2-(trifluoromethyl)-3-(chloromethyl)-5-methylfuran

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-(trifluoromethyl)-3-(chloromethyl)-5-methylfuran
• 英文别名: 3-(Chloromethyl)-5-methyl-2-(trifluoromethyl)furan；3-(chloromethyl)-5-methyl-2-(trifluoromethyl)furan
• 化学式: C₇H₆ClF₃O
• 分子量: 198.572
• InChiKey: BJMHDNQGIVZJIR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(trifluoromethyl)-3-(chloromethyl)-5-methylfuran 、 sodium diethyl phosphite 以 苯 为溶剂， 反应 16.0h， 以69%的产率得到diethyl [2-(trifluoromethyl)-5-methylfur-3-yl]methanephosphonate
  参考文献：
  名称：

  Synthesis and Wittig Reaction of Formylated (Trifluoromethylfuryl)methanephosphonates

  摘要：

  Methods of synthesis of 4-functionalyzed (5-trifluoromethylfur-2-yl)methanephosphonates and (5-methyl-2-trifluoromethylfur-3-yl)methanephosphonate are developed. Their formylation with ethyl formate in the presence of sodium foil is studied. Spectral characteristics of tautomers of obtained derivatives of phosphonoacetic aldehyde are evaluated. It is shown that interaction of obtained formyl derivatives with ethoxycarbonylmethylenetriphenylphosphorane regardless of the structure of the furan fragment leads to 4-furylsubstituted alkyl 4-(diethoxyphosphoryl)but-3-enoate, the abnormal product of Wittig reaction.

  DOI：

  10.1134/s1070363218020093
• 作为产物：
  描述：

  [5-甲基-2-(三氟甲基)-3-呋喃基]甲醇 在 吡啶 、 氯化亚砜 作用下， 以 乙酸乙酯 为溶剂， 反应 24.0h， 以48%的产率得到2-(trifluoromethyl)-3-(chloromethyl)-5-methylfuran
  参考文献：
  名称：

  Synthesis and Wittig Reaction of Formylated (Trifluoromethylfuryl)methanephosphonates

  摘要：

  Methods of synthesis of 4-functionalyzed (5-trifluoromethylfur-2-yl)methanephosphonates and (5-methyl-2-trifluoromethylfur-3-yl)methanephosphonate are developed. Their formylation with ethyl formate in the presence of sodium foil is studied. Spectral characteristics of tautomers of obtained derivatives of phosphonoacetic aldehyde are evaluated. It is shown that interaction of obtained formyl derivatives with ethoxycarbonylmethylenetriphenylphosphorane regardless of the structure of the furan fragment leads to 4-furylsubstituted alkyl 4-(diethoxyphosphoryl)but-3-enoate, the abnormal product of Wittig reaction.

  DOI：

  10.1134/s1070363218020093