ethyl 3-(1,3-benzodioxol-5-yl)-2-benzyl-3-oxopropanoate | 1190081-73-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: ethyl 3-(1,3-benzodioxol-5-yl)-2-benzyl-3-oxopropanoate
• CAS: 1190081-73-2
• 化学式: C₁₉H₁₈O₅
• 分子量: 326.349
• InChiKey: YNPMIGYVUKCBAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  碘苯 、 ethyl 2-(benzo[d][1,3]dioxol-5-yl(hydroxy)methyl)acrylate 在 [5-Cl-2-{(4-Cl-phenyl)-[(E)-HO-imino]methyl}phenyl-PdCl]2 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到ethyl 3-(1,3-benzodioxol-5-yl)-2-benzyl-3-oxopropanoate
  参考文献：
  名称：

  Nájera oxime-derived palladacycles catalyze intermolecular Heck reaction with Morita–Baylis–Hillman adducts. An improved and highly efficient synthesis of α-benzyl-β-ketoesters

  摘要：

  An improved and highly efficient synthesis of several alpha-benzyl-beta-ketoesters from Morita-Baylis-Hillman adducts is described. These adducts were used as substrates for an intermolecular Heck reaction catalyzed by a Najera oxime-derived palladacycles. These efficient catalytic conditions probed to be very selective providing only the corresponding functionalized beta-ketoesters in high yield with no decarboxylation product. It seems that the method herein described is one of the most efficient for the synthesis of alpha-benzyl-beta-ketoesters. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.06.084

文献信息

• Heck Reaction of Baylis–Hillman Adducts with Iodobenzenes Using a Catalytic Amount of Pd/C under Solvent-Free Conditions
  作者：Cheol Yoon、Hyun-Soo Kim、Sang-Jin Lee、Boram Choi

  DOI：10.1055/s-0032-1316992

  日期：——

  The reaction of Baylis-Hillman adducts with iodobenzenes using commercially available palladium-on-carbon as a catalyst under solvent-free conditions afforded the corresponding coupling products, alpha-benzyl-beta-keto esters, in high to excellent yields. The reactions are very efficient.