2-(3-phenyl-1,2,4-oxadiazol-5-yl) phenol | 79349-24-9

• 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-(3-phenyl-1,2,4-oxadiazol-5-yl) phenol
• 英文别名: 2-(3-Phenyl-1,2,4-oxadiazol-5-yl)phenol
• CAS: 79349-24-9
• 化学式: C₁₄H₁₀N₂O₂
• mdl: MFCD00814075
• 分子量: 238.246
• InChiKey: VNCIJMRFIRKERM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 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：
  59.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(3-phenyl-1,2,4-oxadiazol-5-yl) phenol 在 copper diacetate 、 potassium carbonate 、 一水合肼 、 维生素 C 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 24.0h， 生成 2-(4-((2-(3-phenyl-1,2,4-oxadiazol-5-yl)phenoxy) methyl)-1H-1,2,3-triazol-1-yl)acetohydrazide
  参考文献：
  名称：

  10.1039/d4ra02222j

  摘要：

  DOI：

  10.1039/d4ra02222j
• 作为产物：
  描述：

  N-苯甲酰基-2-羟基苯甲酰胺 在 盐酸羟胺 作用下， 以 吡啶 为溶剂， 反应 6.0h， 以55%的产率得到2-(3-phenyl-1,2,4-oxadiazol-5-yl) phenol
  参考文献：
  名称：

  Synthesis and study of the structure of o-hydroxyaryl-1,2,4-oxadiazoles

  摘要：

  DOI：

  10.1007/bf00767011

文献信息

• A metal-free tandem approach to prepare structurally diverse N-heterocycles: synthesis of 1,2,4-oxadiazoles and pyrimidinones
  作者：Puneet K. Gupta、Mohd. Kamil Hussain、Mohd. Asad、Ruchir Kant、Rohit Mahar、Sanjeev K. Shukla、Kanchan Hajela

  DOI：10.1039/c4nj00361f

  日期：——

  N-heterocycles, namely 1,2,4-oxadiazoles and 2,6 disubstituted pyrimidin-4-ones, have been synthesised in one pot via carboxamidation of amidines with aryl carboxylic acids and aryl propargylic acids under metal-free conditions.

  N-杂环化合物，即1,2,4-噁二唑和2,6-二取代嘧啶-4-酮，已经在无金属条件下通过酰胺与芳香羧酸和芳香丙炔酸的一锅法合成。
• Oxadiazoles, processes for their preparation and their use as medicaments
  申请人：Boehringer Ingelheim KG

  公开号：US06277872B1

  公开（公告）日：2001-08-21

  The invention relates to oxadiazole derivatives of general formula (I) wherein X, Y, Z and R1 are defined as described in the specification and claims, processes for preparing them and their use as pharmaceutical compositions.

  这项发明涉及一般式（I）的噁二唑衍生物，其中X、Y、Z和R1的定义如规范和索赔中所述，以及制备它们的过程以及它们作为药物组合物的用途。
• Excited-state acidity of bifunctional compounds Part 5 5-(2-Hydroxyphenyl)-3-phenyl-1,2,4-oxadiazole and 3-(2-hydroxyphenyl)-5-phenyl-1,2,4-oxadiazole
  作者：Carlos Carvalho、Ira Brinn、Wolfram Baumann、Heribert Reis、Zsolt Nagy

  DOI：10.1039/a702708g

  日期：——

  Fluorescence emission and excitation spectra and experimental dipole moments are presented for 5-(2-hydroxyphenyl)-3-phenyl-1,2,4-oxadiazole and 3-(2-hydroxyphenyl)-5-phenyl-1,2,4-oxadiazole. These data indicate that the long-wavelength emission of the former, in non-hydrogen bonding solvents, is due to a tautomeric PT structure. The latter exhibits only the ‘normal’ band. The striking difference in behavior between these two compounds of very similar structure is explained on the basis of coplanarity between the aryl ring in position 5 and the heterocycle ring, the aryl ring in the 3 position not being in the same plane.

  5-(2-羟苯基)-3-苯基-1,2,4-噁二唑和3-(2-羟苯基)-5-苯基-1,2,4-噁二唑的发射光谱和激发光谱以及实验偶极矩数据已呈现。这些数据显示，前者在非氢键溶剂中的长波长发射源于互变异构的PT结构。后者仅展示出“正常”的谱带。这两种结构高度相似的化合物在行为上的显著差异，可基于位于5位的芳环与杂环的共面性来解释，而位于3位的芳环并不处于同一平面。
• The role of the hydrogen bonding in cycloadditions of benzonitrile oxide with cyanophenols
  作者：Antonino Corsaro、Giuseppe Buemi、Ugo Chiacchio、Giancarlo Perrini、Venerando Pistarà、Roberto Romeo

  DOI：10.1016/0040-4020(96)00359-6

  日期：1996.6

  The reactivity of aromatic nitriles in cycloadditions with benzonitrile oxide is remarkably enhanced by the ortho-hydroxy substituent. Semiempirical PM3 calculations are in agreement with a hydrogen bonding effect.

  邻羟基取代基显着提高了环氧基加成反应中芳族腈与苯甲腈的反应性。半经验PM3的计算与氢键作用一致。
• Synthesis of Benzoxazines, Quinazolines and 4H-Benzo[e][1,3]thiazine by ANRORC Rearrangements of 1,2,4-Oxadiazoles
  作者：Alan Katritzky、Bogdan Draghici、Bahaa El-Gendy

  DOI：10.1055/s-0031-1289673

  日期：2012.2

  1,2,4-Oxadiazoles undergo ANRORC (addition of nucleophile, ring-opening and ring-closure) rearrangements upon reaction with excess of n-butyllithium to give benzoxazines, benzothiazines, and quinazolines in good yields under mild conditions. N,O-heterocycles - rearrangements - benzoxazines - quinazolines - benzothiazines

  1,2,4-恶二唑经历ANRORC（一个的ddition Ñ ucleophile，- [R ing- ö pening和- [R ing- Ç losure）重排在与过量的反应Ñ丁基锂，得到苯并恶嗪，苯并噻嗪，并且在在温和良好的收率的喹唑啉条件。 N，O杂环-重排-苯并恶嗪-喹唑啉-苯并噻嗪