4-(4-硝基苯基)-2-苯基噁唑 | 10004-42-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-(4-硝基苯基)-2-苯基噁唑
• 英文名称: 4-(4-nitrophenyl)-2-phenyloxazole
• 英文别名: 4-(4-nitrophenyl)-2-phenyl-1,3-oxazole
• CAS: 10004-42-9
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: OAPKOHYAIHCLSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(4-硝基苯基)-2-苯基噁唑 在 吡啶 、 溶剂黄146 、 锌 作用下， 以 二氯甲烷 为溶剂， 生成 2-chloro-N-(4-(2-phenyloxazol-4-yl)phenyl)benzamide
  参考文献：
  名称：

  Discovery of amide replacements that improve activity and metabolic stability of a bis-amide smoothened antagonist hit

  摘要：

  A bis-amide antagonist of Smoothened, a seven-transmembrane receptor in the Hedgehog signaling pathway, was discovered via high throughput screening. In vitro and in vivo experiments demonstrated that the bis-amide was susceptible to N-acyl transferase mediated amide scission. Several bioisosteric replacements of the labile amide that maintained in vitro potency were identified and shown to be metabolically stable in vitro and in vivo. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.07.052
• 作为产物：
  描述：

  苯甲酸 在 叠氮基三甲基硅烷 作用下， 以 甲苯 为溶剂， 反应 48.0h， 生成 4-(4-硝基苯基)-2-苯基噁唑
  参考文献：
  名称：

  A novel synthetic method of 2,4-disubstituted oxazoles using carboxylic acid-derived Bu2Sn[OC(O)R]2

  摘要：

  A novel synthetic method for the preparation of 2,4-disubstituted oxazoles was developed, entailing the reaction of dibutyltin diacylates Bu2Sn[OC(O)R](2) with 1-substituted acetylenes and TMSN3 to afford a range of 2,4-disubstituted oxazoles in good yields. (C) 2020 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2020.151983

文献信息

• Radical C–H Arylation of Oxazoles with Aryl Iodides: dppf as an Electron-Transfer Mediator for Cs₂CO₃
  作者：Zhengwei Guo、Man Li、Xue-Qing Mou、Gang He、Xiao-Song Xue、Gong Chen

  DOI：10.1021/acs.orglett.8b00530

  日期：2018.3.16

  A radical C–H arylation reaction of oxazoles with (hetero)aryl iodides using Cs2CO3 as base/electron donor and 1,1′-bis(diphenylphosphino) ferrocene (dppf) as a catalytic SET mediator is reported. The overall reaction likely follows the general base-promoted homolytic aromatic substitution mechanism through a radical-chain pathway. DFT calculations suggest that dppf forms a complex with CsCO3–, enhancing

  报道了使用Cs 2 CO 3作为碱/电子给体和1,1'-双（二苯基膦基）二茂铁（dppf）作为催化SET介体，恶唑与（杂）芳基碘化物的自由基CH芳基化反应。整个反应可能通过自由基链途径遵循一般的碱促进的均质芳族取代机理。DFT计算表明，dppf与CsCO 3 –形成络合物，增强了SET还原能力，可从ArI生成芳基。
• Photochemical Transformation of <i>O</i> -(β-Arylethyl) Arylimidates into 2,4-Diaryl-5-iodoxazoles with 1,3-Diiodo-5,5-dimethylhydantoin
  作者：Aya Saito、Hideo Togo

  DOI：10.1002/ejoc.202000383

  日期：2020.6.16

  2,4‐Diaryl‐5‐iodoxazoles could be obtained by the treatment of O ‐(β‐arylethyl) arylimidates with 1,3‐diiodo‐5,5‐dimethylhydantoin (DIH) under irradiation with a tungsten lamp. This reaction proceeds through multiple stets, i.e., formation of N ‐iodoimidate, iminyl radical, 1,5‐H shift, 5‐exo‐tet cyclization to oxazoline, oxidation to oxazole, and iodination to 5‐iodoxazole.

  在钨丝灯下用1,3-二碘-5,5-二甲基乙内酰脲（DIH）处理O-（β-芳基乙基）芳基亚氨酸酯可以得到2,4-二芳基-5-碘恶唑。该反应通过多个步骤进行，即形成N-碘亚氨酸盐，亚氨基，1,5-H转移，5- exet -tet环化为恶唑啉，氧化为恶唑和碘化为5-碘恶唑。
• Studies on Cerebral Protective Agents. VII. Synthesis of Novel 4-Arylazole Derivatives with Anti-anoxic Activity.
  作者：Mitsuru OHKUBO、Atsushi KUNO、Hiroyoshi SAKAI、Hisashi TAKASUGI

  DOI：10.1248/cpb.43.947

  日期：——

  Novel 4-arylazole (i.e. thiazole, oxazole, and imidazole) derivatives, possessing an amino moiety at the C-5 position of the azole ring, were prepared and tested for anti-anoxic (AA) activity in mice. Among them, 5-(4-methylpiperazin-1-yl)methyl-4-(3-nitrophenyl)-2-phenylthiazole (3b, FR75094) possessed significant AA activity (10 mg/kg, i.p. and 100 mg/kg, p.o., respectively), and was also effective on anti-lipid peroxidation (ALP) assay and inhibited arachidonate-induced cerebral edema in rats. Structure-activity relationships in regard to AA activity of this series of compounds are discussed.

  新型4元氮杂环（即噻唑、噁唑和咪唑）衍生物，其氮杂环第5位具有氨基基团，被制备并用于测试对小鼠的抗缺氧（AA）活性。其中，5-（4-甲基哌嗪-1-基）甲基-4-（3-硝基苯基）-2-苯基噻唑（3b，FR75094）显示出显著的AA活性（分别为10 mg/kg腹腔注射和100 mg/kg口服），并且在抗脂质过氧化（ALP）测试中有效，抑制了花生四烯酸引起的大鼠脑水肿。讨论了这一系列化合物在AA活性方面的构效关系。
• Hypervalent Iodine(III) Sulfonate Reagent Mediated Synthesis of 4-Aryl-2-Phenyloxazoles in Ionic Liquid
  作者：Hui-Ting Cheng、Rei-Sheu Hou、Huey-Min Wang、Ling-Ching Chen

  DOI：10.1002/jccs.200800136

  日期：2008.8

  A new and efficient method for the synthesis of 4-aryl-2-phenyloxazoles is described which is based upon the reaction of α-[(2,4-dinitrobenzene)sulfonyl]oxy ketone intermediates with benzamide in ionic liquid.

  介绍了一种基于α-[(2,4-二硝基苯)磺酰基]氧基酮中间体与苯甲酰胺在离子液体中反应合成4-芳基-2-苯基恶唑的新方法。
• OXAZOLE COMPOUNDS COMPOSITIONS AND METHODS OF USE
  申请人：Brown Matthew

  公开号：US20110060011A1

  公开（公告）日：2011-03-10

  The present invention relates generally to compounds represented in Formula (I), pharmaceutical compositions comprising them and methods of treating of diseases or disorders such as cancer.

  本发明涉及一般表示为公式(I)的化合物，包括它们的制药组合物和用于治疗癌症等疾病或障碍的方法。