NO2/Me-FDPN | 200001-80-5

• 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: NO2/Me-FDPN
• 英文别名: 7-(2-Fluoro-4-methylphenyl)-7-(4-nitrophenyl)bicyclo[2.2.1]heptane；7-(2-fluoro-4-methylphenyl)-7-(4-nitrophenyl)bicyclo[2.2.1]heptane
• CAS: 200001-80-5
• 化学式: C₂₀H₂₀FNO₂
• 分子量: 325.383
• InChiKey: IAFYAAJBGPCHBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  NO2/Me-FDPN 在 palladium on activated charcoal 氢气 作用下， 以 乙醚 为溶剂， 反应 2.0h， 以100%的产率得到7-(2-fluoro-4-methylphenyl)-7-(4-aminophenyl)norbornane
  参考文献：
  名称：

  Hindered Rotation in Diphenylmethane Derivatives. Electrostatic vs Charge-Transfer and Homoconjugative Aryl−Aryl Interactions

  摘要：

  A series of p,p'-disubstituted 7-phenyl-7-(2-fluorophenyl)norbornanes 5xy has been prepared, and the barrier (Delta G(#)) to 160 degrees libration around the 2-fluoroaryl-norbornane bond has been measured by DNMR. There is spectroscopic evidence of strong homoconjugative and charge-transfer (CT) interactions between both aryl groups of 5xy. However, the relationship between Delta G(#) and the nature of the substituents X and Y is accounted for only by electrostatic interactions between both aryl groups in the ground state as well as in the transition state of the libration. Therefore, the notion of CT and aromatic homoconjugation as strong attractive forces between aryl groups should be definitively rejected.

  DOI：

  10.1021/ja971388+
• 作为产物：
  描述：

  7-phenyl-7-norbornanol 在 三氯化铝 、 氯化亚砜 、 nitronium tetrafluoborate 、 18-冠醚-6 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 NO2/Me-FDPN
  参考文献：
  名称：

  Hindered Rotation in Diphenylmethane Derivatives. Electrostatic vs Charge-Transfer and Homoconjugative Aryl−Aryl Interactions

  摘要：

  A series of p,p'-disubstituted 7-phenyl-7-(2-fluorophenyl)norbornanes 5xy has been prepared, and the barrier (Delta G(#)) to 160 degrees libration around the 2-fluoroaryl-norbornane bond has been measured by DNMR. There is spectroscopic evidence of strong homoconjugative and charge-transfer (CT) interactions between both aryl groups of 5xy. However, the relationship between Delta G(#) and the nature of the substituents X and Y is accounted for only by electrostatic interactions between both aryl groups in the ground state as well as in the transition state of the libration. Therefore, the notion of CT and aromatic homoconjugation as strong attractive forces between aryl groups should be definitively rejected.

  DOI：

  10.1021/ja971388+

文献信息

• Hindered Rotation in Diphenylmethane Derivatives. Electrostatic vs Charge-Transfer and Homoconjugative Aryl−Aryl Interactions
  作者：A. García Martínez、J. Osío Barcina、A. de Fresno Cerezo、R. Gutiérrez Rivas

  DOI：10.1021/ja971388+

  日期：1998.2.1

  A series of p,p'-disubstituted 7-phenyl-7-(2-fluorophenyl)norbornanes 5xy has been prepared, and the barrier (Delta G(#)) to 160 degrees libration around the 2-fluoroaryl-norbornane bond has been measured by DNMR. There is spectroscopic evidence of strong homoconjugative and charge-transfer (CT) interactions between both aryl groups of 5xy. However, the relationship between Delta G(#) and the nature of the substituents X and Y is accounted for only by electrostatic interactions between both aryl groups in the ground state as well as in the transition state of the libration. Therefore, the notion of CT and aromatic homoconjugation as strong attractive forces between aryl groups should be definitively rejected.