2-benzoylamino-3-[2]thienyl-propionic acid | 69935-10-0

• 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-benzoylamino-3-[2]thienyl-propionic acid
• 英文别名: 2-Benzoylamino-3-[2]thienyl-propionsaeure；N-benzoyl-β-2-thienyl-DL-alanin；2-Benzamido-3-thiophen-2-ylpropanoic acid
• CAS: 69935-10-0；83396-74-1；83396-75-2
• 化学式: C₁₄H₁₃NO₃S
• 分子量: 275.328
• InChiKey: XWGRCHUPNVPDDU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  94.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-benzoylamino-3-[2]thienyl-propionic acid 在 4-二甲氨基吡啶 、 三乙胺 、 N,N'-二环己基碳二亚胺 、 三苯基膦 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 27.25h， 生成 2-benzoylamino-2-(thien-2-yl)methylpenta-3,4-dienoic acid methyl ester
  参考文献：
  名称：

  Heterocyclic α-Alkylidene Cyclopentenones Obtained via a Pauson−Khand Reaction of Amino Acid Derived Allenynes. A Scope and Limitation Study Directed toward the Preparation of a Tricyclic Pyrrole Library

  摘要：

  [GRAPHICS]The synthesis of a novel class of tricyclic pyrroles has been accomplished by using a Pauson-Khand/Stetter/Paal-Knorr reaction sequence. Full details of the Pauson-Khand reaction of amino acid tethered allenynes 4a-e and 9a-d are disclosed. The study of this reaction led to the discovery of an unprecedented substituent effect on the diastereoselectivity of the MO(CO)(6) mediated allenic Pauson-Khand reaction. It was found that amino acid tethered allenynes with aromatic side chains afford alpha-alkylidene cyclopentenones with the opposite diastereoselectivity compared to those with aliphatic side chains. This effect has been attributed to complexation of the metal mediator to the aromatic ring in the substrate. Furthermore, an isomerization of one of the diastereomers of the a-alkylidene cyclopentenones was encountered, leading to eventual decomposition. The stable diastereomers were found to react well in the Stetter reaction leading to 1,4-diketones that were converted to pyrroles. The observation that the first generation of 2-alkyl-substituted pyrroles was unstable led to a second generation of 2-carboxamide pyrroles with sufficient stability for biological tests which are in progress.

  DOI：

  10.1021/jo0481607
• 作为产物：
  描述：

  2-Benzoylamino-3-thiophen-2-yl-propionic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-benzoylamino-3-[2]thienyl-propionic acid
  参考文献：
  名称：

  含1,1'-联萘单元的N，N-二甲基-4-氨基吡啶手性衍生物对内酯的动力学动力学：酰胺基的重要性

  摘要：

  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'。

  DOI：

  10.1021/acs.orglett.8b01960

文献信息

• Polyclonal antibodies: a cheap and efficient tool for screening of enantioselective catalysts
  作者：Cristian Macovei、Paola Vicennati、Julia Quinton、Marie-Claire Nevers、Hervé Volland、Christophe Créminon、Frédéric Taran

  DOI：10.1039/c2cc31312j

  日期：——

  Enantioselective polyclonal antibodies have been produced and characterized to develop a high-throughput screening method for lipase activity fingerprinting, with a view to the enantioselective hydrolysis of azlactones.

  已生产和表征了对映选择性多克隆抗体，以开发一种用于脂肪酶活性指纹图谱的高通量筛选方法，旨在对对映选择性水解氮杂内酯。
• 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，
• Ring opening with kinetic resolution of azlactones by Ti-TADDOLates
  作者：Konstanze Gottwald、Dieter Seebach

  DOI：10.1016/s0040-4020(98)01064-3

  日期：1999.1

  The kinetic resolution of azlactones by the Lewis-acid-mediated transfer of an isopropoxide ligand from the chiral ligand sphere of Ti-TADDOLate is described. The reactions proceed with in-situ racemization of the starting material to afford highly enantiomerically enriched N-benzoyl-amino acid isopropylesters (er > 95:5 after recrystallization). The absolute configuration of the major enantiomer of N-benzoyl-phenylalanine isopropyl ester and its analogs with other aromatic substituents was shown to be (S)-(+) when the (R,R)-Ti-TADDOLate was employed. Only benzyl-substituted azlactones can be opened enantioselectively by the method described here. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 399. Synthesis of β-2-thienylalanine and of β-2-thienylethylamine
  作者：George Barger、Alexander P. T. Easson

  DOI：10.1039/jr9380002100

  日期：——
• Yuan; Li, Journal of the Chinese Chemical Society, 1937, vol. 5, p. 214,217
  作者：Yuan、Li

  DOI：——

  日期：——