N-苯甲酰基苯丙氨酸乙酯 | 64896-35-1

• 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
• 中文名称: N-苯甲酰基苯丙氨酸乙酯
• 英文名称: (R)-2-(N-benzoylamino)-3-phenylpropanoic acid ethyl ester
• 英文别名: N-benzoyl-D-phenylalanine ethyl ester；(R)-ethyl N-benzoyl-phenylalaninate；N-benzoylethyl phenylalaninate；ethyl (2R)-2-benzamido-3-phenylpropanoate
• CAS: 64896-35-1
• 化学式: C₁₈H₁₉NO₃
• 分子量: 297.354
• InChiKey: WTVXOKSBXDTJEM-MRXNPFEDSA-N

物化性质

• 沸点：
  505.1±43.0 °C(Predicted)
• 密度：
  1.142±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ethyl (Z)-2-benzamido-3-phenylacrylate 在 rhodium(I)-(S,S)-skewphos complexes 氢气 作用下， 以 四氢呋喃 为溶剂， 生成 N-苯甲酰基苯丙氨酸乙酯
  参考文献：
  名称：

  Asymmetric synthesis. Asymmetric catalytic hydrogenation using chiral chelating six-membered ring diphosphines

  摘要：

  DOI：

  10.1021/ja00399a023

文献信息

• Dynamic Kinetic Resolution of Azlactones by a Chiral <i>N</i>,<i>N</i>-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups
  作者：Hiroki Mandai、Kohei Hongo、Takuma Fujiwara、Kazuki Fujii、Koichi Mitsudo、Seiji Suga

  DOI：10.1021/acs.orglett.8b01960

  日期：2018.8.17

  resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3′-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide α-amino acid derivatives with good to high enantiomeric ratios (er’s). A multigram-scale reaction (2.5 g) for the

  在苯甲酸和基于联萘基的N，N -4-二甲基氨基吡啶（DMAP）衍生物1i的联苯胺基的3,3'-位置上具有两个酰胺基的情况下，开发了内酯的动态动力学拆分（DKR）。该反应在宽范围的氮杂内酯下顺利进行，以提供具有良好至高对映体比率（er's）的α-氨基酸衍生物。还证实了对a内酯2d的DKR的数克规模反应（2.5g），并且将所得产物转化为非天然α-氨基酸6d'。
• Highly Enantioselective Decarboxylative Protonation of α-Aminomalonates Mediated by Thiourea <i>Cinchona</i> Alkaloid Derivatives:  Access to Both Enantiomers of Cyclic and Acyclic α-Aminoacids
  作者：Mukkanti Amere、Marie-Claire Lasne、Jacques Rouden

  DOI：10.1021/ol070712v

  日期：2007.7.1

  Thiourea derived cinchona alkaloids promote the asymmetric decarboxylative protonation of cyclic, acyclic, or bicyclic alpha-aminomalonate hemiesters under mild and metal-free conditions to afford enantioenriched aminoesters in high yields and enantioselectivities up to 93%. Both enantiomers of the aminoesters have been synthesized with the same selectivity when using organic base 3 and its pseudoenantiomer

  硫脲衍生的金鸡纳生物碱可在温和且无金属的条件下促进环状，无环或双环α-氨基丙二酸酯半酯的不对称脱羧质子化，从而以高收率和高达93％的对映选择性提供对映体富集的氨基酯。当使用有机碱3及其衍生自奎宁的假对映体6时，已以相同的选择性合成了氨基酯的两种对映体。
• Dynamic Kinetic Resolution of Azlactones by Bifunctional Thioureas with α‑Trifluoromethyl or Methyl Groups
  作者：Marcos Hernández-Rodríguez、Eddy I. Jiménez、Margarita Cantú-Reyes、Miguel Flores-Ramos、Carlos A. Román-Chavarría、Howard Díaz-Salazar

  DOI：10.1055/a-1892-9911

  日期：2022.10

  The asymmetric ring opening of azlactones via dynamic kinetic resolution (DKR) is investigated by contrasting thioureas incorporating 1-arylethyl substituents against their more acidic trifluoromethylated analogs. All the catalysts under study outperform Takemoto’s thiourea because of the inclusion of an additional chiral center. However, the difference in yield and selectivity between the fluorinated

  通过将含有 1-芳乙基取代基的硫脲与其更具酸性的三氟甲基化类似物进行对比，研究了通过动态动力学拆分 (DKR) 的 azlactones 的不对称开环。由于包含一个额外的手性中心，所有正在研究的催化剂都优于 Takemoto 的硫脲。然而，氟化和非氟化催化剂之间的产率和选择性差异很小。我们通过分析计算的过渡态来解释这一观察结果。我们的研究结果表明，与 1-芳乙基连接的 NH 与苄氧基离子中带负电的氧之间的氢键 (HB) 在 HB 网络中最长，而铵基与同一氧原子之间的 HB 是最短。因此，
• Polymer-supported thioamide-derived cinchona alkaloids as efficient organocatalysts for the enantioselective decarboxylative protonation
  作者：Bénédicte Lepoittevin、Jérôme Baudoux、Doriann Bray、Aimar Gonzalo-Barquero、Jacques Rouden

  DOI：10.1016/j.reactfunctpolym.2023.105731

  日期：2023.11

  thioamide derivative was synthesized by conventional radical polymerization. The copolymers were tested as homogeneous supported organocatalysts in the enantioselective decarboxylative protonation (EDP) of α-aminomalonate hemiesters giving access to α-amino acids under very mild conditions. These macromolecular catalysts could be prepared on a large scale and outperformed their unsupported analogues providing

  通过常规自由基聚合合成了基于苯乙烯和可聚合辛可尼丁硫代酰胺衍生物的新型共聚物。该共聚物在α-氨基丙二酸半酯的对映选择性脱羧质子化（EDP）中作为均相负载有机催化剂进行了测试，从而在非常温和的条件下获得α-氨基酸。这些大分子催化剂可以大规模制备，并且性能优于其无载体类似物，以高产率和对映选择性提供所需的产物。此外，进行的回收实验显示出良好的对映选择性。
• An eco-benign and highly efficient procedure for N-acylation catalyzed by heteropolyanion-based ionic liquids using carboxylic acid under solvent-free conditions
  作者：Zhikai Chen、Renzhong Fu、Wen Chai、Hao Zheng、Lin Sun、Qiang Lu、Rongxin Yuan

  DOI：10.1016/j.tet.2014.02.042

  日期：2014.4

  An eco-benign and highly efficient route for N-acylation of amines has been developed by treating amines with corresponding carboxylic acids in the presence of 2 mol % of heteropolyanion-based ionic liquids as catalysts under solvent-free conditions. This practical reaction could tolerate a wide range of substrates. Thus, various N-acylation products including N-acyl alpha-amino acid derivatives were obtained in moderate to excellent yields at 70 degrees C to 120 degrees C. Moreover, recycling studies revealed that heteropolyanion-based ionic liquids were easily reusable for this N-acylation. This method provides a green and much improved protocol over the existing methods.(c) 2014 Elsevier Ltd. All rights reserved.