1,2,5,6,9,10,12,13-octamethyldibenzo[fg,op]naphthacene | 1093864-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: 1,2,5,6,9,10,12,13-octamethyldibenzo[fg,op]naphthacene
• 英文别名: 4,5,9,10,15,16,21,22-Octamethylhexacyclo[10.10.2.02,7.08,24.013,18.019,23]tetracosa-1(22),2(7),3,5,8,10,12(24),13(18),14,16,19(23),20-dodecaene；4,5,9,10,15,16,21,22-octamethylhexacyclo[10.10.2.02,7.08,24.013,18.019,23]tetracosa-1(22),2(7),3,5,8,10,12(24),13(18),14,16,19(23),20-dodecaene
• CAS: 1093864-24-4
• 化学式: C₃₂H₃₀
• 分子量: 414.59
• InChiKey: UOCKZWPNYDRCLV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  32
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  3,3''',4,4',4'',4''',5',5''-octamethyl-1,1',2',1'',2'',1'''-quaterphenyl 在 五氯化钼 作用下， 以 二氯甲烷 为溶剂， 以33%的产率得到1,2,5,6,9,10,12,13-octamethyldibenzo[fg,op]naphthacene
  参考文献：
  名称：

  Rearrangements in the Scholl oxidation: implications for molecular architectures

  摘要：

  Rearrangements readily occur in Scholl oxidations and interfere with the construction of certain molecular architectures. 3,3"',4,4',4 '',4"',5',5 ''-Octamethoxy-1,1',2',1 '',2 '',1"'-quaterphenyl and 3,3"',4,4',4 '',4"',5',5'-octamethyl-1,1',2',1 '',2 '',1"'-quaterphenyl, which were conceived as precursors to benzenoid strips, rearranged under Scholl conditions to the unexpected C-2v-substituted products 1,2,5,6,9,10,12,13-octamethoxydibenzo[fg,op]naphthacene and 1,2,5,6,9,10,12,13-octamethyldibenzo[fg,op]naphthacene. This corrects a widely propagated error in the literature in which the assignments of 1,2,5,6,9,10,12,13-octamethoxydibenzo[fg,op]naphthacene (C-2v) and 1,2,5,6,8,9,12,13-octamethoxydibenzo[fg,op]naphthacene (C-2h) are crossed. A mechanism involving the migration of an aryl ring on a it arenium cation intermediate is proposed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.09.105

文献信息

• Rearrangements in the Scholl oxidation: implications for molecular architectures
  作者：Jason L. Ormsby、Tessa D. Black、Cameron L. Hilton、Bharat、Benjamin T. King

  DOI：10.1016/j.tet.2008.09.105

  日期：2008.12

  Rearrangements readily occur in Scholl oxidations and interfere with the construction of certain molecular architectures. 3,3"',4,4',4 '',4"',5',5 ''-Octamethoxy-1,1',2',1 '',2 '',1"'-quaterphenyl and 3,3"',4,4',4 '',4"',5',5'-octamethyl-1,1',2',1 '',2 '',1"'-quaterphenyl, which were conceived as precursors to benzenoid strips, rearranged under Scholl conditions to the unexpected C-2v-substituted products 1,2,5,6,9,10,12,13-octamethoxydibenzo[fg,op]naphthacene and 1,2,5,6,9,10,12,13-octamethyldibenzo[fg,op]naphthacene. This corrects a widely propagated error in the literature in which the assignments of 1,2,5,6,9,10,12,13-octamethoxydibenzo[fg,op]naphthacene (C-2v) and 1,2,5,6,8,9,12,13-octamethoxydibenzo[fg,op]naphthacene (C-2h) are crossed. A mechanism involving the migration of an aryl ring on a it arenium cation intermediate is proposed. (C) 2008 Elsevier Ltd. All rights reserved.