2-(4-氟苯基)-5-苯基-1,3,4-恶二唑 | 1580-50-3

• 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-(4-氟苯基)-5-苯基-1,3,4-恶二唑
• 英文名称: 2-(4-fluorophenyl)-5-phenyl-1,3,4-oxadiazole
• 英文别名: 2-Phenyl-5-<4-fluor-phenyl>-1,3,4-oxadiazol
• CAS: 1580-50-3
• 化学式: C₁₄H₉FN₂O
• 分子量: 240.237
• InChiKey: QHKMUJVIGDJRLU-UHFFFAOYSA-N

物化性质

• 熔点：
  147 °C
• 沸点：
  374.2±44.0 °C(Predicted)
• 密度：
  1.241±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  38.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-氟苯基)-5-苯基-1,3,4-恶二唑 、 咔唑 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以55%的产率得到2-(4-(9H-carbazol-9-yl)phenyl)-5-phenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Bipolar Molecules with High Triplet Energies: Synthesis, Photophysical, and Structural Properties

  摘要：

  This article sheds new light on the interplay of electronic and conformational effects in luminescent bipolar molecules. A series of carbazole/1,3,4-oxadiazole hybrid molecules is described in which the optoelectronic properties are systematically varied by substituent effects which tune the intramolecular torsion angles. The synthesis, photophysical properties, cyclic voltammetric data, X-ray crystal structures, and DFT calculations are presented. Excited state intramolecular charge transfer (ICT) is observed from the donor carbazole/2,7-dimethoxycarbazole to the acceptor phenyl/diphenyloxadiazole moieties. Introducing more bulky substituents onto the diphenyloxadiazole fragment systematically increases the singlet and triplet energy levels (E-S and E-T) and blue shifts the absorption and emission bands. The triplet excited state is located mostly on the oxadiazole unit. The introduction of 2,7-dimethoxy substituents onto the carbazole moiety lowers the value of E-S, although E-T is unaffected, which means that the singlet triplet gap is reduced (for 7b E-S - E-T = 0.61 eV). A strategy has been established for achieving unusually high triplet levels for bipolar molecules (E-T = 2.64-2.78 eV at 14 K) while at the same time limiting the increase in the singlet energy.

  DOI：

  10.1021/jo201488v
• 作为产物：
  描述：

  Benzaldehyd-4-fluorbenzoylhydrazon 在 Co(dmgH)(dmgH₂)Cl₂ 、 10-甲基-9-均三甲苯基吖啶高氯酸盐 作用下， 以 乙腈 为溶剂， 以95 %的产率得到2-(4-氟苯基)-5-苯基-1,3,4-恶二唑
  参考文献：
  名称：

  无氧化剂条件下光氧化还原/钴催化级联氧化合成 2,5-二取代 1,3,4-恶二唑

  摘要：

  通过使用有机吖啶光催化剂和钴肟催化剂，开发了一种有效的无氧化剂、光氧化还原介导的级联环化策略，用于合成 1,3,4-恶二唑。各种酰腙已转化为相应的1,3,4-恶二唑产品，收率高达96%，H 2是唯一的副产物。机理实验和密度泛函理论 (DFT) 计算研究表明，光激发 Mes–Acr + *氧化以及去质子化产生的 π 自由基是以碳为中心的自由基，而不是以氧为中心的自由基，这是造成这种转变的原因。该方法的实用性突出是直接从市售醛和酰肼开始的一锅克级合成。

  DOI：

  10.1021/acs.joc.3c01078

文献信息

• TiCl₄ mediated facile synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
  作者：Lin Zhang、Yu Yu、Qiang Tang、Jianyong Yuan、Dongzhi Ran、Binghua Tian、Tao Pan、Zongjie Gan

  DOI：10.1080/00397911.2019.1700521

  日期：2020.2.1

  Abstract An efficient method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles has been developed. Various hydrazides or thionyl hydrazides readily react with DMA derivatives in the presence of TiCl4 as a catalyst to afford the desired products. This protocol provides a simple and economical procedure that affords the target products with good yields and wide substrate

  摘要 开发了一种合成2,5-二取代1,3,4-恶二唑和1,3,4-噻二唑的有效方法。在作为催化剂的 TiCl4 存在下，各种酰肼或亚硫酰酰肼很容易与 DMA 衍生物反应，得到所需的产物。该协议提供了一种简单且经济的程序，可提供具有良好产量和广泛底物范围的目标产品。图形概要
• Greener and rapid access to bio-active heterocycles: one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles
  作者：Vivek Polshettiwar、Rajender S. Varma

  DOI：10.1016/j.tetlet.2007.11.165

  日期：2008.1

  A novel one-pot solvent-free synthesis of 1,3,4-oxadiazoles and 1,3,4-thiadiazoles by condensation of acid hydrazide and triethyl orthoalkanates under microwave irradiations is reported. This green protocol was catalyzed efficiently by solid supported Nafion®NR50 and phosphorus pentasulfide in alumina (P4S10/Al2O3) with excellent yields.

  报道了在微波辐射下通过酰肼与原烷基三乙基酯的缩合反应得到的一种新颖的无锅无溶剂合成1,3,4-恶二唑和1,3,4-噻二唑的方法。此绿色协议是有效地由固体负载的Nafion催化® NR50和五硫化二磷在氧化铝（P 4小号10 /的Al 2 ö 3具有优良的产率）。
• Oxidative Cyclization of Aromatic Aldehyde<i>N</i>‐Acylhydrazones by bis(Trifluoroacetoxy)iodobenzene
  作者：Zhenhua Shang

  DOI：10.1080/00397910600773650

  日期：2006.10

  Abstract Aromatic aldehyde N‐acylhydrazones were oxidized into 2,5‐disubstituted 1,3,4‐oxadiazoles with bis(trifluoroacetoxy)iodobenzene in CHCl3 or DMSO at room temperature in good to excellent yields.

  摘要 芳香醛 N-酰基腙在室温下用双（三氟乙酰氧基）碘苯在 CHCl3 或 DMSO 中氧化成 2,5-二取代的 1,3,4-恶二唑，产率良好至极好。
• ¹⁷ O NMR studies of substituted 1,3,4-oxadiazoles
  作者：Błażej Gierczyk、Maciej Zalas、Marcin Kaźmierczak、Jakub Grajewski、Radosław Pankiewicz、Bożena Wyrzykiewicz

  DOI：10.1002/mrc.2804

  日期：2011.10

  Three series of substituted 1,3,4-oxadiazoles were studied by (17)O NMR spectroscopy. Chemical shifts values were correlated with empirical Hammett parameters as well as calculated bond lengths and chemical shielding values.

  通过（17）O NMR光谱研究了三个系列的取代的1,3,4-恶二唑。化学位移值与经验的哈米特参数以及计算的键长和化学屏蔽值相关。
• 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。