6,6',7,7'-tetramethoxy-5,5'-diisopropyl-8,8'-dibromo-3,3'-bis(bromomethyl)dinaphtho<2,1-b:2',1'-d>furan | 139583-62-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: 6,6',7,7'-tetramethoxy-5,5'-diisopropyl-8,8'-dibromo-3,3'-bis(bromomethyl)dinaphtho<2,1-b:2',1'-d>furan
• 英文别名: 9,15-Dibromo-3,21-bis(bromomethyl)-7,8,16,17-tetramethoxy-6,18-di(propan-2-yl)-12-oxapentacyclo[11.8.0.02,11.05,10.014,19]henicosa-1(13),2(11),3,5(10),6,8,14(19),15,17,20-decaene
• CAS: 139583-62-3
• 化学式: C₃₂H₃₂Br₄O₅
• 分子量: 816.219
• InChiKey: JPLVIEVQQYXSFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,6',7,7'-tetramethoxy-5,5'-diisopropyl-8,8'-dibromo-3,3'-bis(bromomethyl)dinaphtho<2,1-b:2',1'-d>furan 在 sodium sulfide 作用下， 以 水 、 叔丁醇 、 苯 为溶剂， 反应 10.0h， 以50%的产率得到1,12-dibromo-2,3,10,11-tetramethoxy-4,9-diisopropyl-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
• 作为产物：
  描述：

  5,5'-diisopropyl-1,1',6,6',7,7'-hexamethoxy-3,3'-dimethyl-2,2'-binaphthalene 在 溴 作用下， 以 四氯化碳 为溶剂， 反应 10.0h， 以71%的产率得到6,6',7,7'-tetramethoxy-5,5'-diisopropyl-8,8'-dibromo-3,3'-bis(bromomethyl)dinaphtho<2,1-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