2-(3-甲基苯基)-5-苯基-1,3,4-恶二唑 | 1874-39-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(3-甲基苯基)-5-苯基-1,3,4-恶二唑
• 英文名称: 2-phenyl-5-(m-tolyl)-1,3,4-oxadiazole
• 英文别名: 2-(3-methylphenyl)-5-phenyl-1,3,4-oxadiazole；2-(m-tolyl)-5-phenyl-1,3,4-oxadiazole；2-(Phenyl)-5-(m-tolyl)-1,3,4-oxadiazol；2-Phenyl-5-m-tolyl-[1,3,4]oxadiazole
• CAS: 1874-39-1
• 化学式: C₁₅H₁₂N₂O
• mdl: MFCD00085484
• 分子量: 236.273
• InChiKey: CTNBTTIMTWNDOW-UHFFFAOYSA-N

物化性质

• 熔点：
  107-109 °C
• 沸点：
  400.1±38.0 °C(Predicted)
• 密度：
  1.149±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  38.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N'-benzoyl-3′-methylbenzohydrazide 在 三氯氧磷 作用下， 生成 2-(3-甲基苯基)-5-苯基-1,3,4-恶二唑
  参考文献：
  名称：

  Grekow,A.P.; Schvaika,O.P., Journal of general chemistry of the USSR, 1960, vol. 30, p. 3763 - 3766

  摘要：

  DOI：

文献信息

• Electrochemical Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles from α-Keto Acids and Acylhydrazines Under Mild Conditions
  作者：Fangling Lu、Fengping Gong、Liangsen Li、Kan Zhang、Zhen Li、Xinwei Zhang、Ying Yin、Ying Wang、Ziwei Gao、Heng Zhang、Aiwen Lei

  DOI：10.1002/ejoc.202000311

  日期：2020.6.16

  An efficient and environmentally benign electrosynthesis of 2,5‐disubstituted 1,3,4‐oxadiazoles from α‐keto acids and acylhydrazines under metal‐free and external oxidant free conditions has been developed. A broad range of acylhydrazines and α‐keto acids were compatible, and the reaction could be conducted in gram scale with high reaction efficiency.

  在无金属和无外部氧化剂的条件下，已经开发了由α-酮酸和酰基肼高效合成2,5-二取代的1,3,4-恶二唑的方法。广泛的酰基肼和α-酮酸是相容的，该反应可以以克级进行，反应效率高。
• Palladium-catalyzed one-pot synthesis of diazoles via tert-butyl isocyanide insertion
  作者：Xiang-Yuan Fan、Xiao Jiang、Ying Zhang、Zhen-Bang Chen、Yong-Ming Zhu

  DOI：10.1039/c5ob01328c

  日期：——

  An efficient one-pot palladium-catalyzed reaction for the synthesis of diazoles from readily available hydrazides and aryl halide via isocyanide insertion/cyclization sequence has been developed.

  已经开发出一种高效的钯催化的单锅反应，用于从易于获得的肼酯和芳基卤化物通过异氰插入/环化序列合成哒唑。

• C–H arylation of azaheterocycles: a direct ligand-free and Cu-catalyzed approach using diaryliodonium salts
  作者：Dalip Kumar、Meenakshi Pilania、V. Arun、Savita Pooniya

  DOI：10.1039/c4ob01061b

  日期：——

  An efficient and high yielding Cu-catalyzed direct C–H arylation of azaheterocycles including oxadiazoles, thiadiazoles, benzoxazoles and benzothiazoles has been achieved by employing easily accessible diaryliodonium salts.

  通过使用易于获得的二芳基碘盐，成功实现了一种高效且高产率的铜催化的直接C-H键芳基化反应，其中包括嘧啶、噻二唑、苯并噁唑和苯并噻唑等氮杂环化合物的合成。
• Photoinduced Copper-Catalyzed C−H Arylation at Room Temperature
  作者：Fanzhi Yang、Julian Koeller、Lutz Ackermann

  DOI：10.1002/anie.201512027

  日期：2016.4.4

  Room‐temperature azole C−H arylations were accomplished with inexpensive copper(I) compounds by means of photoinduced catalysis. The expedient copper catalysis set the stage for site‐selective C−H arylations of non‐aromatic oxazolines under mild reaction conditions, and provides step‐economical access to the alkaloid natural products balsoxin and texamine.

  通过廉价的铜（I）化合物通过光诱导催化可实现室温的吡咯CH H芳基化反应。适宜的铜催化为温和的反应条件下非芳香族恶唑啉的位点选择性CH芳基化奠定了基础，并为生物碱天然产物balsoxin和texamine提供了经济实惠的步骤。
• One-pot cyclization/decarboxylation of α-keto acids and acylhydrazines for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles under transition-metal-free conditions
  作者：Peng Gao、Juan Wang、Zijing Bai、Hualei Cheng、Jian Xiao、Mengnan Lai、Desuo Yang、Mingjin Fan

  DOI：10.1016/j.tetlet.2016.09.007

  日期：2016.10

  A one-pot KI/TBHP-mediated oxidative cyclization of α-keto acids with acylhydrazines was developed. A series of functional 2,5-disubstituted 1,3,4-oxadiazoles were synthesized through a tandem keto amine condensation followed by oxidative cyclization and decarboxylation reactions. This procedure was achieved under transition-metal-free conditions and showed advantages including readily available materials

  开发了单罐KI / TBHP介导的α-酮酸与酰肼的氧化环化反应。通过串联酮胺缩合，然后进行氧化环化和脱羧反应，合成了一系列功能性的2,5-二取代的1,3,4-恶二唑。该方法是在无过渡金属的条件下完成的，并显示出以下优点：容易获得的材料，温和的反应条件和良好的基团耐受性。