4-ethyl 1-methyl 2-phenylsuccinate | 132545-36-9

• 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: 4-ethyl 1-methyl 2-phenylsuccinate
• 英文别名: 1-Methyl-4-ethyl 2-phenylsuccinate；4-O-ethyl 1-O-methyl 2-phenylbutanedioate
• CAS: 132545-36-9
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: NLGKQUAICLWDDR-UHFFFAOYSA-N

物化性质

• 沸点：
  317.8±22.0 °C(Predicted)
• 密度：
  1.111±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  苯乙酸甲酯 在 palladium on activated charcoal 、 4-乙酰氨基苯磺酰叠氮 、 氢气 、 dirhodium cofactor covalently linked to prolyl oligopeptidase scaffold containing a genetically encoded azidophenylalanine (Z) residue at position 477 mutant 5-G 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 sodium bromide 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 46.5h， 生成 4-ethyl 1-methyl 2-phenylsuccinate
  参考文献：
  名称：

  用于重氮偶联级联反应的工程铱人造金属酶**

  摘要：

  人工金属酶 (ArMs) 通常用于控制催化反应的立体选择性，但控制化学选择性仍然具有挑战性。在这项研究中，我们设计了一种 dirhodium ArM 来催化重氮交叉偶联形成烯烃，该烯烃在一锅级联反应中被烯烃还原酶还原为具有高对映选择性（通常 > 99% ee）的烷烃. 级联反应所需的大量蛋白质和小分子成分对 ArM 催化的影响很小。Arm 的定向进化提高了产量和E / Z对各种底物的选择性，这转化为级联反应产率。ArM 变体的 MD 模拟用于了解辅助因子对 ArM 构象动力学的结构作用。这些结果突出了 ArMs 控制催化剂立体选择性和化学选择性的能力，以实现在复杂介质中的反应，否则会导致不希望的副反应。

  DOI：

  10.1002/anie.202107982

文献信息

• Diastereo- and Enantioselective Synthesis of Fluorine Motifs with Two Contiguous Stereogenic Centers
  作者：Sudipta Ponra、Wangchuk Rabten、Jianping Yang、Haibo Wu、Sutthichat Kerdphon、Pher G. Andersson

  DOI：10.1021/jacs.8b08778

  日期：2018.10.24

  motifs, in particular, chiral fluorine molecules with two contiguous stereogenic centers, has attracted much interest in research due to the limited number of methods available for their preparation. Herein, we report an atom-economical and highly stereoselective synthesis of chiral fluorine molecules with two contiguous stereogenic centers via azabicyclo iridium-oxazoline-phosphine-catalyzed hydrogenation

  手性氟的合成，特别是具有两个连续立体中心的手性氟分子，由于其制备方法的数量有限，引起了人们对研究的极大兴趣。在此，我们报告了通过氮杂双环铱-恶唑啉-膦催化氢化容易获得的氟乙烯，以原子经济和高度立体选择性合成具有两个连续立体中心的手性氟分子。发现具有各种官能团的各种芳香族、脂肪族和杂环系统与反应相容，并提供非常理想的产物，作为具有优异对映选择性的单一非对映异构体。
• 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。
• Enantioselective β-Protonation by a Cooperative Catalysis Strategy
  作者：Michael H. Wang、Daniel T. Cohen、C. Benjamin Schwamb、Rama K. Mishra、Karl A. Scheidt

  DOI：10.1021/jacs.5b02887

  日期：2015.5.13

  An enantioselective N-hetetoeyclic carbene (NHC)-catalyzed beta-protonation through the orchestration of three distinct organocatalysts has been developed. This cooperative catalyst system enhances both yield and selectivity, compared to only the NHC-catalyzed process. This new method allows for the,efficient conversion of a large scope of aryl-oxobutenoates to highly enantioenriched succinate derivatives and demonstrates the benefits of combining different activation modes in organocatalysis.
• Highly specific fragmentation processes of isomeric mixed esters of phenylsuccinic acid under electron impact
  作者：I. Vidavsky、A. Mandelbaum、T. Tamiri、S. Zitrin

  DOI：10.1002/oms.1210260420

  日期：1991.4

  AbstractIsomeric mixed dialkyl phenylsuccinates, PhCH(COOR)CH2COOR′, undergo a highly specific elimination of ROH under electron impact. A deuterium‐labelling study showed that the hydrogen atom from the benzylic position 2 is abstracted in this process. These results suggest the occurrence of a ‘hidden’ hydrogen migration of the benzylic hydrogen atom to the carbonylic oxygen of the remote ester group, followed by the elimination of ROH from the adjacent ester group with the involvement of that hydrogen. Alkoxyl group migrations resulting in the formation of [PhCHOR]+ and [PhCHOR′]+ ions are less specific, although the migration of the remote R′O˙ is significantly preferred in all the pairs of isomers examined. Mechanisms are suggested for the formation of the two ions.