4-naphthalen-1-ylmethyl-2-phenyl-4H-oxazol-5-one | 149832-10-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-naphthalen-1-ylmethyl-2-phenyl-4H-oxazol-5-one
• 英文别名: 4-(1-naphthalenylmethyl)-2-phenyloxazol-5(4H)-one；4-(naphthalen-1-ylmethyl)-2-phenyloxazol-5(4H)-one；4-(naphthalen-1-ylmethyl)-2-phenyl-4H-1,3-oxazol-5-one
• CAS: 149832-10-0
• 化学式: C₂₀H₁₅NO₂
• 分子量: 301.345
• InChiKey: YWABZYSGCDQXOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-naphthalen-1-ylmethyl-2-phenyl-4H-oxazol-5-one 在 C₄₁H₃₀N₄O₂ 、 氢溴酸 、 溶剂黄146 、 苯甲酸 作用下， 以 氯仿 为溶剂， 反应 7.0h， 生成 3-(1-萘基)-L-丙氨酸盐酸盐
  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
• 作为产物：
  描述：

  3-(1-萘基)-L-丙氨酸 在 溶剂黄146 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 4-naphthalen-1-ylmethyl-2-phenyl-4H-oxazol-5-one
  参考文献：
  名称：

  Peptide-Catalyzed Conversion of Racemic Oxazol-5(4H)-ones into Enantiomerically Enriched α-Amino Acid Derivatives

  摘要：

  We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

  DOI：

  10.1021/jo402828f

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 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。
• Enzymic asymmetric synthesis of .alpha.-amino acids. Enantioselective cleavage of 4-substituted oxazolin-5-ones and thiazolin-5-ones
  作者：Joyce Z. Crich、Rosario Brieva、Peer Marquart、Rui Lin Gu、Steffen Flemming、Charles J. Sih

  DOI：10.1021/jo00064a010

  日期：1993.6

  A general enzymatic asymmetric synthesis of L-alpha-amino acids has been developed. This method entails the use of the Pseudomonas cepacia lipase (P-30) to catalyze the enantioselective methanolysis of a variety of 4-substituted 2-phenyloxazolin-5-one derivatives in a nonpolar organic solvent to furnish optically-active N-benzoyl-L-alpha-amino acid methyl esters (ee = 66-98%), which in turn is subjected to a protease-catalyzed kinetic resolution yielding enantiomerically-pure N-benzoyl-L-alpha-amino acids. This synergistic coupling of two enzymes allows the ready preparation of L-alpha-amino acids of high enantiopurity in yields greater than 50%, an inherent advantage over conventional resolution procedures. Two proteases were found to catalyze the enantioselective hydrolysis of a variety of 4-substituted 2-phenylthiazolin-5-one derivatives to give N-(thiobenzoyl)-L-alpha-amino acids of high optical purity.