4-硝基-3-苯基-1,2-恶唑 | 31301-41-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 4-硝基-3-苯基-1,2-恶唑
• 英文名称: 4-nitro-3-phenylisoxazole
• 英文别名: 3-Phenyl-4-nitro-isoxazol；4-Nitro-3-phenyl-1,2-oxazole
• CAS: 31301-41-4
• 化学式: C₉H₆N₂O₃
• 分子量: 190.158
• InChiKey: AMMAGHYZRLGORW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• 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-硝基-3-苯基-1,2-恶唑 在 苯甲醚 作用下， 以 氯仿 为溶剂， 反应 64.0h， 生成 (2SR,6SR)-6-nitro-4-phenyl-3-oxa-5-azatricyclo<5.2.2.0^2,6>undeca-4,8-diene
  参考文献：
  名称：

  4-硝基-2-苯基恶唑：恶唑系列中正常Diels-Alder反应的亲电子亲二烯体

  摘要：

  发现通过相应的硝基异恶唑1的热异构化获得的标题化合物2分别经历了与2，3-二甲基丁-1，3-二烯和环己-1，3-二烯的[2 + 4]环加成过程。

  DOI：

  10.1039/c39930000978
• 作为产物：
  描述：

  3-苯基异恶唑 在 硝酸 、 乙酸酐 作用下， 生成 4-硝基-3-苯基-1,2-恶唑
  参考文献：
  名称：

  Sokolov,S.D. et al., Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 2051 - 2055

  摘要：

  DOI：

文献信息

• [2+4] Cycloaddition reactions of 4-Nitro-3-phenylisoxazole with Carbo- and heterodienes
  作者：Stefania Turchi、Donatella Giomi、Rodolfo Nesi、Paola Paoli

  DOI：10.1016/0040-4020(95)00338-9

  日期：1995.6

  compound 4 reacted as a dienophile with open-chain and cyclic carbodienes as well as the 1-azadiene 16, to yield different polynuclear isoxazole systems. On the contrary, it gave rise preferentially to a Michael-type reaction with the dimethyluracil derivative 19 affording the cine-substitution product 23, whose structure was determined by an X-ray analysis. Some mechanistic features and synthetic opportunities

  标题化合物4作为亲二烯体与开链和环状碳二烯以及1-氮杂二烯16反应，产生不同的多核异恶唑体系。相反，其优先引起与二甲基尿嘧啶衍生物19的迈克尔型反应，从而提供电影取代产物23，其结构通过X射线分析确定。强调了一些机械特性和综合机会。
• A surprising new route to 4-nitro-3-phenylisoxazole
  作者：Henning Hopf、Aboul-fetouh E Mourad、Peter G Jones

  DOI：10.3762/bjoc.6.68

  日期：——

  A one-pot synthesis of 4-nitro-3-phenylisoxazole has been carried out by treatment of cinnamyl alcohol dissolved in acetic acid with sodium nitrite; in addition, 4-phenyl-3-furoxanmethanol was obtained in 40% yield.

  使用肉桂醇在乙酸中溶解后处理亚硝酸钠，进行了4-硝基-3-苯基异噁唑的一锅法合成；此外，以40%的收率得到了4-苯基-3-呋喃氧甲醇。
• Discovery of 4-nitro-3-phenylisoxazole derivatives as potent antibacterial agents derived from the studies of [3 + 2] cycloaddition
  作者：Yan Zhang、Zhiwu Long、Longjia Yan、Li Liu、Lan Yang、Yi Le

  DOI：10.1039/d2ra05009a

  日期：——

  Polysubstituted phenylisoxazoles were designed and synthesized to discover new antibacterial agents via [3 + 2] cycloaddition. Thirty-five compounds with a phenylisoxazole scaffold were characterized by NMR, HRMS, and X-ray techniques. After being evaluated against Xanthomonas oryzae (Xoo), Pseudomonas syringae (Psa), and Xanthomonas axonopodis (Xac), 4-nitro-3-phenylisoxazole derivatives were found

  设计并合成了多取代的苯基异恶唑，以通过[3 + 2] 环加成发现新的抗菌剂。通过 NMR、HRMS 和 X 射线技术对 35 种具有苯基异恶唑支架的化合物进行了表征。在针对米黄单胞菌( Xoo )、丁香假单胞菌( Psa ) 和轴突黄单胞菌( Xac )进行评估后，发现 4-硝基-3-苯基异恶唑衍生物具有更好的抗菌活性。进一步的研究表明，这些化合物的 EC 50值远优于阳性对照双汞噻唑。
• Asymmetric Synthesis of Bicyclic Isoxazolines via Dearomative Cycloaddition of 4-Nitroisoxazoles with Zwitterionic π-Allyl Palladium Species
  作者：Taiki Morita、Non Ito、Hiroyuki Nakamura

  DOI：10.1021/acs.orglett.3c01324

  日期：2023.7.7

  (S)-DTBM-SEGPHOS to give the corresponding bicyclic isoxazolines 3 and 4 in good to high yields with excellent enantioselectivities (≤99% ee). This synthetic approach could be applied to N-tosyl vinyl aziridine and 2-methylidenetrimethylene carbonate. Further transformations of the resulting cycloadducts 4a and 4i yielded not only its derivatives 10 and 11 but also the novel tetracyclic skeleton 12.

  在 Pd 2 (dba) 3和 ( S )-DTBM-SEGPHOS存在下，4-硝基异恶唑与乙烯基碳酸亚乙酯 ( 2 ) 发生对映选择性脱芳环加成反应，以良好到高产率和优异的对映选择性生成相应的双环异恶唑啉3和4 ( ≤99% ee）。该合成方法可应用于N-甲苯磺酰基乙烯基氮丙啶和2-亚甲基三亚甲基碳酸酯。所得环加合物4a和4i的进一步转化不仅产生了其衍生物10和11，还产生了新型四环骨架12。
• Process for production of vinyl chloride polymer
  申请人：Shin-Etsu Chemical Co., Ltd.

  公开号：EP0172427A2

  公开（公告）日：1986-02-26

  This process is a process for production of a vinyl chloride polymer by suspension polymerization or emulsion polymerization of vinyl chloride monomer or a mixture of vinyl chloride monomer with a vinyl monomer copolymerizable with said vinyl chloride monomer in an aqueous medium, characterized in that the polymerization is carried out in a polymerizer, the inner wall surface and portions of the auxiliary equipment thereof which may come into contact with the monomer during polymerization being previously coated with a scaling preventive comprising at least one selected from dyes, pigments and aromatic or heterocyclic compounds having at least 5 conjugated π bonds, while controlling the chloride ion concentration in the reaction mixture to not higher than 100 ppm. According to said process, scaling onto the inner wall surface of a polymerizer, etc. during polymerization can be prevented effectively and surely.

  该工艺是通过氯乙烯单体或氯乙烯单体与可与所述氯乙烯单体共聚的乙烯基单体混合物在水介质中进行悬浮聚合或乳液聚合来生产氯乙烯聚合物的工艺，其特征在于聚合是在聚合器中进行的、内壁表面及其辅助设备中可能在聚合过程中与单体接触的部分事先涂上一层防垢剂，该防垢剂至少包括一种选自染料、颜料和至少有 5 个共轭 π 键的芳香族或杂环化合物的防垢剂，同时控制反应混合物中的氯离子浓度不高于 100 ppm。根据上述工艺，可有效、可靠地防止聚合过程中聚合器等内壁表面结垢。