1,12-dibromo-2,3,10,11-tetramethoxy-4,9-diisopropyl-14-oxo-6,7-(methanoxymethano)dinaphtho<1,2-b:2',1'-d>furan | 139606-47-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 1,12-dibromo-2,3,10,11-tetramethoxy-4,9-diisopropyl-14-oxo-6,7-(methanoxymethano)dinaphtho<1,2-b:2',1'-d>furan
• 英文别名: 1,12-dibromo-2,3,10,11-tetramethoxy-4,9-diisopropyl-14-oxo-6,7-(methanoxymethano)dinaphtho[1,2-b:2',1'-d]furan；3,19-Dibromo-4,5,17,18-tetramethoxy-6,16-di(propan-2-yl)-11,24-dioxahexacyclo[19.2.1.02,7.09,23.013,22.015,20]tetracosa-1,3,5,7,9(23),13,15(20),16,18,21-decaen-10-one
• CAS: 139606-47-6
• 化学式: C₃₂H₃₀Br₂O₇
• 分子量: 686.394
• InChiKey: GMJFZSSBAKRGBO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  41
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  76.4
• 氢给体数：
  0
• 氢受体数：
  7

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 溴 、 silver fluoride 作用下， 以 四氯化碳 、 乙二醇二甲醚 为溶剂， 反应 20.0h， 生成 1,12-dibromo-2,3,10,11-tetramethoxy-4,9-diisopropyl-14-oxo-6,7-(methanoxymethano)dinaphtho<1,2-b:2',1'-d>furan
  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.