3-(p-methoxyphenyl)-1-(1H-indenylidene)-5H-dibenzo[a.d]cycloheptene | 1262843-21-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 二苯并环庚烯
• 英文名称: 3-(p-methoxyphenyl)-1-(1H-indenylidene)-5H-dibenzo[a.d]cycloheptene
• 英文别名: 2-[3-(4-Methoxyphenyl)inden-1-ylidene]tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaene
• CAS: 1262843-21-9
• 化学式: C₃₁H₂₂O
• 分子量: 410.515
• InChiKey: AOXSNAOMODIMGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.03
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-(p-methoxyphenyl)-1-(1H-indenylidene)-5H-dibenzo[a.d]cycloheptene 在 五氟化锑 作用下， 以 氯氟磺酰 为溶剂， 生成 Methyl-[4-[3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,9,11,13-heptaenylidene)inden-1-yl]cyclohexa-2,5-dien-1-ylidene]oxidanium
  参考文献：
  名称：

  Dications of 3-Phenyl-indenylidene Dibenzo[a.d]cycloheptene: The Role of Charge in the Antiaromaticity of Cationic Systems

  摘要：

  Dications of 9-(3-phenyl-1H-inden-1-ylidene)-5H-dibenzo[a,d]cycloheptene, 5(2+), were prepared by oxidation with SbF5 in SO2CIF, and their magnetic behavior was compared to dications of 9-(3-phenyl-1H-inden-1-ylidene)-9H-fluorene, 2(2+). The good correlation between the experimental H-1 NMR shifts for the dications that were oxidized cleanly and the chemical shifts calculated by the GAIO method supported the use of the nucleus independent chemical shifts, NICS, to evaluate the antiaromaticity of the indenyl systems of 2(2+)/5(2+) and their unsubstituted parent compounds, 6(2+) and 7(2+), as well as the antiaromaticity of the fluorenyl system of 2(2+)/7(2+) and the aromaticity of the dibenzotropylium system of 5(2+)/6(2+). Antiaromaticity was shown to be directly related to the amount of charge in the antiaromatic systems, with the antiaromatic systems more responsive to changes in the calculated NBO charge than the aromatic systems. The antiaromaticity was also shown to be directly related to the amount of delocalization in the ring system. The aromaticity of the dibenzotropylium system was much less responsive to changes in the amount of charge in the tropylium system, because the aromatic system was much more completely delocalized. Thus, antiaromatic species are more sensitive probes of delocalization than aromatic ones.

  DOI：

  10.1021/jo102220y
• 作为产物：
  描述：

  4-甲氧基苯基溴化镁 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 3-(p-methoxyphenyl)-1-(1H-indenylidene)-5H-dibenzo[a.d]cycloheptene
  参考文献：
  名称：

  Dications of 3-Phenyl-indenylidene Dibenzo[a.d]cycloheptene: The Role of Charge in the Antiaromaticity of Cationic Systems

  摘要：

  Dications of 9-(3-phenyl-1H-inden-1-ylidene)-5H-dibenzo[a,d]cycloheptene, 5(2+), were prepared by oxidation with SbF5 in SO2CIF, and their magnetic behavior was compared to dications of 9-(3-phenyl-1H-inden-1-ylidene)-9H-fluorene, 2(2+). The good correlation between the experimental H-1 NMR shifts for the dications that were oxidized cleanly and the chemical shifts calculated by the GAIO method supported the use of the nucleus independent chemical shifts, NICS, to evaluate the antiaromaticity of the indenyl systems of 2(2+)/5(2+) and their unsubstituted parent compounds, 6(2+) and 7(2+), as well as the antiaromaticity of the fluorenyl system of 2(2+)/7(2+) and the aromaticity of the dibenzotropylium system of 5(2+)/6(2+). Antiaromaticity was shown to be directly related to the amount of charge in the antiaromatic systems, with the antiaromatic systems more responsive to changes in the calculated NBO charge than the aromatic systems. The antiaromaticity was also shown to be directly related to the amount of delocalization in the ring system. The aromaticity of the dibenzotropylium system was much less responsive to changes in the amount of charge in the tropylium system, because the aromatic system was much more completely delocalized. Thus, antiaromatic species are more sensitive probes of delocalization than aromatic ones.

  DOI：

  10.1021/jo102220y

文献信息

• Dications of 3-Phenyl-indenylidene Dibenzo[<i>a</i>.<i>d</i>]cycloheptene: The Role of Charge in the Antiaromaticity of Cationic Systems
  作者：Nancy S. Mills、Francine E. Cheng、Joseph M. Baylan、Cornelia Tirla、Jennifer L. Hartmann、Kiran C. Patel、Bart J. Dahl、Sean P. McClintock

  DOI：10.1021/jo102220y

  日期：2011.1.21

  Dications of 9-(3-phenyl-1H-inden-1-ylidene)-5H-dibenzo[a,d]cycloheptene, 5(2+), were prepared by oxidation with SbF5 in SO2CIF, and their magnetic behavior was compared to dications of 9-(3-phenyl-1H-inden-1-ylidene)-9H-fluorene, 2(2+). The good correlation between the experimental H-1 NMR shifts for the dications that were oxidized cleanly and the chemical shifts calculated by the GAIO method supported the use of the nucleus independent chemical shifts, NICS, to evaluate the antiaromaticity of the indenyl systems of 2(2+)/5(2+) and their unsubstituted parent compounds, 6(2+) and 7(2+), as well as the antiaromaticity of the fluorenyl system of 2(2+)/7(2+) and the aromaticity of the dibenzotropylium system of 5(2+)/6(2+). Antiaromaticity was shown to be directly related to the amount of charge in the antiaromatic systems, with the antiaromatic systems more responsive to changes in the calculated NBO charge than the aromatic systems. The antiaromaticity was also shown to be directly related to the amount of delocalization in the ring system. The aromaticity of the dibenzotropylium system was much less responsive to changes in the amount of charge in the tropylium system, because the aromatic system was much more completely delocalized. Thus, antiaromatic species are more sensitive probes of delocalization than aromatic ones.