2-Methyl-2-(2-phenyl-allyl)-malonic acid dimethyl ester | 313708-71-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-Methyl-2-(2-phenyl-allyl)-malonic acid dimethyl ester
• 英文别名: Propanedioic acid, methyl(2-phenyl-2-propenyl)-, dimethyl ester；dimethyl 2-methyl-2-(2-phenylprop-2-enyl)propanedioate
• CAS: 313708-71-3
• 化学式: C₁₅H₁₈O₄
• 分子量: 262.306
• InChiKey: CVEWSSDADCNCAW-UHFFFAOYSA-N

物化性质

• 沸点：
  344.4±42.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  1.0
• 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：

  甲基丙二酸二甲酯 在 四(三苯基膦)钯 、 sodium hydride 、 lithium chloride 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.25h， 生成 2-Methyl-2-(2-phenyl-allyl)-malonic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of Stereodefined Polysubstituted Olefins. 1. Sequential Intermolecular Reactions Involving Selective, Stepwise Insertion of Pd(0) into Allylic and Vinylic Halide Bonds. The Stereoselective Synthesis of Disubstituted Olefins¹

  摘要：

  Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin beta -D-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.

  DOI：

  10.1021/jo001045l

文献信息

• Differentiating allylic and vinylic leaving groups for Pd catalysis. The use of vinyl iodide to facilitate room temperature activation of a vinyl CX bond in the presence of allyl carbonate
  作者：Michael G. Organ、Elena A. Arvanitis、Anita Villani、Yvette Majkut、Stephen Hynes

  DOI：10.1016/s0040-4039(03)00881-5

  日期：2003.6

  Ionization of allylic, stabilized leaving groups by Pd catalysis is a very facile process at or below room temperature, whereas oxidative addition of many vinyl or aryl CX bonds requires heating. There are only a handful of examples in the literature where a vinyl leaving group can be activated in a competitive fashion in the presence of a suitable allylic one. In this report a series of polyfunctional

  在室温或室温以下，通过Pd催化使烯丙基稳定的离去基团电离是一个非常容易的过程，而许多乙烯基或芳基CX键的氧化加成则需要加热。在文献中只有少数的例子，其中乙烯基离去基团可以在合适的烯丙基的存在下以竞争的方式被活化。在该报告中，已经构造了一系列多官能烯烃结构单元，其允许在高活性烯丙基离去基团存在的情况下选择性地和常规地活化乙烯基卤化物。这种区别仅取决于所涉及的离去基团的键强度，并且没有温度依赖性来区分这两个过程。