2-(4-氯苯基)-4H-1,3-恶唑-5-酮 | 22887-53-2

• 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: 2-(4-氯苯基)-4H-1,3-恶唑-5-酮
• 英文名称: 2-(4-Chlorphenyl)-4,5-dihydro-1,3-oxazol-5-on
• 英文别名: 2-(4-chloro-phenyl)-4H-oxazol-5-one；2-(4-Chlor-phenyl)-4H-oxazol-5-on；5(4H)-Oxazolone, 2-(4-chlorophenyl)-；2-(4-chlorophenyl)-4H-1,3-oxazol-5-one
• CAS: 22887-53-2
• 化学式: C₉H₆ClNO₂
• 分子量: 195.605
• InChiKey: QMUVAOXAHGUJGC-UHFFFAOYSA-N

物化性质

• 熔点：
  127 °C
• 沸点：
  278.3±42.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  2-(4-氯苯基)-4H-1,3-恶唑-5-酮 在 hydroxide 作用下， 生成 (4-氯苯甲酰基氨基)-乙酸
  参考文献：
  名称：

  Structure-reactivity studies on the equilibrium reaction between phenolate ions and 2-aryloxazolin-5-ones: data consistent with a concerted acyl-group-transfer mechanism

  摘要：

  DOI：

  10.1021/ja00542a028
• 作为产物：
  描述：

  (4-Chloro-benzoylamino)-acetic acid 4-nitro-phenyl ester 在 hydroxide 作用下， 生成 2-(4-氯苯基)-4H-1,3-恶唑-5-酮
  参考文献：
  名称：

  Structure-reactivity studies on the equilibrium reaction between phenolate ions and 2-aryloxazolin-5-ones: data consistent with a concerted acyl-group-transfer mechanism

  摘要：

  DOI：

  10.1021/ja00542a028

文献信息

• Catalytic Asymmetric Synthesis of <i>anti</i>-α,β-Diamino Acid Derivatives
  作者：Sanae Izumi、Yusuke Kobayashi、Yoshiji Takemoto

  DOI：10.1021/acs.orglett.5b03666

  日期：2016.2.19

  A novel approach to chiral anti-α,β-diamino acid derivatives through tandem orthogonal organocatalysis has been developed. Chiral phosphoric acid catalysts control the chemo-, regio-, and stereoselective addition of hydroxylamines to alkylideneoxazolones, while a phosphine catalyst promotes the isomerization of Z- alkylideneoxazolones to the more reactive E- alkylideneoxazolones.

  开发了一种通过串联正交有机催化合成手性抗-α，β-二氨基酸衍生物的新方法。手性磷酸催化剂控制羟胺向亚烷基恶唑啉酮的化学，区域和立体选择性加成，而磷化氢催化剂则促进Z-亚烷基恶唑酮向反应性更高的E-亚烷基恶唑酮的异构化。
• Skeletal Reconstruction of 3-Alkylidenepyrrolidines to Azepines Enabled by Pd-Catalyzed C–N Bond Cleavage
  作者：Licheng Wu、Tong Wang、Chenyang Gao、Wenyi Huang、Jingping Qu、Yifeng Chen

  DOI：10.1021/acscatal.1c00130

  日期：2021.2.5

  Pd-catalyzed C–N bond cleavage strategy for the cycloaddition of pyrrolidines with azlactones or butenolides to construct the azepines. Leverage of the readily accessible 3-alkylidenepyrrolidine can serve as an effective precursor for zwitterionic salts. The in situ formation of an allyl-palladium intermediate through the cleavage of inert, cyclic C–N bonds leads to a cascade [5 + 2] cycloaddition, which allows

  在本文中，我们报道了吡咯烷与丁二酸内酯或丁烯内酯的环加成反应的钯催化C–N键裂解策略，以构建氮杂基。容易获得的3-亚烷基亚吡咯烷的杠杆作用可作为两性离子盐的有效前体。通过裂解惰性环状C–N键原位形成烯丙基钯中间体会导致级联[5 + 2]环加成反应，从而可以多样化合成具有良好官能团耐受性和100％原子的氮杂骨架经济。
• Formal [4+2] Cycloaddition of Vinyl Benzoxazinones with Oxazol‐5‐(4 <i>H</i> )‐Ones for Diastereoselective Construction of 3,4‐Disubstituted Dihydro‐2(1 <i>H</i> )‐Quinolinones
  作者：Hong‐Wu Zhao、Wan‐Qiu Ding、Jia‐Ming Guo、Li‐Ru Wang、Xiu‐Qing Song、Xiao‐Zu Fan、Zhe Tang、Hui‐Hui Wu、Xiao‐Fan Bi

