7-(p-Bromophenyl)-1,2:3,4:5,6-tris(bicyclo<2.2.2>octeno)cycloheptatriene

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 7-(p-Bromophenyl)-1,2:3,4:5,6-tris(bicyclo<2.2.2>octeno)cycloheptatriene
• 英文别名: 7-(p-Bromophenyl)-1,2:3,4:5,6-tris(bicyclo[2.2.2]octeno)cycloheptatriene；15-(4-Bromophenyl)heptacyclo[15.2.2.24,7.210,13.02,16.03,8.09,14]pentacosa-2(16),3(8),9(14)-triene
• 化学式: C₃₁H₃₅Br
• 分子量: 487.523
• InChiKey: OXUWMHVIQMETAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  32
• 可旋转键数：
  1
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  7-(p-Bromophenyl)-1,2:3,4:5,6-tris(bicyclo<2.2.2>octeno)cycloheptatriene 、 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.25h， 以64.3%的产率得到p-Bis<2,3:4,5:6,7-tris(bicyclo<2.2.2>octeno)cycloheptatrien-1-yl>benzene
  参考文献：
  名称：

  Syntheses, Properties, and Redox Behaviors of 7-Phenyl-1,2:3,4:5,6-tris(bicyclo[2.2.2]octeno)tropylium Ion and the Dications Composed of Two 1,2:3,4:5,6-Tris(bicyclo[2.2.2]octeno)tropylium Units Connected by para- and meta-Phenylene Spacers

  摘要：

  The stable carbodications composed of two tris(bicyclo[2.2.2]octeno)tropylium units connected by a p-phenylene (7) and a m-phenylene spacer (8) were synthesized, together with the corresponding monocation having a 7-phenyl substituent (6) as a reference compound, and their properties were fully characterized. The pK(R+) values of 6, 7, and 8 were determined in 50% aqueous acetonitrile to be 12.0, 11.5, and 10.4, respectively. The 7-phenyl substituent, which is supposedly nearly perpendicular to the tropylium ring, destabilizes the cation by 1 pK unit. The two cation units at the p-phenylene positions in 7 were neutralized simultaneously, but those in 8 were neutralized stepwise; the pK(R+) value for the half-neutralized monocation was 12.2. Upon one-electron reduction monocation 6 gave a stable free radical persisting in solution at room temperature. p-Phenylene-connected dication 7 did not give any radical species but instead gave a closed-shell hydrocarbon upon one-step, two-electron reduction. In the case of m-phenylene-connected dication 8, two very closely spaced reduction steps were observed upon cyclic voltammetry, and the resulting fully reduced species was identified as a triplet diradical by low-temperature ESR.

  DOI：

  10.1021/jo00103a023
• 作为产物：
  描述：

  1,4-二溴苯 、 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.12h， 以89.5%的产率得到7-(p-Bromophenyl)-1,2:3,4:5,6-tris(bicyclo<2.2.2>octeno)cycloheptatriene
  参考文献：
  名称：

  Syntheses, Properties, and Redox Behaviors of 7-Phenyl-1,2:3,4:5,6-tris(bicyclo[2.2.2]octeno)tropylium Ion and the Dications Composed of Two 1,2:3,4:5,6-Tris(bicyclo[2.2.2]octeno)tropylium Units Connected by para- and meta-Phenylene Spacers

  摘要：

  The stable carbodications composed of two tris(bicyclo[2.2.2]octeno)tropylium units connected by a p-phenylene (7) and a m-phenylene spacer (8) were synthesized, together with the corresponding monocation having a 7-phenyl substituent (6) as a reference compound, and their properties were fully characterized. The pK(R+) values of 6, 7, and 8 were determined in 50% aqueous acetonitrile to be 12.0, 11.5, and 10.4, respectively. The 7-phenyl substituent, which is supposedly nearly perpendicular to the tropylium ring, destabilizes the cation by 1 pK unit. The two cation units at the p-phenylene positions in 7 were neutralized simultaneously, but those in 8 were neutralized stepwise; the pK(R+) value for the half-neutralized monocation was 12.2. Upon one-electron reduction monocation 6 gave a stable free radical persisting in solution at room temperature. p-Phenylene-connected dication 7 did not give any radical species but instead gave a closed-shell hydrocarbon upon one-step, two-electron reduction. In the case of m-phenylene-connected dication 8, two very closely spaced reduction steps were observed upon cyclic voltammetry, and the resulting fully reduced species was identified as a triplet diradical by low-temperature ESR.

  DOI：

  10.1021/jo00103a023

文献信息

• Syntheses, Properties, and Redox Behaviors of 7-Phenyl-1,2:3,4:5,6-tris(bicyclo[2.2.2]octeno)tropylium Ion and the Dications Composed of Two 1,2:3,4:5,6-Tris(bicyclo[2.2.2]octeno)tropylium Units Connected by para- and meta-Phenylene Spacers
  作者：Koichi Komatsu、Tohru Nishinaga、Naoko Maekawa、Akifumi Kagayama、Ken'ichi Takeuchi

  DOI：10.1021/jo00103a023

  日期：1994.12

  The stable carbodications composed of two tris(bicyclo[2.2.2]octeno)tropylium units connected by a p-phenylene (7) and a m-phenylene spacer (8) were synthesized, together with the corresponding monocation having a 7-phenyl substituent (6) as a reference compound, and their properties were fully characterized. The pK(R+) values of 6, 7, and 8 were determined in 50% aqueous acetonitrile to be 12.0, 11.5, and 10.4, respectively. The 7-phenyl substituent, which is supposedly nearly perpendicular to the tropylium ring, destabilizes the cation by 1 pK unit. The two cation units at the p-phenylene positions in 7 were neutralized simultaneously, but those in 8 were neutralized stepwise; the pK(R+) value for the half-neutralized monocation was 12.2. Upon one-electron reduction monocation 6 gave a stable free radical persisting in solution at room temperature. p-Phenylene-connected dication 7 did not give any radical species but instead gave a closed-shell hydrocarbon upon one-step, two-electron reduction. In the case of m-phenylene-connected dication 8, two very closely spaced reduction steps were observed upon cyclic voltammetry, and the resulting fully reduced species was identified as a triplet diradical by low-temperature ESR.