diethyl (S)-2-phenylsuccinate | 34861-81-9

• 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: diethyl (S)-2-phenylsuccinate
• 英文别名: diethyl (2S)-2-phenylbutanedioate
• CAS: 34861-81-9
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: JVQDNCKPHSZFSO-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 海关编码：
  2917399090

反应信息

• 作为产物：
  描述：

  ethyl 2-iodo-4,4-dimethoxybut-2-enoate 在 四(三苯基膦)钯 、 (S)-5-benzyl-2-mesityl-6,6-dimethyl-5,6-dihydro-8H-[1,2,4]triazolo[3,4-c][1,4]oxazin-2-ium tetrafluoroborate 、 3,4-bis((3,5-bis(trifluoromethyl)phenyl)amino)cyclobut-3-ene-1,2-dione 、 potassium carbonate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 44.0h， 生成 diethyl (S)-2-phenylsuccinate
  参考文献：
  名称：

  Enantioselective β-Protonation by a Cooperative Catalysis Strategy

  摘要：

  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.

  DOI：

  10.1021/jacs.5b02887

文献信息

• Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates
  作者：Xiaolei Ji、Chaoren Shen、Xinxin Tian、Kaiwu Dong

  DOI：10.1021/acs.orglett.1c03361

  日期：2021.11.5

  A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity

  开发了钯催化的 α-芳基丙烯酸与 CO 和醇的不对称加氢酯化反应，以中等收率和高ee值制备了多种手性 α-取代琥珀酸酯。反应过程的动力学曲线表明，烯烃底物首先进行加氢酯化，然后与醇进行酯化。通过密度泛函理论计算阐明了对映选择性的起源。
• Catalytic, Enantioselective β-Protonation through a Cooperative Activation Strategy
  作者：Michael H. Wang、David Barsoum、C. Benjamin Schwamb、Daniel T. Cohen、Brian C. Goess、Matthias Riedrich、Audrey Chan、Brooks E. Maki、Rama K. Mishra、Karl A. Scheidt

  DOI：10.1021/acs.joc.7b00334

  日期：2017.5.5

  only feasible, but also adaptable to a kinetic resolution of secondary alcohols through NHC-catalyzed acylation. In-depth analysis of this process determined that careful catalyst and solvent pairing is critical for optimal yield and selectivity; proper choice of nonpolar solvent provided improved yield through suppression of an oxidative side reaction, while employment of a cooperative catalytic approach

  通过有机催化均烯酸酯方法对NHC催化的不饱和醛向饱和酯的转化已进行了深入研究。利用独特的“ Umpolung ”介导的β质子化，该过程已经从用于均烯酸酯反应性的测试台发展为用于不对称催化的更广泛的平台。受到我们成功使用β质子化过程从具有良好E / Z的艾纳尔中产生enals的启发选择性，我们的早期研究发现该反应的不对称变化不仅可行，而且还可以通过NHC催化的酰化反应适应仲醇的动力学拆分。对这一过程的深入分析表明，仔细的催化剂和溶剂配对对于获得最佳收率和选择性至关重要。非极性溶剂的适当选择提供通过氧化副反应的抑制提高的产量，而就业合作催化方法通过包含氢键供体助催化剂的显著提高对映选择性。
• Preparation of Chiral 3-Arylpyrrolidines via the Enantioselective 1,4-Addition of Arylboronic Acids to Fumaric Esters Catalyzed by Rh(I)/Chiral Diene Complexes
  作者：Yu-Chiang, Chung、Damodar Janmanchi、Hsyueh-Liang Wu

  DOI：10.1021/ol300980k

  日期：2012.6.1

  A highly efficient rhodium-catalyzed protocol for the preparation of 2-arylsuccinic esters and 3-arylpyrrolidines of high optical purity has been achieved. In the presence of 1 mol % of a chiral diene/Rh(I) catalyst, asymmetric addition of various arylboronic acids to di-fert-butyl fumarate (3c) provides the corresponding adducts in up to 99% yield and 94 -> 99.5% ee. Excellent enantioselectivities were also observed in the regio- and enantioselective conjugate addition of phenylboronic acid (4a) to compound 3e.
• Wren; Williams, Journal of the Chemical Society, 1916, vol. 109, p. 580
  作者：Wren、Williams

  DOI：——

  日期：——
• 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.