3-(m-tolyl)isoxazol-5(4H)-one | 861328-94-1

• 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: 3-(m-tolyl)isoxazol-5(4H)-one
• 英文别名: 3-(3-methylphenyl)-4H-1,2-oxazol-5-one
• CAS: 861328-94-1
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: PCWWGLYFGKBQJU-UHFFFAOYSA-N

物化性质

• 沸点：
  275.2±33.0 °C(Predicted)
• 密度：
  1.21±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：
  0.2
• 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：

  3-(m-tolyl)isoxazol-5(4H)-one 在 正丁基锂 、 三氯氧磷 作用下， 以 乙醚 为溶剂， 生成 (3-Azepan-1-yl-propyl)-benzo[1,3]dioxol-5-ylmethyl-(3-m-tolyl-isoxazol-5-yl)-amine
  参考文献：
  名称：

  Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)

  摘要：

  The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50S of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(01)00745-4
• 作为产物：
  描述：

  (3-甲基苯甲酰基)乙酸乙酯 在 盐酸羟胺 、 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 生成 3-(m-tolyl)isoxazol-5(4H)-one
  参考文献：
  名称：

  通过Rh催化级联C–H活化/环化3-芳基异恶唑酮与环2-重氮-1,3-二酮，构建异恶唑酮融合的菲啶

  摘要：

  描述了Rh（III）催化的3-芳基-5-异恶唑酮与环2-重氮-1,3-二酮的级联C–H活化/分子内环化，导致异恶唑[2,3- f ]的形成菲啶骨架。该协议的特征是同时一锅形成两个新的C–C / C–N键和一个杂环，具有中等至良好的产率，并具有良好的官能团相容性。适于大规模合成和进一步转化。

  DOI：

  10.1039/d0ob02310h

文献信息

• Rh(III)-Catalyzed Regioselective Annulations of 3-Arylisoxazolones and 3-Aryl-1,4,2-dioxazol-5-ones with Propargyl Alcohols: Access to 4-Arylisoquinolines and 4-Arylisoquinolones
  作者：Tong-Tong Wang、Hai-Shan Jin、Man-Man Cao、Ru-Bing Wang、Li-Ming Zhao

  DOI：10.1021/acs.orglett.1c02049

  日期：2021.8.6

  The Rh(III)-catalyzed dual directing group assisted C–H activation/annulation of 3-arylisoxazolones with propargyl alcohols has been developed, which expands the application scope of isoxazolones in organic synthesis. This protocol also worked well with 3-aryl-1,4,2-dioxazol-5-ones to produce synthetically and biologically important 4-arylisoquinolones.

  开发了Rh(III)催化的双导向基团辅助C-H活化/环化3-芳基异恶唑酮与炔丙醇，扩大了异恶唑酮在有机合成中的应用范围。该协议还适用于 3-芳基-1,4,2-二恶唑-5-酮，以生产具有合成和生物学重要性的 4-芳基异喹诺酮。
• Rh(III)-Catalyzed [4 + 2] Annulation of 3-Aryl-5-isoxazolone with Maleimides or Maleic Ester
  作者：Ting Wan、Chao Pi、Yangjie Wu、Xiuling Cui

  DOI：10.1021/acs.orglett.0c02283

  日期：2020.8.21

  The Rh(III)-catalyzed [4 + 2] annulation of 3-aryl-5-isoxazolones with maleimides or maleic ester has been developed, which gives synthetically important 3,4-dihydroisoquinoline derivatives in good to excellent yields. This facile protocol can tolerate a variety of functional groups, and CO2 was produced as the predominant byproduct. Notably, a C–C bond and a C–N bond were formed simultaneously. This

