3-(2-furanyl)-3-methylbutanal | 208241-86-5

• 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: 3-(2-furanyl)-3-methylbutanal
• 英文别名: 3-(Furan-2-yl)-3-methylbutanal
• CAS: 208241-86-5
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: KNLRBSBHSUHKRC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(2-furanyl)-3-methylbutanal 在 nickel dichloride chromium dichloride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 48.0h， 生成 (E)-ethyl 6-(2-furanyl)-4-oxo-6-methyl-2-heptenoate
  参考文献：
  名称：

  Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates

  摘要：

  The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.

  DOI：

  10.1021/jo9721554
• 作为产物：
  描述：

  senecioyl cyanide 在 三氯化铝 、 二异丁基氢化铝 作用下， 以 正己烷 、 甲苯 、 苯 为溶剂， 反应 16.0h， 生成 3-(2-furanyl)-3-methylbutanal
  参考文献：
  名称：

  Substituent Effects in the Intramolecular Diels−Alder Reaction of 6-Furylhexenoates

  摘要：

  The series of furyl enone esters, 4a-c, were synthesized from furan or furfural by straightforward routes. Their thermal intramolecular Diels-Alder reactions to give the tricyclic ketones 5a-c were studied in acetonitrile and toluene at two temperatures and the kinetics of the reactions determined. A comparison of these data with that obtained for the corresponding esters 2 to give the lactones 3 indicates that the rate enhancements seen for the esters (rate of dimethyl 310 times that of monomethyl) are much larger than those seen for the ketones (rate of dimethyl 6.8 times that of monomethyl). Thus, this is additional evidence for the earlier hypothesis that the presence of the oxygen atom in the tether is a factor responsible for the larger than normal rate enhancements.

  DOI：

  10.1021/jo9721554