylene 、 苯 为溶剂， 反应 224.0h， 生成 3-(4-methylphenyl)-6-phenyl-2,4-diazatricyclo[5.4.1.04,12]dodeca-1(12),2,6,8,10-pentaene
  参考文献：
  名称：

  Some Reactions of 3-Phenyl-8-triphenyl-phosphoimino-1-azaazulene

  摘要：

  Reaction of 3-phenyl-8-triphenylphosphoimino-1-azaazulene (1) with arylaldehyde gave 2-aryl-4-phenyl-3H-1,2a-diazacyclopent[cd]azulenes. Reaction of I with trans-cinnamaldehyde gave 3-benzyl-1-pheny-2a,5-diazabenz[cd]azulene as cyclization product. Cycloaddition reaction of 1 with dimethyl acetylenedicarboxylate gave tetramethyl 4-phenyl-9,9b-diazaindeno[4,3a,3,2-bcd]azulene-1,2,3,9a-tetracarboxylate and hexamethyl 6phenyl-3aH-10c-azaacephenanthryene-1,2,3,3a,4,5-hexacarboxylate.

  DOI：

  10.3987/com-03-9982
• 作为产物：
  描述：

  8-chloro-3-phenyl-1-azaazulene 以65%的产率得到
  参考文献：
  名称：

  YAMANE K.; FUJIMORI K.; SIN J.-K.; NOZOE T., BULL. CHEM. SOC. JAP. , 1977, 50, NO 5, 1184-1190

  摘要：

  DOI：

文献信息

• Synthesis and Heteroannulation of 3,4-Dibenzoyl-1-phenyl-2a,5-diazabenz[<i>cd</i>]azulene
  作者：Noritaka Abe、Tamae Ueno

  DOI：10.1246/bcsj.63.2121

  日期：1990.7

  4-Dibenzoyl-1-phenyl-2a,5-diazabenz[cd]azulene (2b) was synthesized by cycloaddition of 8-amino3-phenyl-1-azaazulene with dibenzoylacetylene. Heteroannulation to 2b has been achieved by reactions with hydrazine and phosphorus pentasulfide.

  3,4-Dibenzoyl-1-phenyl-2a,5-diazabenz[cd]azulene (2b) 是通过 8-amino3-phenyl-1-azaazulene 与二苯甲酰乙炔的环加成反应合成的。已通过与肼和五硫化二磷反应实现对 2b 的杂环化。
• Cycloaddition Reactions of 2-Acetylamino-, 2-Alkylamino-, 8-Ethylamino-, and 8-Acetylamino-1-azaazulenes with Dimethyl Acetylenedicarboxylate
  作者：Noritaka Abe、Yoshimasa Fukazawa、Yoshimasa Hirai、Tosio Sakurai、Kunio Urushido、Akikazu Kakehi

  DOI：10.1246/bcsj.65.1784

  日期：1992.7

  amino)-1-azaazulenes with dimethyl acetylenedicarboxylate (DMAD) were investigated. Treatment of ethyl 2-acetylamino-1-azaazulene-3-carboxylate with DMAD in refluxing acetonitrile gave 9-ethyl 1,2,3-trimethyl 3a-azacyclopent[a]azulene-1,2,3,9-tetracarboxylate, 5-ethyl 1,2,2a,3-tetramethyl 4-acetyl-2a,3-dihydro-4H-4, 10b-diazapentaleno[1,6-aj]azulene-1,2,2a,3,5-pentacarboxylate (3a), and dimethyl (10-ethoxycar

  研究了 2-和 8-（取代氨基）-1-氮杂氮杂与乙炔二羧酸二甲酯 (DMAD) 的反应。在回流乙腈中用 DMAD 处理 2-乙酰氨基-1-氮杂环戊烯-3-羧酸乙酯，得到 1,2,3-三甲基 3a-氮杂环戊 [a] 氮杂环戊烷-1,2,3,9-四羧酸 9-乙酯，5- 1,2,2a,3-四甲基 4-乙酰基-2a,3-dihydro-4H-4, 10b-diazapentaleno[1,6-aj]azulene-1,2,2a,3,5-pentacarboxylate (3a)和（10-乙氧基羰基-4-甲氧基羰基-2,4a-二氢-2-氧代-2H-1,4a-二氮杂苯并[a]azlen-3-基）马来酸二甲酯。化合物3a热重排为9-乙基2,3,10,11-四甲基1-乙酰-2,3,4,4a-四氢-1H-1,4-二氮杂-3,4a-乙烯芴-2,3,9 ,10,11-五羧酸盐。2-烷基氨基-1-氮杂氮杂-3-羧
• Synthesis and Some Reactions of 1,8-Diamino-1-azaazulenium Salts
  作者：Noritaka Abe、Kunihiko Odagiri、Hiroyuki Fujii、Akikazu Kakehi

  DOI：10.3987/com-99-8769

  日期：——

  Amination of 8-amino-3-phenyl-1-azaazulene gave 1,8-diamino-3-phenyl-1-azaazulenium salt (2). Reactions of the salt (2) with triethyl orthoformate and acetic anhydride gave 1-phenyl-2a,3, 5-triazabenz[cd]azulene derivatives (3a and 3b). The compound (3a) was also obtained by the reaction of 2 with diethyl ethoxymethylenemalonate in the presence of potassium carbonate. The reaction of 2 with ethyl pyruvate gave 4-acetyl-1-phenyl-2a, 3,5-triazabenz[cd]azulene (3c). The structure of 3c was deduced by X-Ray structure analysis. Reaction of 2 with acetylenic esters in the presence of potassium carbonate gave 2a,3-diazabenz[cd]azulene derivatives (10a, b).
• Synthesis and Some Properties of Phosphoimino-1-azaazulene Derivatives
  作者：Noritaka Abe、Hiroyuki Fujii、Kenji Tahara、Motoo Shiro

  DOI：10.3987/com-01-9288

  日期：——

  3-Phenyl-8-triphenylphosphoimino- and 2-triphenylphosphoimino-1-azaazulenes were prepared by the reaction of the corresponding 8- and 2-amino-1-azaazulenes with triphenylphosphine dibromide. The structure of 3-phenyl-8-triphenylphosphoimino-1-azaazulene was investigated by X-Ray crystallographic analysis and molecular orbital calculation. The P-atom has trigonal bipiramidal coordination and the intramolecular distance between the N-1 and the P-atom is 2.762(6) Angstrom, the existence of an interaction between N-1 and the P-atom is considered.
• Synthesis and Cycloaddition Reaction of 2a,5-Diazacyclohept[cd]indebes: Formation of Cyclohept[ef]-6-azacycl[3.2.2.]azine System
  作者：Noritaka Abe

  DOI：10.3987/r-1987-01-0059

  日期：——