2-exo-7-anti-Hydroxybenzonorborn-5-ene | 93955-70-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2-exo-7-anti-Hydroxybenzonorborn-5-ene
• 英文别名: (1R,8R,9S)-tricyclo[6.2.1.02,7]undeca-2,4,6-triene-9,11-diol
• CAS: 93955-70-5
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: IJYOWIYFUHTPRX-GZBOUJLJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  13.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 2-exo-7-anti-Hydroxybenzonorborn-5-ene 在 吡啶 作用下， 以0.041 g的产率得到2-exo-7-anti-Diacetoxybenzonorborn-5-ene
  参考文献：
  名称：

  Sonawane, H. R.; Sethi, S. C.; Merchant, S. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1984, vol. 23, # 10, p. 934 - 939

  摘要：

  DOI：
• 作为产物：
  描述：

  2-exo-7-anti-Diacetoxybenzonorborn-5-ene 在 氨 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以83%的产率得到2-exo-7-anti-Hydroxybenzonorborn-5-ene
  参考文献：
  名称：

  Functionalization of Benzonorbornadiene: High-Temperature Bromination and Electrochemical Oxidation

  摘要：

  The electrophilic addition of bromine to benzonorbornadiene (1) at 10 degrees C led in high yield to the formation of 2-exo-7-anti-dibromide 2. However, high-temperature bromination in decalin at 150 degrees C resulted in the formation of five products, 2-6, consisting of non-rearranged and rearranged products in a ratio of 8:2. Conducting the bromination reaction in the presence of a free radical inhibitor like 2,4,6-tri-tert-butylphenol suppressed the formation of the non-rearranged products. This very strongly supports the assumption that there is a competition between radical and ionic reactions. Anodic oxidation of benzonorbornadiene was investigated. Electrolysis of benzonorbornadiene in different solvents resulted in the formation of 2,7-disubstituted benzonorborn-5-ene derivatives, 8-11, in good yields.

  DOI：

  10.1021/jo00101a011