2,3-exo-cis-Dibromobenzonorborn-5-ene | 23537-86-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 2,3-exo-cis-Dibromobenzonorborn-5-ene
• 英文别名: exo-cis-2,3-Dibrom-benzonorbornen；(1R,8S,9S,10R)-9,10-dibromotricyclo[6.2.1.02,7]undeca-2,4,6-triene
• CAS: 23537-86-2
• 化学式: C₁₁H₁₀Br₂
• 分子量: 302.008
• InChiKey: UGOBXGMGPCCRHH-DTIDVZRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 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：

  2,3-exo-cis-Dibromobenzonorborn-5-ene 以93%的产率得到2-exo-7-syn-Dibromobenzonorborn-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
• 作为产物：
  描述：

  1,4-二氢-1,4-甲桥萘 在 1,2-二溴四氯乙烷 作用下， 以 四氯化碳 为溶剂， 生成 2,3-exo-cis-Dibromobenzonorborn-5-ene
  参考文献：
  名称：

  syn-7-Bromobenzonorbornadiene. Synthesis and solvolytic reactivity

  摘要：

  DOI：

  10.1021/ja01028a046

文献信息

• Nucleophilic substitution of bromonorbornenes and derivatives by electron transfer reactions
  作者：Karina F. Crespo Andrada、Lucas E. Peisino、Murat Güney、Arif Daştan、Adriana B. Pierini

  DOI：10.1039/c2ob26768c

  日期：——

  The photoinitiated substitution reactions of anti-7-bromobenzonorbornadiene (5), its syn isomer 6, exo–anti-13-bromobenzocyclobutanorbornene (7), syn-7-bromonorbornene (8) and bromonorbornane (9) with Me3Sn− and Ph2P− anions, in liquid ammonia, are here informed to occur with good yields of substitution. The stereochemical outcome is discussed in terms of calculations with the B3LYP functional and

  的光引发取代反应的反-7- bromobenzonorbornadiene（5），其顺式异构体6，外切-反-13- bromobenzocyclobutanorbornene（7），顺式-7- bromonorbornene（8）和bromonorbornane（9）与我3的Sn -且Ph 2 P -告知液态氨中的阴离子以良好的取代收率发生。根据B3LYP功能和6-31 + G *基集的计算结果讨论了立体化学结果。通过PCM模型将溶剂作为连续体包含在内。还介绍了成对的底物对给定阴离子的实验相对化学反应性。
• Dastan Arif, Demir Uemit, Balci Metin, J. Org. Chem, 59 (1994) N 22, S 6534-6538
  作者：Dastan Arif, Demir Uemit, Balci Metin

  DOI：——

  日期：——
• syn-7-Bromobenzonorbornadiene. Synthesis and solvolytic reactivity
  作者：James W. Wilt、Philip J. Chenier

  DOI：10.1021/ja01028a046

  日期：1968.12
• Functionalization of Benzonorbornadiene: High-Temperature Bromination and Electrochemical Oxidation
  作者：Arif Dastan、Umit Demir、Metin Balci

  DOI：10.1021/jo00101a011

  日期：1994.11

  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.