1-(5-(tert-butoxycarbonyl)-2-methyl-4,5-dihydrofuran-3-yl)ethanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 1-(5-(tert-butoxycarbonyl)-2-methyl-4,5-dihydrofuran-3-yl)ethanone
• 英文别名: 1-(5-(tert-butoxy)-2-methyl-4,5-dihydrofuran-3-yl)ethanone；1-[5-Methyl-2-[(2-methylpropan-2-yl)oxy]-2,3-dihydrofuran-4-yl]ethanone；1-[5-methyl-2-[(2-methylpropan-2-yl)oxy]-2,3-dihydrofuran-4-yl]ethanone
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: HRXXZOQUOUVDEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2Z)-3-偶氮基-4-氧代-2-戊烯-2-醇 、 叔丁基乙烯基醚 在 tris(triphenylphosphine)ruthenium(II) chloride 、 1-butyl-3-methylimidazolium tetrafluoroborate 作用下， 以 甲苯 为溶剂， 反应 0.33h， 以87%的产率得到1-(5-(tert-butoxycarbonyl)-2-methyl-4,5-dihydrofuran-3-yl)ethanone
  参考文献：
  名称：

  钌（II）催化的[3 + 2]环或无环重氮二羰基化合物与烯烃的环加成反应，高效一锅合成多取代的二氢呋喃

  摘要：

  AbstractRuthenium(II)‐phosphine complexes‐catalyzed [3+2] cycloadditions were conducted to synthesize a variety of dihydrofurans by reactions of cyclic or acyclic diazodicarbonyl compounds with olefins. This method represents a direct and efficient one‐pot synthesis for multi‐substituted dihydrofurans under mild reaction conditions with an excellent regioselectivity. Furthermore, to reduce reaction times and increase yields of dihydrofurans, microwave‐assisted tris(triphenylphosphine)ruthenium(II) chloride/ 1‐butyl‐3‐methylimidazolium tetrafluoroborate {Ru(PPh3)3Cl2/[Bmim]BF4}‐catalyzed reactions were also developed. The synthesized dihydrofurans can be readily converted into biologically interesting tetrahydroindoles.magnified image

  DOI：

  10.1002/adsc.201300245