1-(4-chlorophenyl)-2,3,4,5,6-pentaphenylbenzene | 1542081-37-7

• 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: 1-(4-chlorophenyl)-2,3,4,5,6-pentaphenylbenzene
• 英文别名: 1-(4-Chlorophenyl)-2,3,4,5,6-pentakis-phenylbenzene
• CAS: 1542081-37-7
• 化学式: C₄₂H₂₉Cl
• 分子量: 569.145
• InChiKey: YNWDGTMVXAKOKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.34
• 重原子数：
  43.0
• 可旋转键数：
  6.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorophenyl)-2,3,4,5,6-pentaphenylbenzene 在 溴 、 叔丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 [4-[2,4-Bis(4-bromophenyl)-6-(4-chlorophenyl)-3,5-bis(4-trimethylsilylphenyl)phenyl]phenyl]-trimethylsilane
  参考文献：
  名称：

  Selective Alternate Derivatization of the Hexaphenylbenzene Framework through a Thermodynamically Controlled Halogen Dance

  摘要：

  We report a practical synthetic protocol and mechanistic details for the selective alternate derivatization of the hexaphenylbenzene (HPB) framework through a thermodynamically controlled halogen dance. The stability of the alternately trilithiated species of HPB is interpreted by the through-space interaction at the ipso-carbons of the phenyl groups of the HPB framework. By using this approach, C-3-symmetric and lower-symmetric HPB derivatives possessing two or three kinds of substituents on the periphery have become easily and practically available.

  DOI：

  10.1021/ol500041j
• 作为产物：
  描述：

  1-氯-4-(苯基乙炔基)苯 、 四苯基环戊二烯酮 以 二苯醚 为溶剂， 反应 3.0h， 以91%的产率得到1-(4-chlorophenyl)-2,3,4,5,6-pentaphenylbenzene
  参考文献：
  名称：

  Selective Alternate Derivatization of the Hexaphenylbenzene Framework through a Thermodynamically Controlled Halogen Dance

  摘要：

  We report a practical synthetic protocol and mechanistic details for the selective alternate derivatization of the hexaphenylbenzene (HPB) framework through a thermodynamically controlled halogen dance. The stability of the alternately trilithiated species of HPB is interpreted by the through-space interaction at the ipso-carbons of the phenyl groups of the HPB framework. By using this approach, C-3-symmetric and lower-symmetric HPB derivatives possessing two or three kinds of substituents on the periphery have become easily and practically available.

  DOI：

  10.1021/ol500041j

文献信息

• Selective Preparation of C 2v -Symmetric Hexaphenylbenzene Derivatives through Sequential Suzuki Coupling
  作者：Tatsuo Kojima、Shuichi Hiraoka、Kazuho Ogata

  DOI：10.1055/s-0037-1610024

  日期：2018.7

  We have developed effective reaction conditions for the ­Suzuki cross-coupling of chlorinated hexaphenylbenzene derivatives. A chloro group on a hexaphenylbenzene framework exhibits a low reactivity to Suzuki cross-coupling, and only nickel catalysts bearing alkyl-substituted phosphine ligands achieved the coupling. With this as a key step, we succeeded in the selective preparation of a C 2v -symmetric hexaphenylbenzene derivative containing two kinds of aryl group.

  我们已经开发出有效的反应条件，用于氯化六苯基苯衍生物的Suzuki交叉偶联反应。苯环上的氯基对Suzuki交叉偶联反应的反应性较低，只有带有烷基取代膦配体的镍催化剂才能实现偶联。通过这一关键步骤，我们成功地选择性制备了一种含有两种芳基的C2v对称的六苯基苯衍生物。