4,9-dimethoxy-7,7-bis(trifluoromethyl)-6,7-dihydro-5H-furo[3,2-g]chroman-5-ol | 609346-86-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4,9-dimethoxy-7,7-bis(trifluoromethyl)-6,7-dihydro-5H-furo[3,2-g]chroman-5-ol
• 英文别名: 6,7-Dihydro-4,9-dimethoxy-7,7-bis(trifluoromethyl)-5H-furo-[3,2-G]-chromene-5-OL；4,9-dimethoxy-7,7-bis(trifluoromethyl)-5,6-dihydrofuro[3,2-g]chromen-5-ol
• CAS: 609346-86-3
• 化学式: C₁₅H₁₂F₆O₅
• 分子量: 386.248
• InChiKey: VKMPLNZEGVKWOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4,9-dimethoxy-7,7-bis(trifluoromethyl)-6,7-dihydro-5H-furo[3,2-g]chroman-5-ol 在 对甲苯磺酸 作用下， 以 xylene 为溶剂， 反应 2.0h， 以73%的产率得到4,9-dimethoxy-7,7-bis(trifluoromethyl)-7H-furo[3,2-g]chromene
  参考文献：
  名称：

  Regioselective Nucleophilic 1,4-Trifluoromethylation of 2-Polyfluoroalkylchromones with (Trifluoromethyl)trimethylsilane. Synthesis of Fluorinated Analogs of Natural 2,2-Dimethylchroman-4-ones and 2,2-Dimethylchromenes

  摘要：

  Reactions of 2-polyfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(polyfluoroalkyl)chroman-4-ones with high regioselectivity and good yields after acid hydrolysis. Oxidation of 6-methyl-2,2-bis(trifluoromethyl)chroman-4-one with a mixture of K2S2O8 and CuSO4 in aqueous acetonitrile leads to fluorinated analogues of natural lactarochromal and the corresponding acid. Reduction of substituted 2,2-bis(trifluoromethyl)chroman-4-one with sodium borohydride in methanol and subsequent dehydration of chromanols in refluxing xylene in the presence of p-toluene sulfonic acid gives 2,2-bis(trifluoromethyl)chromenes, which are fluorinated analogues of natural precocenes.

  DOI：

  10.1021/jo034591y
• 作为产物：
  描述：

  7-(trifluoromethyl)norkhellin 在 盐酸 、 sodium tetrahydroborate 、 四甲基氟化铵 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.25h， 生成 4,9-dimethoxy-7,7-bis(trifluoromethyl)-6,7-dihydro-5H-furo[3,2-g]chroman-5-ol
  参考文献：
  名称：

  Regioselective Nucleophilic 1,4-Trifluoromethylation of 2-Polyfluoroalkylchromones with (Trifluoromethyl)trimethylsilane. Synthesis of Fluorinated Analogs of Natural 2,2-Dimethylchroman-4-ones and 2,2-Dimethylchromenes

  摘要：

  Reactions of 2-polyfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(polyfluoroalkyl)chroman-4-ones with high regioselectivity and good yields after acid hydrolysis. Oxidation of 6-methyl-2,2-bis(trifluoromethyl)chroman-4-one with a mixture of K2S2O8 and CuSO4 in aqueous acetonitrile leads to fluorinated analogues of natural lactarochromal and the corresponding acid. Reduction of substituted 2,2-bis(trifluoromethyl)chroman-4-one with sodium borohydride in methanol and subsequent dehydration of chromanols in refluxing xylene in the presence of p-toluene sulfonic acid gives 2,2-bis(trifluoromethyl)chromenes, which are fluorinated analogues of natural precocenes.

  DOI：

  10.1021/jo034591y

文献信息

• Regioselective Nucleophilic 1,4-Trifluoromethylation of 2-Polyfluoroalkylchromones with (Trifluoromethyl)trimethylsilane. Synthesis of Fluorinated Analogs of Natural 2,2-Dimethylchroman-4-ones and 2,2-Dimethylchromenes
  作者：Vyacheslav Ya. Sosnovskikh、Boris I. Usachev、Dmitri V. Sevenard、Gerd-Volker Röschenthaler

  DOI：10.1021/jo034591y

  日期：2003.10.1

  Reactions of 2-polyfluoroalkylchromones with (perfluoroalkyl)trimethylsilanes proceed as a 1,4-nucleophilic perfluoroalkylation to give 2,2-bis(polyfluoroalkyl)chroman-4-ones with high regioselectivity and good yields after acid hydrolysis. Oxidation of 6-methyl-2,2-bis(trifluoromethyl)chroman-4-one with a mixture of K2S2O8 and CuSO4 in aqueous acetonitrile leads to fluorinated analogues of natural lactarochromal and the corresponding acid. Reduction of substituted 2,2-bis(trifluoromethyl)chroman-4-one with sodium borohydride in methanol and subsequent dehydration of chromanols in refluxing xylene in the presence of p-toluene sulfonic acid gives 2,2-bis(trifluoromethyl)chromenes, which are fluorinated analogues of natural precocenes.