  已经开发了Rh（III）催化的3-芳基-5-异恶唑酮与马来酰亚胺或顺丁烯二酸酯的[4 + 2]环化反应，从而以良好的产率获得了重要的合成3,4-二氢异喹啉衍生物。这种简便的方案可以耐受各种官能团，并且产生了CO 2作为主要副产物。值得注意的是，CC键和CN键是同时形成的。该协议可以轻松扩展。
• Organocatalytic Asymmetric One-Pot Sequential Conjugate Addition/Dearomative Fluorination: Synthesis of Chiral Fluorinated Isoxazol-5(4<i>H</i>)-ones
  作者：Wen-Ting Meng、Yan Zheng、Jing Nie、Heng-Ying Xiong、Jun-An Ma

  DOI：10.1021/jo302419e

  日期：2013.1.18

  A facile one-pot sequential conjugate addition/dearomative fluorination transformation of isoxazol-5(4H)-ones with nitroolefins and N-fluorobenzenesulfonimide (NFSI) has been developed. By using a bifunctional chiral tertiary amino-thiourea catalyst, a series of chiral fluorinated isoxazol-5(4H)-ones containing one fluorine-substituted quarternary stereocenter were obtained in high yields with high

  已经开发了一种方便的一锅连续的异恶唑-5（4 H）-酮与硝基烯烃和N-氟苯磺酰亚胺（NFSI）的顺序共轭加成/脱氟化法转化的方法。通过使用双功能手性叔氨基-硫脲催化剂，可以高收率获得具有高对映异构和非对映异构选择性的一系列含有一个氟取代的叔叔立体中心的手性氟化异恶唑-5（4 H）-。加合物的进一步转化可以得到具有三个连续立体中心的异恶唑烷-5-一衍生物。
• Construction of isoxazolone-fused phenanthridines <i>via</i> Rh-catalyzed cascade C–H activation/cyclization of 3-arylisoxazolones with cyclic 2-diazo-1,3-diketones
  作者：Wangcheng Hu、Xinwei He、Tongtong Zhou、Youpeng Zuo、Shiwen Zhang、Tingting Yang、Yongjia Shang

  DOI：10.1039/d0ob02310h

  日期：——

  A Rh(III)-catalyzed cascade C–H activation/intramolecular cyclization of 3-aryl-5-isoxazolones with cyclic 2-diazo-1,3-diketones was described, leading to the formation of isoxazolo[2,3-f]phenanthridine skeletons. The protocol features the simultaneous one-pot formation of two new C–C/C–N bonds and one heterocycle in moderate-to-good yields with good functional group compatibility. It is amenable to

  描述了Rh（III）催化的3-芳基-5-异恶唑酮与环2-重氮-1,3-二酮的级联C–H活化/分子内环化，导致异恶唑[2,3- f ]的形成菲啶骨架。该协议的特征是同时一锅形成两个新的C–C / C–N键和一个杂环，具有中等至良好的产率，并具有良好的官能团相容性。适于大规模合成和进一步转化。
• Discovery of a nonpeptidic small molecule antagonist of the human platelet thrombin receptor (PAR-1)
  作者：Philippe G Nantermet、James C Barrow、George F Lundell、Janetta M Pellicore、Kenneth E Rittle、MaryBeth Young、Roger M Freidinger、Thomas M Connolly、Cindra Condra、Jerzy Karczewski、Rodney A Bednar、Stanley L Gaul、Robert J Gould、Kris Prendergast、Harold G Selnick

  DOI：10.1016/s0960-894x(01)00745-4

  日期：2002.2

  The synthesis and biological evaluation of a series of nonpeptidic small molecule antagonists of the human platelet thrombin receptor (PAR-1) are described. Optimization of the 5-amino-3-arylisoxazole lead resulted in an approximate 100-fold increase in potency. The most potent of these compounds (54) inhibits platelet activation with IC50S of 90 nM against the thrombin receptor agonist peptide (TRAP) and 510 nM against thrombin as the agonist. Further, antagonist 54 fully blocks platelet aggregation stimulated by 1 nM thrombin for 10 min. (C) 2002 Published by Elsevier Science Ltd.