dimethyl 2-allyl-2-((E)-buta-1,3-dienyl)malonate

• 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: dimethyl 2-allyl-2-((E)-buta-1,3-dienyl)malonate
• 英文别名: dimethyl 2-[(1E)-buta-1,3-dienyl]-2-prop-2-enylpropanedioate
• 化学式: C₁₂H₁₆O₄
• 分子量: 224.257
• InChiKey: AEKZLUDHZRDYIM-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸烯丙酯 、 dimethyl (E)-2-(but-2-en-1-ylidene)malonate 在 lithium hexamethyldisilazane 、 tris-(dibenzylideneacetone)dipalladium(0) 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以82%的产率得到dimethyl 2-allyl-2-((E)-buta-1,3-dienyl)malonate
  参考文献：
  名称：

  Novel Synthesis of Conjugated Dienes Attached to a Quaternary Carbon Center via Pd(0)-Catalyzed Deconjugative Allylation of Alkenylidenemalonates

  摘要：

  Palladium(0)-catalyzed deconjugative allylation of alkenylidenemalonates and alkylidenemalonates was achieved for the first time. Reactions of dimethyl 2-((E)-but-2-enylidene)malonate with various allylic acetates using LHMDS as a base in DMF in the presence of Pd(2)dba(3) (2.5 mol %) and PPh3 (10 mol %) proceeded at room temperature to give the corresponding alpha-allylation products in good yields in a regio- and stereoselective manner. This reaction can also be used for allylation of dimethyl ethylidenemalonate or dimethyl 2-((E)-pent-2-enylidene)malonate and give the desired a-allylation products in good yields.

  DOI：

  10.1021/jo0353334

文献信息

• Novel Synthesis of Conjugated Dienes Attached to a Quaternary Carbon Center via Pd(0)-Catalyzed Deconjugative Allylation of Alkenylidenemalonates
  作者：Yoshihiro Sato、Yoshihiro Oonishi、Miwako Mori

  DOI：10.1021/jo0353334

  日期：2003.12.1

  Palladium(0)-catalyzed deconjugative allylation of alkenylidenemalonates and alkylidenemalonates was achieved for the first time. Reactions of dimethyl 2-((E)-but-2-enylidene)malonate with various allylic acetates using LHMDS as a base in DMF in the presence of Pd(2)dba(3) (2.5 mol %) and PPh3 (10 mol %) proceeded at room temperature to give the corresponding alpha-allylation products in good yields in a regio- and stereoselective manner. This reaction can also be used for allylation of dimethyl ethylidenemalonate or dimethyl 2-((E)-pent-2-enylidene)malonate and give the desired a-allylation products in good yields.