methyl 3-(1,3-benzodioxol-5-yl)-2-(4-methoxybenzyl)-3-oxopropanoate | 1190081-74-3

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: methyl 3-(1,3-benzodioxol-5-yl)-2-(4-methoxybenzyl)-3-oxopropanoate
• CAS: 1190081-74-3
• 化学式: C₁₉H₁₈O₆
• 分子量: 342.348
• InChiKey: DQAGDEXLSYUMKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  71.06
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-碘苯甲醚 、 methyl 3-hydroxy-2-methylene-3-[(3,4-methylenedioxy)phenyl]propanoate 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84%的产率得到methyl 3-(1,3-benzodioxol-5-yl)-2-(4-methoxybenzyl)-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