trans-14b,14c-dimethyl-14b,14c-dihydronaphtho<2,1,8-qra>naphthacene | 80697-10-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: trans-14b,14c-dimethyl-14b,14c-dihydronaphtho<2,1,8-qra>naphthacene
• 英文别名: (23R,24R)-23,24-dimethylhexacyclo[14.6.2.02,11.04,9.013,23.020,24]tetracosa-1(22),2,4,6,8,10,12,14,16,18,20-undecaene
• CAS: 80697-10-5
• 化学式: C₂₆H₂₀
• 分子量: 332.445
• InChiKey: CPWKKHQNBRAYCA-CLJLJLNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  26
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  在 diiron nonacarbonyl 作用下， 以 苯 为溶剂， 反应 0.08h， 以37%的产率得到trans-14b,14c-dimethyl-14b,14c-dihydronaphtho<2,1,8-qra>naphthacene
  参考文献：
  名称：

  An Experimental Estimation of Aromaticity Relative to That of Benzene. The Synthesis and NMR Properties of a Series of Highly Annelated Dimethyldihydropyrenes: Bridged Benzannulenes

  摘要：

  The synthesis of 13 trans-dimethyldihydropyrenes (bridged [14]annulenes) fused to one or more benzene, naphthalene, phenanthrene, phenalene, or quinoxaline rings and 6 cis-dihydropyrene derivatives from benzenoid precursors using either a thiacyclophane route or an electrocyclic addition of a furan to an annulyne followed by deoxygenation is reported. Their H-1 NMR spectra are studied in detail to obtain correlations between (3)J(H,H) coupling constants and the internal methyl proton chemical shifts and also between the latter and the more distant external annulene ring proton shifts. These linear correlations are then used to obtain a relationship between the relative aromaticity of benzene and the fused ring in question, such that the aromaticity of the fused ring can be estimated relative to that of a benzene ring simply from a measurement of chemical shift in the fused annulene.

  DOI：

  10.1021/ja00110a008

文献信息

• The synthesis and trapping of the first [14]annulyne with benzyne like reactivity. A fast route to several annelated bridged annulenes.
  作者：Reginald H. Mitchell、Pengzu Zhou

  DOI：10.1016/s0040-4039(00)98049-3

  日期：1990.1
• An Experimental Estimation of Aromaticity Relative to That of Benzene. The Synthesis and NMR Properties of a Series of Highly Annelated Dimethyldihydropyrenes: Bridged Benzannulenes
  作者：Reginald H. Mitchell、Vivekanantan S. Iyer、Nasr Khalifa、Ramanathan Mahadevan、Santhanagopalan Venugopalan、Sirimevan Ananda Weerawarna、Pengzu Zhou

  DOI：10.1021/ja00110a008

  日期：1995.2

  The synthesis of 13 trans-dimethyldihydropyrenes (bridged [14]annulenes) fused to one or more benzene, naphthalene, phenanthrene, phenalene, or quinoxaline rings and 6 cis-dihydropyrene derivatives from benzenoid precursors using either a thiacyclophane route or an electrocyclic addition of a furan to an annulyne followed by deoxygenation is reported. Their H-1 NMR spectra are studied in detail to obtain correlations between (3)J(H,H) coupling constants and the internal methyl proton chemical shifts and also between the latter and the more distant external annulene ring proton shifts. These linear correlations are then used to obtain a relationship between the relative aromaticity of benzene and the fused ring in question, such that the aromaticity of the fused ring can be estimated relative to that of a benzene ring simply from a measurement of chemical shift in the fused annulene.