methyl 2,4-dicarbomethoxy-5-(2'-furyl)-4-heptenoate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: methyl 2,4-dicarbomethoxy-5-(2'-furyl)-4-heptenoate
• 英文别名: trimethyl (E)-4-(furan-2-yl)but-3-ene-1,1,3-tricarboxylate
• 化学式: C₁₄H₁₆O₇
• 分子量: 296.277
• InChiKey: IKDXECMWAVJBIU-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  92
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 2-(acetoxy(furan-2-yl)methyl)acrylate 、 丙二酸二甲酯 在 四(三苯基膦)钯 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到methyl 2,4-dicarbomethoxy-5-(2'-furyl)-4-heptenoate
  参考文献：
  名称：

  Palladium Catalysed Reactions of Baylis-Hillman Products: Synthesis of Some Useful Intermediates

  摘要：

  Acetates derived from Baylis-Hillman products were reacted with sodio dimethyl (or diethyl) malonate under Pd(0) catalysis to form E olefins as the major products. Likewise, the Heck reaction with these acetates as well as with the corresponding alcohols form a variety of useful intermediates which include trisubstituted olefinic compounds and alpha-benzyl beta- keto esters.

  DOI：

  10.1080/00397919808007047

文献信息

• The Synthesis and Some Manipulations of Dialkyl 6-Aryl (or Alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates
  作者：RM Lawrence、P Perlmutter

  DOI：10.1071/ch9960839

  日期：——

  A new, one-pot annulation process, involving conjugate addition of the sodium salts of dimethyl (or dibenzyl ) malonate to alkyl 2-(1- hydroxyalkyl ) propenoates, produces a mixture of dialkyl 6-aryl(or alkyl)-2-oxotetrahydro-2H-pyran-3,5-dicarboxylates. Alkylations of the cis-isomers were found to be highly stereoselective . The ntroduction of unsaturation into these molecules is also described.

  一种新的、一锅法的缩合过程，涉及将二甲基（或二苄基）丙二酸酯的钠盐进行共轭加成到烷基2-(1-羟基烷基)丙烯酸酯中，产生一种二烷基6-芳基（或烷基）-2-氧代四氢-2H-吡喃-3,5-二羧酸酯混合物。发现对顺式异构体的烷基化反应具有高度立体选择性。还介绍了向这些分子引入不饱和度的方法。
• Palladium Catalysed Reactions of Baylis-Hillman Products: Synthesis of Some Useful Intermediates
  作者：R. Kumareswaran、Yashwant D. Vankar

  DOI：10.1080/00397919808007047

  日期：1998.6

  Acetates derived from Baylis-Hillman products were reacted with sodio dimethyl (or diethyl) malonate under Pd(0) catalysis to form E olefins as the major products. Likewise, the Heck reaction with these acetates as well as with the corresponding alcohols form a variety of useful intermediates which include trisubstituted olefinic compounds and alpha-benzyl beta- keto esters.