1,1',6,6',7,7'-hexamethoxy-5,5'-diisopropyl-3,3'-bis(bromomethyl)-2,2'-binaphthalene | 139583-64-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,1',6,6',7,7'-hexamethoxy-5,5'-diisopropyl-3,3'-bis(bromomethyl)-2,2'-binaphthalene
• 英文别名: 3-(Bromomethyl)-2-[3-(bromomethyl)-1,6,7-trimethoxy-5-propan-2-ylnaphthalen-2-yl]-1,6,7-trimethoxy-5-propan-2-ylnaphthalene
• CAS: 139583-64-5
• 化学式: C₃₄H₄₀Br₂O₆
• 分子量: 704.496
• InChiKey: SNZLHNNBLRPTAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  202-204 °C
• 沸点：
  701.8±60.0 °C(Predicted)
• 密度：
  1.339±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  42
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  5,5'-diisopropyl-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene 在 pyridinium hydrobromide perbromide 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以70%的产率得到1,1',6,6',7,7'-hexamethoxy-5,5'-diisopropyl-3,3'-bis(bromomethyl)-2,2'-binaphthalene
  参考文献：
  名称：

  Regioselective bromination and fluorination of apogossypol hexamethyl ether

  摘要：

  Apogossypol hexamethyl ether (3) was brominated upon treatment with any of a number of brominating agents. Each reagent gave a different bromo derivative. Thus, the reaction of 3 with bromine in CCl4 with ultrasound irradiation gave 4 in 71% yield. When treated with bromine and iron powder in CCl4 at-5-degrees-C, 3 afforded 5 in 65% yield. The reaction of 3 with pyridinium bromide perbromide in 1,2-dichloroethane at 65-70-degrees-C furnished 6 in 70% yield. Treatment of 3 with NBS in DMF at room temperature afforded 7 in 30% yield. Treatment of 4 and 5 with potassium fluoride and 18-crown-6 in acetonitrile at room temperature furnished 8 and 9, respectively. An attempt to introduce trifluoromethyl groups at the 8 and 8' positions of 4, by treatment with cuprous iodide and sodium trifluoroacetate, failed and gave only 10. Interestingly, but unexpectedly, 11 and 12 were produced upon treating 4 with silver(1) fluoride.

  DOI：

  10.1021/jo00034a024

文献信息

• Regioselective bromination and fluorination of apogossypol hexamethyl ether
  作者：Guidong Zhu、Dehua Chen、Jianhua Huang、Chingsung Chi、Fukuang Liu

  DOI：10.1021/jo00034a024

  日期：1992.4

  Apogossypol hexamethyl ether (3) was brominated upon treatment with any of a number of brominating agents. Each reagent gave a different bromo derivative. Thus, the reaction of 3 with bromine in CCl4 with ultrasound irradiation gave 4 in 71% yield. When treated with bromine and iron powder in CCl4 at-5-degrees-C, 3 afforded 5 in 65% yield. The reaction of 3 with pyridinium bromide perbromide in 1,2-dichloroethane at 65-70-degrees-C furnished 6 in 70% yield. Treatment of 3 with NBS in DMF at room temperature afforded 7 in 30% yield. Treatment of 4 and 5 with potassium fluoride and 18-crown-6 in acetonitrile at room temperature furnished 8 and 9, respectively. An attempt to introduce trifluoromethyl groups at the 8 and 8' positions of 4, by treatment with cuprous iodide and sodium trifluoroacetate, failed and gave only 10. Interestingly, but unexpectedly, 11 and 12 were produced upon treating 4 with silver(1) fluoride.