2-methoxycarbonyl-3-phenyl-succinic acid dimethyl ester

• 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: 2-methoxycarbonyl-3-phenyl-succinic acid dimethyl ester
• 英文别名: 2-phenyl-ethane-1,1,2-tricarboxylic acid trimethyl ester；2-Phenyl-aethan-1,1,2-tricarbonsaeure-trimethylester；Trimethyl 2-phenylethane-1,1,2-tricarboxylate；trimethyl 2-phenylethane-1,1,2-tricarboxylate
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: VUCVTTZLWHCEFB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-cyano-2-hydroxy-2-phenyl-succinic acid dimethyl ester 在 sodium amalgam 、 sodium methylate 作用下， 生成 2-methoxycarbonyl-3-phenyl-succinic acid dimethyl ester
  参考文献：
  名称：

  Kohler, Corson, Journal of the American Chemical Society, 1923, vol. 45, p. 1983

  摘要：

  DOI：

文献信息

• Electrochemical carboxylation of cinnamate esters in MeCN
  作者：Huan Wang、Kai Zhang、Ying-Zi Liu、Mei-Yu Lin、Jia-Xing Lu

  DOI：10.1016/j.tet.2007.10.104

  日期：2008.1

  of cinnamate esters has been carried out by cathodic reduction of CC bond in an undivided cell equipped with Mg sacrificial anode and using MeCN saturated with CO2 as solvent. The yields and the ratio of mono- and dicarboxylic acids are strongly affected by various factors: cathodic material, current, charge, and temperature. The highest yield (78.9%) was obtained starting from ethyl cinnamate. Cyclic

  肉桂酸酯的电化学羧化反应是通过在配备Mg牺牲阳极的未分隔电池中，以饱和CO 2的MeCN作为溶剂，将CC键阴极还原而实现的。一元羧酸和二元羧酸的收率和比例受多种因素的强烈影响：阴极材料，电流，电荷和温度。从肉桂酸乙酯开始获得最高产率（78.9％）。已测量了循环伏安图，并提出了反应途径。
• Cu/PCy ₃ ‐Catalyzed Formal Carbene Insertion into Electron‐Deficient C−H Bonds
  作者：Yuan‐Yuan Ren、Hong‐Xiang Mao、Meng‐Yang Hu、Shou‐Fei Zhu、Qi‐Lin Zhou

  DOI：10.1002/cctc.202000684

  日期：2020.9.4

  A carbene insertion into electron‐deficient C−H bonds of 1,3‐diesters, β‐ketoesters, β‐ketonitriles, and malononitriles was realized by using CuCN/PCy3 as the catalyst. The reaction provides a straightforward approach to the synthetically important multi‐substituted succinic acid derivatives. A plausible reaction mechanism with cyclopropanation/ring opening as key steps was proposed based on control

  通过使用CuCN / PCy 3作为催化剂，将卡宾插入到1,3-二酯，β-酮酸酯，β-酮腈和丙二腈的电子不足的CH键中。该反应为合成上重要的多取代琥珀酸衍生物提供了一种直接方法。在控制实验的基础上，提出了以环丙烷化/开环为关键步骤的合理反应机理。
• A C_sp³–C_sp³ Bond Forming Reductive Condensation of α-Keto Esters and Enolizable Carbon Pronucleophiles
  作者：Wei Zhao、Darla M. Fink、Carolyn A. Labutta、Alexander T. Radosevich

  DOI：10.1021/ol401276b

  日期：2013.6.21

  functionalized unsymmetrical 1,4-dicarbonyl structural motifs by a phosphorus(III)-mediated reductive condensation of α-keto esters and enolizable carbon pronucleophiles is described. The reaction, which is initiated by Kukhtin–Ramirez addition of commercially available tris(dimethylamino)phosphine to the α-keto ester substrate, proceeds rapidly under mild conditions.

  描述了通过磷（III）介导的α-酮酸酯与可烯醇化的碳亲核试剂的还原缩合制备致密功能化的不对称1,4-二羰基结构基序。该反应是由Kukhtin-Ramirez将可商购获得的三（二甲基氨基）膦加到α-酮酯底物上引发的，在温和条件下迅速进行。