(E)-ethyl 4-(3-methoxyphenyl)-2-oxobut-3-enoate | 1160761-50-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-ethyl 4-(3-methoxyphenyl)-2-oxobut-3-enoate
• 英文别名: ethyl (E)-4-(3-methoxyphenyl)-2-oxobut-3-enoate
• CAS: 1160761-50-1
• 化学式: C₁₃H₁₄O₄
• 分子量: 234.252
• InChiKey: ABUFXUPGGGNOIA-BQYQJAHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 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：

  糠醛 、 (E)-ethyl 4-(3-methoxyphenyl)-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， 以96%的产率得到(R)-ethyl 5-(furan-2-yl)-4-(3-methoxyphenyl)-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-甲氧基苯甲醛 在 盐酸 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 4.17h， 生成 (E)-ethyl 4-(3-methoxyphenyl)-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

• Palladium-Catalyzed Asymmetric Formal [3+2] Cycloaddition of Vinyl Cyclopropanes and β,γ-Unsaturated α-Keto Esters: An Effective Route to Highly Functionalized Cyclopentanes
  作者：Liang-yong Mei、Yin Wei、Qin Xu、Min Shi

  DOI：10.1021/om300896z

  日期：2012.11.12

  Palladium-catalyzed asymmetric formal [3+2] cycloaddition of vinyl cyclopropanes and β,γ-unsaturated α-keto esters proceeded smoothly in the presence of chiral imidazoline–phosphine ligands to give the corresponding highly functionalized cyclopentanes in good yields along with high diastereo- and enantioselectivities under mild conditions.

  在手性咪唑啉-膦配体的存在下，钯催化的乙烯基环丙烷和β，γ-不饱和α-酮酯的不对称形式[3 + 2]环加成反应顺利进行，从而得到相应的高度官能化的环戊烷，并具有较高的非对映体-收率。和温和条件下的对映选择性。
• 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.