4a,10-Dihydrobenzazulene | 78926-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 4a,10-Dihydrobenzazulene
• 英文别名: 10H-benzoazulene；4a,10-dihydrobenz(a)azulene；4b,10-Dihydrobenzo[a]azulene
• CAS: 78926-69-9
• 化学式: C₁₄H₁₂
• 分子量: 180.249
• InChiKey: VRNPWXONLZMYIO-UHFFFAOYSA-N

物化性质

• 沸点：
  313.5±27.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  2-(苯基甲基)苯甲醛甲苯磺酰腙 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 正戊烷 为溶剂， 反应 2.0h， 生成 4a,10-Dihydrobenzazulene
  参考文献：
  名称：

  Guth, Michael; Kirmse, Wolfgang, Acta Chemica Scandinavica, 1992, vol. 46, # 7, p. 606 - 613

  摘要：

  DOI：

文献信息

• The addition of benzocyclobutenylidene to benzene
  作者：Margaret A. O'Leary、Geoffrey W. Richardson、Dieter Wege

  DOI：10.1016/s0040-4020(01)97702-6

  日期：1981.1

  trans-10-methyl-9a, 10-dihydrobenz[α]azulene 3, respectively. A mechanism involving initially the addition of the carbene benzocyclobutenylidene, or its 2-Me derivative, to the benzene ring is postulated. A proposed intermediate in the reaction, spiro [benzocyclobutene 1,7' cyclohepta-1',3',5'-triene] 12 has been synthesised, and shown to give rise to 4 under the reaction conditions. The rate of rearrangement

  苯并环丁烯酮甲苯磺酸and和2-甲基苯并环丁酮甲苯磺酸the的钠盐在苯中的热分解分别得到9a，10-二氢苯并[α] azulene 4和反式-10-甲基-9a ，10-二氢苯并[α] azulene 3。推测最初涉及将卡宾苯并环丁烯基或其2- Me衍生物加至苯环的机理。反应中所建议的中间体螺[苯并环丁烯1,7'环庚-1'，3'，5'-三烯] 12已合成，显示在反应条件下可生成4。测量了12→4的重排速率，并确定了活化能：Ea＝ 125.9±0.8KJmol -1，A ＝ 1.38×10 14 sec -1。重排的机理必须涉及12的苯并环丁烯部分的开环以产生邻二甲苯中间体，该中间体被假定具有相当大的双自由基特性。在71.8°时，此开环速度比母体苯并环丁烯分子的开环速度快2.7×10 6倍。还研究了2-（7'-环庚-1'，3'，5'三烯基）苯甲醛甲苯磺酰the的钠盐的分解，结果表明生成4a，10-二氢苯并[α]
• Photochemical Decomposition of Benzocyclobutenone p-Toluenesulfonylhydrazone
  作者：Aryeh A. Frimer、Joseph Weiss、Zilpa Rosental

  DOI：10.1021/jo00088a037

  日期：1994.5

  The photochemical decomposition of benzocyclobutenone p-toluenesulfonylhydrazone led to a wide variety of products including the E- and Z-isomers of l,1'-bi(benzocyclobutenylidene) 6a; cis-trans-benzocyclobutenylidene trimer 7; cyclohepatrienes 8-10; benzocyclobutenone azine in it's anti-anti (11), anti-syn (12), and syn-syn conformations (13); anti- and syn-benzocyclobutenone N-benzocyclobutenyl-N-tosylhydrazone (14 and 15, respectively); (benzocyclobutenyl)hydrazine (16); benzocyclobutenyl p-tolyl sulfone (17); and benzocyclobutenone 1. Their isolation, identification and mechanism of formation are discussed. The data indicate that while the addition of arylcarbenes to alkenes results in the preferential formation of the more-hindered syn products, arylcarbene 5 adds to aryl olefins (styrenes and dimer 6) in a stereospecific anti orientation to give the less-hindered product. In addition, the minimal steric effects observed in these systems presumably results from the 90 degrees angle of the cyclobutyl ring, which pulls the phenyl ring back and thus minimizes its steric contribution.
• OLEARU M. A.; RISNARDSON G. W.; WEGE D., TETRAHEDRON, 1981, 37, NO 4 813-823
  作者：OLEARU M. A.、 RISNARDSON G. W.、 WEGE D.

  DOI：——

  日期：——
• Guth, Michael; Kirmse, Wolfgang, Acta Chemica Scandinavica, 1992, vol. 46, # 7, p. 606 - 613
  作者：Guth, Michael、Kirmse, Wolfgang

  DOI：——

  日期：——