2-methyl-5-(3-nitro-phenyl)-oxazole | 74048-11-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-methyl-5-(3-nitro-phenyl)-oxazole
• 英文别名: Oxazole, 2-methyl-5-(3-nitrophenyl)-；2-methyl-5-(3-nitrophenyl)-1,3-oxazole
• CAS: 74048-11-6
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: NKWSLJOPYDWQBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-diazo-1-(3-nitrophenyl)ethanone 、 乙腈 在 三氟化硼乙醚 作用下， 生成 2-methyl-5-(3-nitro-phenyl)-oxazole
  参考文献：
  名称：

  重氮化合物的酸催化分解。I. BF3催化重氮羰基化合物与腈类反应合成恶唑

  摘要：

  BF3 催化的腈中重氮羰基化合物的分解以高产率提供了相应的恶唑。该方法适用于间位和对位取代的重氮苯乙酮、重氮乙酸乙酯、1,2-二苯基-2-重氮乙酮、二苯甲酰重氮甲烷和重氮丙二酸二甲酯等重氮羰基化合物。双（重氮酮）如末端双（重氮乙酰化）烷烃（III1-4：n=6, 8, 10, 12）和间和对双（重氮乙酰基）苯也在类似的反应中得到相应的双恶唑。该反应被解释为通过甜菜碱中间体的逐步机制，由 BF3 对重氮羰基化合物的羰基氧的攻击引发。描述了恶唑的发射光谱。

  DOI：

  10.1246/bcsj.52.3597

文献信息

• Substituted heterocyclyl phenylformamidines, processes for their preparation and their pharmaceutical use
  申请人：ISTITUTO DE ANGELI S.p.A.

  公开号：EP0094727A2

  公开（公告）日：1983-11-23

  Object of the present invention are new pharmacologically active substituted heterocyclylphenylformamidines of formula in which A represents a hydrogen atom, an amino group which may be substituted by one or two alkyl groups having 1 to 3 carbon atoms or a saturated heterocyclic ring, R represents a hydrogen atom or a methyl group, R1 represents a linear or branched alkyl group which may contain 1 or 2 heteroatoms such as a sulfur, an oxygen or nitrogen atom or may form a substituted or an unsubstituted cyclic ring, an alkenyl group, an alkynyl group, a cycloalkyl group or a phenyl group, R2 and R3 which may be the same or different, represent a hydrogen atom, an alkyl or alkoxy group having 1 to 3 carbon atom or a halogen atom, m and n represent 0 or 1, Het represents a substituted or unsubstituted heterocyclic ring containing from 1 to 3 heteroatoms (except the imidazole ring when R1 is a linear or branched alkyl group not containing heteroatoms and R2 and R3 are both hydrogen atoms), tautomers thereof and acid addition salts of the aforesaid compounds. Processes for preparation of the compounds of formula (I) and their intermediates as well as pharmaceutical compositions containing them are also object of this invention. The new compounds are H2-receptor blocking agents, inhibit gastric acid secretion, and are useful antiulcer agents.

  本发明的目的是具有药理活性的新的取代杂环苯基甲脒，其式为 其中 A 代表氢原子、可被一个或两个具有 1 至 3 个碳原子的烷基或饱和杂环取代的氨基，R 代表氢原子或甲基，R1 代表直链或支链烷基，该烷基可含有 1 或 2 个杂原子，如硫原子、氧原子或氮原子，或可形成取代或未取代的环环、烯基、炔基、环烷基或苯基、R2和R3可以相同或不同，代表氢原子、具有1至3个碳原子的烷基或烷氧基或卤素原子，m和n代表0或1，Het代表含有1至3个杂原子的取代或未取代的杂环（当R1为不含杂原子的直链或支链烷基且R2和R3均为氢原子时，咪唑环除外）、其同系物以及上述化合物的酸加成盐。制备式（I）化合物及其中间体以及含有它们的药物组合物的工艺也是本发明的目的。 新化合物是 H2 受体阻断剂，可抑制胃酸分泌，是有效的抗溃疡剂。
• The Acid Catalyzed Decomposition of Diazo Compounds. I. Synthesis of Oxazoles in the BF₃Catalyzed Reaction of Diazo Carbonyl Compounds with Nitriles
  作者：Toshikazu Ibata、Ryohei Sato

  DOI：10.1246/bcsj.52.3597

  日期：1979.12

  The BF3-catalyzed decomposition of diazo carbonyl compounds in nitriles have afforded the corresponding oxazoles in high yields. This method is applicable to diazo carbonyl compounds such as m- and p-substituted diazoacetophenones, ethyl diazoacetate, 1,2-diphenyl-2-diazoethanone, dibenzoyldiazomethane, and dimethyl diazomalonate. Bis(diazo ketone)s such as terminal bis(diazoacetylated) alkanes (III1−4:

  BF3 催化的腈中重氮羰基化合物的分解以高产率提供了相应的恶唑。该方法适用于间位和对位取代的重氮苯乙酮、重氮乙酸乙酯、1,2-二苯基-2-重氮乙酮、二苯甲酰重氮甲烷和重氮丙二酸二甲酯等重氮羰基化合物。双（重氮酮）如末端双（重氮乙酰化）烷烃（III1-4：n=6, 8, 10, 12）和间和对双（重氮乙酰基）苯也在类似的反应中得到相应的双恶唑。该反应被解释为通过甜菜碱中间体的逐步机制，由 BF3 对重氮羰基化合物的羰基氧的攻击引发。描述了恶唑的发射光谱。