2-phenyl-4-thiophen-2-ylmethyl-4H-oxazol-5-one | 221071-23-4

• 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-phenyl-4-thiophen-2-ylmethyl-4H-oxazol-5-one
• 英文别名: 2-phenyl-4-(thiophen-2-ylmethyl)oxazol-5(4H)-one；2-phenyl-4-(2-thiophenylmethyl)oxazol-j5(4H)-one；2-phenyl-4-(thiophen-2-ylmethyl)-4H-1,3-oxazol-5-one
• CAS: 221071-23-4
• 化学式: C₁₄H₁₁NO₂S
• 分子量: 257.313
• InChiKey: RSVPDBQNMFZDHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-4-thiophen-2-ylmethyl-4H-oxazol-5-one 在 Candida antarctica B lipase 、 水 作用下， 以 乙腈 为溶剂， 反应 72.0h， 生成 2-benzoylamino-3-[2]thienyl-propionic acid
  参考文献：
  名称：

  Polyclonal antibodies: a cheap and efficient tool for screening of enantioselective catalysts

  摘要：

  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。

  DOI：

  10.1039/c2cc31312j
• 作为产物：
  描述：

  3-(2-噻吩基)-DL-丙氨酸 在 乙酸酐 作用下， 生成 2-phenyl-4-thiophen-2-ylmethyl-4H-oxazol-5-one
  参考文献：
  名称：

  Ring opening with kinetic resolution of azlactones by Ti-TADDOLates

  摘要：

  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.

  DOI：

  10.1016/s0040-4020(98)01064-3

文献信息

• Enantioselective Addition of Azlactones to Ethylene Sulfonyl Fluoride via Dual Catalysis
  作者：Dong-yu Zhu、Xue-jing Zhang、Ming Yan

  DOI：10.1021/acs.orglett.1c01193

  日期：2021.6.4

  Enantioselective conjugate addition of azlactones to ethylene sulfonyl fluoride has been achieved via the cooperative catalysis with (DHQD)2PHAL and a hydrogen-bond donor (HBD). This approach furnishes a facile access to a range of structurally diverse azlactone sulfonyl fluoride derivatives with good to excellent yields and enantioselectivities. The combination of azlactone and sulfonyl fluoride group

  通过与 (DHQD) 2 PHAL 和氢键供体 (HBD)的协同催化，实现了吖内酯与亚乙基磺酰氟的对映选择性共轭加成。这种方法可以轻松获得一系列结构多样的吖内酯磺酰氟衍生物，具有良好的收率和对映选择性。吖内酯和磺酰氟基团的组合为药物发现产生了有价值的非天然 α-季铵酸衍生物。
• 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'。
• 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，
• Construction of α,β-Diamino Diacid Derivatives with Adjacent Acyclic Tetrasubstituted Stereocenters
  作者：Feng Zhou、Qi-Long Hu、Ke-Qiang Hou、Albert S. C. Chan、Xiao-Feng Xiong

  DOI：10.1021/acs.joc.2c00950

  日期：2022.7.1

  A convenient strategy for the diastereoselective synthesis of α,β-diamino diacid derivatives bearing congested vicinal acyclic tetrasubstituted stereocenters via catalytic Mannich-type reactions of azlactones and 2-aminoacrylates was established. A diverse set of α,β-diamino diacid derivatives were synthesized in good to excellent yields and diastereoselectivities. Good enantioselectivity (up to 98:2

  建立了通过吖内酯和 2-氨基丙烯酸酯的催化曼尼希型反应非对映选择性合成具有拥挤的邻位无环四取代立体中心的 α,β-二氨基二酸衍生物的简便策略。以良好至优异的产率和非对映选择性合成了多种 α,β-二氨基二酸衍生物。通过在随后的不对称研究中使用催化剂 (DHQD) 2 PHAL实现了良好的对映选择性（高达 98:2 er） 。
• Asymmetric [3+2]-cyclization of α-imino amide surrogates to construct 3,4-diaminopyrrolidine-2,5-diones
  作者：Peiran Ruan、Cefei Zhang、Jin Wu、Fengnan Xiao、Yongyan Zhang、Qingfa Tan、Zhishan Su、Xiaoming Feng、Xiaohua Liu

  DOI：10.1039/d3cc01203d

  日期：——

  Using novel α-imino amide surrogates and chiral guanidine, diaminopyrrolidines derivatives could be obtained with good results and versatile application value. The role of guanidine was demonstrated by DFT calculations.

  利用新型α-亚氨基酰胺代用品和手性胍，获得了二氨基吡咯烷衍生物，结果良好，具有广泛的应用价值。DFT 计算证明了胍的作用。