2-phenyl-1-azaazulene | 39183-99-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 2-phenyl-1-azaazulene
• 英文别名: 2-phenyl-cyclohepta[b]pyrrole；2-Phenylcyclohepta[b]pyrrole
• CAS: 39183-99-8
• 化学式: C₁₅H₁₁N
• 分子量: 205.259
• InChiKey: GTZWNUVIFRQWDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 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：

  2-phenyl-1-azaazulene 在 N-溴代丁二酰亚胺(NBS) 、 过氧化苯甲酰 作用下， 以 四氯化碳 为溶剂， 反应 4.0h， 以77%的产率得到3-bromo-2-phenyl-1-azaazulene
  参考文献：
  名称：

  Effective Methods for Introducing Some Aryl and Heteroaryl Substituent onto 1-Azaazulene Nuclei

  摘要：

  Introduction of aryl and heteroaryl groups onto 1-azaazulene ring was achieved by addition-elimination reaction and Suzuki coupling. Reaction of 2-chloro-1-azaazulenes with 2-aryllithium and 2-heteroaryllithium followed by dehydrogenation with o-chloranil gave 8-aryl- and 8-heteroaryl-2-chloro-1-azaazulene in good yields. Suzuki coupling of 3-iodo-1-azaazulenens with phenylboronic acid in the presence of Pd catalyst afforded 3-phenyl-1-azaazulenes in excellent yield. Suzuki coupling of 2-bromo-1-azaazulenes with phenylboronic acid gave 2-phenyl-1-azaazulenes. Suzuki coupling of 2,3-dibromo-1-azaazulene with phenylboronic acid preferentially occurred at C-2. Reaction of 3-iodo-1-azaazulene with bis(pinacolato)diboron produced 3,3'-bis(1-azaazulene) derivative.

  DOI：

  10.3987/com-05-s(k)10
• 作为产物：
  描述：

  N-(diphenylphosphinoyl)troponimine 在 palladium on activated charcoal lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 27.5h， 生成 2-phenyl-1-azaazulene
  参考文献：
  名称：

  Takayasu, Tohru; Ito, Koji; Nitta, Makoto, Heterocycles, 1996, vol. 43, # 12, p. 2667 - 2677

  摘要：

  DOI：

文献信息

• Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone<i>O</i>-Pentafluorobenzoyloximes by Palladium-Catalyzed Cyclization and Oxidation
  作者：Shunsuke Chiba、Mitsuru Kitamura、Osamu Saku、Koichi Narasaka

  DOI：10.1246/bcsj.77.785

  日期：2004.4

  Various 1-azaazulenes are synthesized from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by treatment with a catalytic amount of Pd(dba)2–t-Bu3P (dba = dibenzylideneacetone) and triethy...

  通过用催化量的 Pd(dba)2–t-Bu3P（dba = 二亚苄基丙酮）和三乙醚处理，从环庚三烯基甲基酮 O-五氟苯甲酰肟合成各种 1-氮杂环...
• ON THE REACTION OF<i>N</i>-VINYLIMINOPHOSPHORANES. A NOVEL ROUTE TO 1-AZAAZULENE RING SYSTEM UTILIZING AZA-WITTIG REACTION
  作者：Makoto Nitta、Tomoshige Kobayashi

  DOI：10.1246/cl.1986.463

  日期：1986.4.5

  phenylphosphorane, conveniently prepared from α-azidostyrene and triphenylphosphine, readily undergoes an annelation reaction with tropone derivatives to result in the formation of 1-azaazulene ring system.

  N-(1-苯基) 乙烯基亚氨基三苯基膦，方便地由 α-叠氮苯乙烯和三苯基膦制备，容易与托酮衍生物发生退火反应，形成 1-氮杂芴环系统。
• Palladium-Catalyzed Synthesis of 1-Azaazulenes from Cycloheptatrienylmethyl Ketone<i>O</i>-Pentafluorobenzoyl Oximes
  作者：Mitsuru Kitamura、Shunsuke Chiba、Osamu Saku、Koichi Narasaka

  DOI：10.1246/cl.2002.606

  日期：2002.6

  Substituted 1-azaazulenes are synthesized from cycloheptatrienylmethyl ketone O-pentafluorobenzoyloximes by the intramolecular Heck-type amination catalyzed by Pd(dba)2–(t-Bu)3P.

  取代的1-氮杂蒽烯是通过Pd(dba)2–(t-Bu)3P催化的分子内Heck型氨基化反应，从环七烯基甲基酮O-五氟苯甲酰肟合成的。
• On the Reaction of<i>N</i>-Vinyliminophosphoranes. 9. The Synthesis and Reaction of<i>N</i>-(1,3,5-Cycloheptatrienyl)iminophosphoranes to Provide a Novel Route to 1-Azaazulenes
  作者：Yukio Iino、Eijiro Hara、Makoto Nitta

  DOI：10.1246/bcsj.62.1913

  日期：1989.6

  The first syntheses of N-(2,4,6-cycloheptatrienyl)iminophosphoranes (3a, b) and their thermal conversion to N-(1,3,5-cycloheptatrienyl)iminophosphoranes (5a,b) have been studied. The kinetic study of the 1,5-hydrogen migration of 3a,b to N-(1,3,6-cycloheptatrienyl)iminophosphoranes (4a,b) has also been investigated. The reaction of 5b with α-bromoacetophenone derivatives has provided a novel route to the 1-azaazulene ring system, albeit in low yields.

  研究了 N-(2,4,6-环庚三烯基)亚氨基正膦 (3a, b) 的首次合成及其热转化为 N-(1,3,5-环庚三烯基)亚氨基正膦 (5a,b)。还研究了 3a,b 到 N-(1,3,6-环庚三烯基)亚氨基正膦 (4a,b) 的 1,5-氢迁移的动力学研究。 5b与α-溴苯乙酮衍生物的反应为1-氮杂薁环体系提供了一条新的路线，尽管产率较低。
• Nitta, Makoto; Iino, Yukio; Hara, Eijiro, Journal of the Chemical Society. Perkin transactions I, 1989, p. 51 - 56
  作者：Nitta, Makoto、Iino, Yukio、Hara, Eijiro、Kobayashi, Tomoshige

  DOI：——

  日期：——