(E)-ethyl 4-(furan-3-yl)-2-oxobut-3-enoate | 1327274-48-5

• 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)-ethyl 4-(furan-3-yl)-2-oxobut-3-enoate
• 英文别名: Ethyl 4-(furan-3-yl)-2-oxobut-3-enoate；ethyl (E)-4-(furan-3-yl)-2-oxobut-3-enoate
• CAS: 1327274-48-5
• 化学式: C₁₀H₁₀O₄
• 分子量: 194.187
• InChiKey: PPPUYPNDVJPGOL-ONEGZZNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  56.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  糠醛 、 (E)-ethyl 4-(furan-3-yl)-2-oxobut-3-enoate 在 (5R,7R)-7-fluoro-5-isopropyl-2-(perfluorophenyl)-6,7-dihydro-5H-pyrrolo[2,1c][1,2,4]triazol-2-ium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 生成 (R)-ethyl 5-(furan-2-yl)-4-(furan-3-yl)-2,5-dioxopentanoate 、 (S)-ethyl 5-(furan-2-yl)-4-(furan-3-yl)-2,5-dioxopentanoate
  参考文献：
  名称：

  Highly Enantioselective Intermolecular Stetter Reactions of β-Aryl Acceptors: α-Ketoester Moiety as Handle for Activation and Synthetic Manipulations

  摘要：

  The use of beta,gamma-unsaturated-alpha-ketoesters in the intermolecular Stetter reaction furnishes 1,2,5-tricarbonyl compounds in high yield and excellent enantioselectivity. The alpha,delta-diketoesters generated using this methodology serve as useful synthetic building blocks via chemo- and diastereoselective transformations.

  DOI：

  10.1021/ol202040b
• 作为产物：
  描述：

  3-糠醛 在 盐酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 4.17h， 生成 (E)-ethyl 4-(furan-3-yl)-2-oxobut-3-enoate
  参考文献：
  名称：

  Highly Enantioselective Intermolecular Stetter Reactions of β-Aryl Acceptors: α-Ketoester Moiety as Handle for Activation and Synthetic Manipulations

  摘要：

  The use of beta,gamma-unsaturated-alpha-ketoesters in the intermolecular Stetter reaction furnishes 1,2,5-tricarbonyl compounds in high yield and excellent enantioselectivity. The alpha,delta-diketoesters generated using this methodology serve as useful synthetic building blocks via chemo- and diastereoselective transformations.

  DOI：

  10.1021/ol202040b

文献信息

• Highly Enantioselective Intermolecular Stetter Reactions of β-Aryl Acceptors: α-Ketoester Moiety as Handle for Activation and Synthetic Manipulations
  作者：Eduardo Sánchez-Larios、Karen Thai、François Bilodeau、Michel Gravel

  DOI：10.1021/ol202040b

  日期：2011.9.16

  The use of beta,gamma-unsaturated-alpha-ketoesters in the intermolecular Stetter reaction furnishes 1,2,5-tricarbonyl compounds in high yield and excellent enantioselectivity. The alpha,delta-diketoesters generated using this methodology serve as useful synthetic building blocks via chemo- and diastereoselective transformations.