(E)-2-Acetoxymethyl-but-2-enoic acid methyl ester

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (E)-2-Acetoxymethyl-but-2-enoic acid methyl ester
• 英文别名: methyl (E)-2-(acetyloxymethyl)but-2-enoate
• 化学式: C₈H₁₂O₄
• 分子量: 172.181
• InChiKey: RJBMWLBQNSGSLQ-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2-Acetoxymethyl-but-2-enoic acid methyl ester 、 1-甲基吲哚 在 bis(acetylacetonato)palladium(II) 、 三苯基膦 作用下， 以 溶剂黄146 为溶剂， 反应 3.25h， 以51%的产率得到3-(2'-methoxycarbonyl-1'-buten-3'-yl)-1-methylindole
  参考文献：
  名称：

  Palladium-Catalyzed Functionalization of Indoles with 2-Acetoxymethyl-Substituted Electron-Deficient Alkenes

  摘要：

  New functionalizations of indoles via palladium-catalyzed reaction of indoles and 2-acetoxymethyl-substituted electron-deficient alkenes are reported. It was found that for N-protected indoles the reaction proceeded smoothly in the presence of 5 mol % of Pd(acac)(2) and 10 mol % of PPh3 at 80 degrees C in HOAc, while for N-unprotected indoles, the reaction was carried out by using 5 mol % of Pd(dba)(2) or 2.5 mol % of Pd-2(dba)(3), CHCl3 with 10 mol % of 2,2'-bipyridine as the catalyst in toluene. This strategy allows the selective installation of electron-deficient olefin functionality at the 3-position of indoles, which might be difficult to obtain by other methods and can be further elaborated.

  DOI：

  10.1021/jo061546s