3-Methoxy-5-phenyl-1,2,4-oxadiazole | 3201-50-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Methoxy-5-phenyl-1,2,4-oxadiazole
• 英文别名: 3-methoxy-5-phenyl-[1,2,4]oxadiazole；3-Methoxy-5-phenyl-[1,2,4]oxadiazol；3-Methoxy-5-phenyl-1,2,4-oxadiazol
• CAS: 3201-50-1
• 化学式: C₉H₈N₂O₂
• 分子量: 176.175
• InChiKey: OWFPNQHKUMIYDG-UHFFFAOYSA-N

物化性质

• 熔点：
  57-59 °C
• 沸点：
  280.6±23.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  48.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-Methoxy-5-phenyl-1,2,4-oxadiazole 以 甲醇 为溶剂， 反应 2.0h， 生成 2-甲氧基-4(3H)-喹唑啉酮
  参考文献：
  名称：

  Buscemi, Silvestre; Cicero, Maria G.; Vivona, Nicolo, Journal of Heterocyclic Chemistry, 1988, vol. 25, p. 931 - 935

  摘要：

  DOI：
• 作为产物：
  描述：

  [[Amino(methoxy)methylidene]amino] benzoate 以80%的产率得到3-Methoxy-5-phenyl-1,2,4-oxadiazole
  参考文献：
  名称：

  Photoinduced Molecular Rearrangements. Some Investigations of the Photochemical Behavior of 3-(Acylamino)-1,2,5-Oxadiazoles (Furazans)

  摘要：

  Mechanistic investigations of the photochemical behavior of some 3-(acylamino)-1,2,5-oxadiazoles (furazans) are reported. Irradiations of 3-(aroylamino)-4-methyl- and 3-(acetylamino)-4-phenylfurazans at lambda = 254 nm in methanol, and in methanol containing pyrrolidine, are considered. Photochemical processes follow different routes depending on the actual chromophore in the photoreaction. In the irradiation of 3-(aroylamino)-4-methylfurazans, two photochemical pathways involving a different multiplicity of excited states are suggested: cleavage of the ring O(1)-N(5) bond via a singlet excited state (developing into nitrile oxides or carbodiimides, from which final products arise), or preliminary ring-closure involving the aroylamino group via a triplet excited state, respectively. In the irradiation of 3-(acetylamino)-4-phenylfurazan, photolytic intermediates arising from the cleavage of both the O(1)-N(2) and O(1)-N(5) bonds develop into the final products by reaction with the nucleophilic species present.

  DOI：

  10.1021/jo00118a028

文献信息

• [EN] SPIROPIPERIDINE ALLOSTERIC MODULATORS OF NICOTINIC ACETYLCHOLINE RECEPTORS<br/>[FR] MODULATEURS ALLOSTÉRIQUES DE SPIROPIPÉRIDINE DE RÉCEPTEURS NICOTINIQUES DE L'ACÉTYLCHOLINE
  申请人：MERCK SHARP & DOHME

  公开号：WO2020223136A1

  公开（公告）日：2020-11-05

  The present disclosure relates to compounds of formula (I) that are useful as modulators of 7α nAChR, compositions comprising such compounds, and the use of such compounds for preventing, treating, or ameliorating disease, particularly disorders of the central nervous system such as cognitive impairments in Alzheimer's disease, Parkinson's disease, and schizophrenia, as well as for L-DOPA induced-dyskinesia and inflammation.

  本公开涉及式(I)的化合物，这些化合物可用作7α nAChR的调节剂，包含这些化合物的组合物，以及利用这些化合物预防、治疗或改善疾病，特别是中枢神经系统疾病，如阿尔茨海默病、帕金森病和精神分裂症，以及L-多巴引起的运动障碍和炎症。
• Synthesis of Amino-1,2,4-triazoles by Reductive ANRORC Rearrangements of 1,2,4-Oxadiazoles
  作者：Antonio Palumbo Piccionello、Annalisa Guarcello、Silvestre Buscemi、Nicolò Vivona、Andrea Pace

  DOI：10.1021/jo102049r

  日期：2010.12.17

  reaction of various 1,2,4-oxadiazoles with an excess of hydrazine in DMF has been investigated. 3-Amino-1,2,4-triazoles are produced through a reductive ANRORC pathway consisting of the addition of hydrazine to the 1,2,4-oxadiazole followed by ring-opening, ring-closure, and final reduction of the 3-hydroxylamino-1,2,4-triazole intermediate. The general applicability of 1,2,4-oxadiazoles ANRORC reactivity

  已经研究了各种1,2,4-恶二唑与过量肼在DMF中的反应。3-氨基-1,2,4-三唑是通过还原性ANRORC途径生产的，该途径包括向1,1,2,4-恶二唑中添加肼，然后进行开环，闭环和最后还原3-的过程。羟氨基-1,2,4-三唑中间体 1,2,4-恶二唑类ANRORC反应性的一般适用性也在没有C（5）链接的吸电子基团的情况下得到证明。
• <i>N</i>-Halogen Compounds of Cyanamide Derivatives. VIII. A Convenient Method of Preparing 1,2,4-Oxadiazoles from<i>N</i>-Haloamidino Compounds
  作者：Toshio Fuchigami、Keijiro Odo

  DOI：10.1246/bcsj.49.3607

  日期：1976.12

  A new, efficient method for the preparation of 1,2,4-oxadiazoles from N-benzoylamidino compounds by treatment with t-butyl hypochlorite and sodium hydroxide has been devised. It was supposed that the ring formation proceeds via a nitrene intermediate.

  设计了一种新的、有效的方法，通过用次氯酸叔丁酯和氢氧化钠处理，从 N-苯甲酰脒基化合物制备 1,2,4-恶二唑。据推测，环的形成是通过氮烯中间体进行的。
• Synthesis of some disubstituted 1,2,4-oxadiazoles and furazans
  作者：B. W. Nash、R. A. Newberry、R. Pickles、W. K. Warburton

  DOI：10.1039/j39690002794

  日期：——

  No Beckmann rearrangement occurs when ω-chlorophenylglyoxime is treated with phosphorus pentachloride, and the steam-volatile product is 3-chloro-4-phenylfurazan (II; R = Cl), not, as previously reported, 3-chloro-5-phenyl-1,2,4-oxadiazole (I; R = Cl).

  当用五氯化磷处理ω-氯苯基乙二肟时，不会发生贝克曼重排，并且蒸汽挥发产物为3-氯-4-苯基呋喃山（II； R = Cl），而不是以前报道的3-氯-5-苯基- 1,2,4-恶二唑（I; R = Cl）。
• Ponzio; Avogadro, Gazzetta Chimica Italiana, 1927, vol. 57, p. 126
  作者：Ponzio、Avogadro

  DOI：——

  日期：——