3-(2-甲基苯基)-4H-1,2-恶唑-5-酮 | 31709-49-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(2-甲基苯基)-4H-1,2-恶唑-5-酮
• 英文名称: 3-(o-tolyl)isoxazol-5(4H)-one
• 英文别名: 3-(2-Methylphenyl)-2-isoxazolin-5-on；3-(o-Tolyl)-Δ²-isoxazolin-5-on；3-o-tolyl-2H-isoxazol-5-one；3-(2-Methylphenyl)-1,2-oxazol-5(4H)-one；3-(2-methylphenyl)-4H-1,2-oxazol-5-one
• CAS: 31709-49-6
• 化学式: C₁₀H₉NO₂
• 分子量: 175.187
• InChiKey: AXZFJDOYBQAHEL-UHFFFAOYSA-N

物化性质

• 沸点：
  269.5±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-(2-甲基苯基)-4H-1,2-恶唑-5-酮 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-o-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：

  1-甲基苯基乙酮 在 盐酸羟胺 、 sodium hydride 、 potassium carbonate 作用下， 以 乙醇 、 水 、 甲苯 为溶剂， 生成 3-(2-甲基苯基)-4H-1,2-恶唑-5-酮
  参考文献：
  名称：

  异恶唑-5-酮与乙烯磺酰氟的区域选择性共轭加成

  摘要：

  已经开发了异恶唑-5-酮与乙烯磺酰氟（ESF）的高度区域选择性共轭加成。在不同碱的存在下，分别获得了具有良好至优异收率的具有磺酰氟基团的N 2-烷基化和C4-烷基化异恶唑-5-酮。与胺和苯酚的进一步转化得到磺酰胺和磺酸盐。异恶唑-5-酮和磺酰氟基团的有趣组合产生了用于药物发现的有价值的产品。

  DOI：

  10.1039/d2ob00737a

文献信息

• 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。
• Atom-Economic Silver-Catalyzed Difunctionalization of the Isocyano Group with Cyclic Oximes: Towards Pyrimidinediones
  作者：Hong-Wen Liang、Zhen Yang、Kun Jiang、Ying Ye、Ye Wei

  DOI：10.1002/anie.201801363

  日期：2018.5.14

  An unprecedented silver‐catalyzed difunctionalization of the isocyano group with cyclic oximes is described. This method allows efficient and atom‐economic assembly of a vast array of structurally novel and interesting pyrimidinediones, and tolerates a range of functionalities. The resulting products can be easily converted into some useful compounds. Furthermore, the method can also be applied for

  描述了前所未有的银催化的异氰酸酯基与环肟的双官能化。这种方法可以高效，原子经济地组装大量结构新颖，有趣的嘧啶二酮，并具有一定的功能范围。所得产物可以容易地转化成一些有用的化合物。此外，该方法还可用于一些生物活性分子的后期修饰。
• 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。
• Difunctionalization of the Isocyano Group: Atom-Economic ­Synthesis of Pyrimidinediones
  作者：Jian Lang、Ye Wei

  DOI：10.1055/s-0037-1610348

  日期：2019.2

  the nitrogen and carbons atoms of the isocyano group would largely enrich the structural diversity of compounds. Herein, we disclosed a silver-catalyzed difunctionalization of the isocyano group with cyclic oximes. This method can generate a great array of structurally novel and interesting pyrimidinediones and features excellent atom economy, good functional group compatibility, and amenability to late-stage

  探索涉及在异氰基的氮和碳原子上形成新化学键的合成方法将在很大程度上丰富化合物的结构多样性。在此，我们公开了异氰基与环状肟的银催化双官能化。该方法可以生成大量结构新颖且有趣的嘧啶二酮，并具有优异的原子经济性、良好的官能团兼容性和后期修饰的适应性。
• A new method for the preparation of Δ²-isoxazolin-5-ones from the oximes of ketones having an α-hydrogen atom
  作者：Jonathan S. Griffiths、Charles F. Beam、Charles R. Hauser

  DOI：10.1039/j39710000974

  日期：——

  Certain oximes having an α-hydrogen atom were treated with n-butyl-lithium (2 mol.equiv.) to give the 1,4-dianions, which were carbonated and acid-cyclized to give the Δ2-isoxazolin-5-ones.

  具有α-氢原子某些肟用正丁基锂处理（2摩尔当量），得到1,4-二价阴离子，将其碳酸和酸环化，得到的Δ 2 -isoxazolin -5-酮。