  DOI：10.1002/adsc.201900560

  日期：2019.9.3

  Catalyzed by Pd2(dba)3.CHCl3 and PPh3, the formal [4+2] cycloaddition between vinyl benzoxazinones and oxazol‐5‐(4H)‐ones proceeded readily and delivered 3,4‐disubstituted dihydro‐2(1H)‐quinolinones in the reasonable chemical yields with excellent diastereoselectivities. The relative stereochemical configuration of the title products was unambiguously characterized with the use of X‐ray diffraction

  由Pd 2（dba）3催化。CHCl 3和PPh 3，是乙烯基苯并恶嗪酮与恶唑-5-（4 H）-酮之间的正式[4 + 2]环加成反应，可以轻松进行，并在合理的化学反应条件下提供了3,4-二取代的二氢-2（1 H）-喹啉酮。产生具有优异的非对映选择性的产物。使用X射线衍射分析可明确表征标题产物的相对立体化学构型。
• Synthetic scope and DFT analysis of the chiral binap–gold(I) complex-catalyzed 1,3-dipolar cycloaddition of azlactones with alkenes
  作者：María Martín-Rodríguez、Luis M Castelló、Carmen Nájera、José M Sansano、Olatz Larrañaga、Abel de Cózar、Fernando P Cossío

  DOI：10.3762/bjoc.9.280

  日期：——

  The 1,3-dipolar cycloaddition between glycine-derived azlactones with maleimides is efficiently catalyzed by the dimeric chiral complex [(S_a)-Binap·AuTFA]₂. The alanine-derived oxazolone only reacts with tert-butyl acrylate giving anomalous regiochemistry, which is explained and supported by Natural Resonance Theory and Nucleus Independent Chemical Shifts calculations. The origin of the high enantiodiscrimination observed with maleimides and tert-butyl acrylate is analyzed using DFT computed at M06/Lanl2dz//ONIOM(b3lyp/Lanl2dz:UFF) level. Several applications of these cycloadducts in the synthesis of new proline derivatives with a 2,5-trans-arrangement and in the preparation of complex fused polycyclic molecules are described.

  1,3-二极环加成反应是由二聚手性复合物[(Sa)-Binap·AuTFA]2高效催化的，该反应涉及甘氨酸衍生的氮内酯与马来酰亚胺的反应。丙氨酸衍生的氧代噁唑酮只与叔丁基丙烯酸酯发生反应，产生异常的区域化学反应，这一现象通过自然共振理论和核独立化学位移计算得到解释和支持。观察到的与马来酰亚胺和叔丁基丙烯酸酯的高对映选择性的起源是通过使用M06/Lanl2dz//ONIOM(b3lyp/Lanl2dz:UFF)水平的密度泛函理论进行分析。描述了这些环加成产物在合成新的脯氨酸衍生物中的几种应用，这些衍生物具有2,5-trans排列，以及在制备复杂的融合多环分子中的应用。
• Enantioselective 1,3-Dipolar Cycloadditions of Azlactones and Electrophilic Alkenes Catalyzed by Dimeric BinapAuTFA Complexes
  作者：Carmen Nájera、José Sansano、María Martín-Rodríguez

  DOI：10.1055/s-0030-1260334

  日期：2012.1

  This work has been supported by the Spanish Ministerio de Ciencia e Innovacion (MICINN) [Consolider INGENIO 2010 CSD2007-00006, CTQ2007-62771/BQU, CTQ2010-20387, FEDER, Generalitat Valenciana (PROMETEO/2009/039)], and by the University of Alicante. M.M.-R. also thanks MICINN for a grant.

  这项工作得到了西班牙国家科学与创新部长 (MICINN) [Consolider INGENIO 2010 CSD2007-00006, CTQ2007-62771/BQU, CTQ2010-20387, FEDER, Generalitat Valenciana (PROMETEO/3909) 的支持]阿利坎特大学。MM-R。还要感谢 MICINN 的资助。