(E)-2-phenyl-5-styryl-1,3,4-oxadiazole | 1874-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-2-phenyl-5-styryl-1,3,4-oxadiazole
• 英文别名: 2-phenyl-5-[(E)-2-phenylvinyl]-1,3,4-oxadiazole；2-phenyl-5-[(E)-2-phenylethenyl]-1,3,4-oxadiazole
• CAS: 1874-31-3
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: MIQDFIINRMWWAK-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  19
• 可旋转键数：
  3
• 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：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-phenyl-5-styryl-1,3,4-oxadiazole 、 氨基邻苯二甲胺 在 lead(IV) acetate 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以44%的产率得到2-phenyl-5-[(E)-3-phenyl-1-phthalimidoaziridin-2-yl]-1,3,4-oxadiazole
  参考文献：
  名称：

  Oxidative addition of N-aminophthalimide to 2-alkenyl-1,3,4-oxadiazoles. Synthesis of aziridinyloxadiazoles

  摘要：

  Oxidation of N-aminophthalimide with lead tetraacetate in the presence of 2-[(E)-2-arylethenyl]-5-phenyl-1,3,4-oxadiazoles gives the corresponding 2-(3-aryl-1-phthalimidoaziridin-2-yl)-5-phenyl-1,3,4-oxadiazoles. From 2-phenyl-5-[(1E,3E)-4-phenylbuta-1,3-dien-1-yl]-1,3,4-oxadiazole only the addition product at both C=C bonds was obtained, while in the reaction with 2,5-bis[(E)-2-phenylethenyl]-1,3,4-oxadiazole both mono- and bis-adducts were isolated.

  DOI：

  10.1134/s1070428007070172
• 作为产物：
  描述：

  2,2-dibromostyrene 在 copper(l) iodide 、 palladium diacetate 、 三乙胺 、 亚磷酸二乙酯 、 lithium tert-butoxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 生成 (E)-2-phenyl-5-styryl-1,3,4-oxadiazole
  参考文献：
  名称：

  Microwave-Assisted Pd/Cu-Catalyzed C-8 Direct Alkenylation of Purines and Related Azoles: An Alternative Access to 6,8,9-Trisubstituted Purines

  摘要：

  An efficient microwave-assisted palladium/copper comediated C-8 direct alkenylation of purines with styryl bromides has been developed. The method is regioselective, functional group tolerant, rapid, and compatible with other related azoles. Combined with subsequent nucleophilic substitution, it provides an easy access to new 6,8,9-trisubstituted purines.

  DOI：

  10.1021/jo201893h

文献信息

• Design, synthesis, modelling studies and biological evaluation of 1,3,4-oxadiazole derivatives as potent anticancer agents targeting thymidine phosphorylase enzyme
  作者：Shalini Bajaj、Maushmi S. Kumar、Hussain Tinwala、Mayur YC

  DOI：10.1016/j.bioorg.2021.104873

  日期：2021.6

  identified no signs of clinical toxicity was observed. The SARs study of synthesized derivatives revealed that the substitution of phenyl ring with electron withdrawing group at ortho position showed significant TP inhibitory activity compared to para substitution. The experimental data suggests that 1,3,4-oxadiazole with substituted phenyl can be taken as a lead for the design of efficient TP inhibitors

  设计并合成了一系列具有取代苯环的新型 1,3,4-恶二唑衍生物，目的是发现靶向胸苷磷酸化酶 (TP) 的新型抗癌药物。1,3,4-恶二唑衍生物在实验室中通过简单方便的方法合成。所有合成化合物的化学结构均通过 IR、1 H NMR 和质谱方法表征，并通过 MTT 方法评估对两种乳腺癌细胞系（MCF-7 和 MDA-MB-231）的细胞毒性。此外，TP 测定的结果确定 1,3,4-恶二唑分子部分通过抑制胸苷磷酸化显示出抗癌活性。TP 测定鉴定了SB8和SB9作为对两种细胞系都具有抗癌活性的潜在抑制剂。分子对接研究确认了分子在 TP 活性位点氨基酸残基处的取向和结合相互作用（PDB：1UOU）。化合物SB8在 5000 mg/kg 剂量下的急性毒性研究已确定未观察到临床毒性迹象。合成衍生物的非典研究表明，与在电子吸引性基团的苯基环的取代邻相比位置表明显著TP抑制活性对代换。实验数据表明，具有取代苯基的1
• A mild and efficient one pot synthesis of 1,3,4-oxadiazoles from carboxylic acids and acyl hydrazides
  作者：Hemaka A. Rajapakse、Hong Zhu、Mary Beth Young、Bryan T. Mott

  DOI：10.1016/j.tetlet.2006.05.051

  日期：2006.7

  A convenient one pot method for the synthesis of 2,5-disubstituted 1,3,4-oxadiazoles from acids and acyl hydrazides is reported. Acid activation with CDI, followed by coupling with the desired acylhydrazide and dehydration in the same pot with Ph3P and CBr4 affords the corresponding 1,3,4-oxadiazoles in good yield. The scope of the acid and acylhydrazide components is presented.

  据报道，一种方便的一锅法从酸和酰基酰肼合成2，5-二取代的1,3,4-恶二唑。用CDI进行酸活化，然后与所需的酰肼偶联，并在同一罐中用Ph 3 P和CBr 4脱水，得到相应的1,3,4-恶二唑，收率很高。给出了酸和酰肼组分的范围。
• 1,3,4-Oxadiazole formation as traceless release in solid phase organic synthesis
  作者：Sara Cesarini、Nicoletta Colombo、Maurizio Pulici、Eduard R. Felder、Wolfgang K.-D. Brill

  DOI：10.1016/j.tet.2006.08.016

  日期：2006.10

  Oxadiazoles were generated upon a dehydrative cyclization reaction with 2-acyl hydrazides bound to the polymeric support via one of their N atoms using TFAA as a dehydration agent.

  使用TFAA作为脱水剂，通过与2-酰基酰肼通过其N原子之一结合到聚合物载体上的脱水环化反应，生成恶二唑。
• An Improved Synthesis of 2-Aryl- and 2-Alkenyl-1,3,4-oxadiazoles by Using Copper(II) Oxide Nanoparticles as a Catalyst
  作者：Biswanath Das、N. Salva Reddy、P. Raghavendar Reddy

  DOI：10.1055/s-0034-1380923

  日期：——

  Abstract 2-Aryl- and 2-alkenyl-1,3,4-oxadiazoles were efficiently synthesized in high yields by treatment of 1,3,4-oxadiazoles with aryl or alkenyl halides, respectively, in the presence of copper(II) oxide nanoparticles as a catalyst. The reusability of the catalyst is an important advantage in relation to practical applications of this synthesis. 2-Aryl- and 2-alkenyl-1,3,4-oxadiazoles were efficiently

  摘要 通过在氧化铜（II）纳米粒子的存在下分别用芳基或烯基卤化物处理1,3,4-恶二唑，可以高收率高效合成2-芳基和2-烯基-1,3,4-恶二唑作为催化剂。相对于该合成的实际应用，催化剂的可重复使用性是重要的优点。 通过在氧化铜（II）纳米粒子的存在下分别用芳基或烯基卤化物处理1,3,4-恶二唑，可以高收率高效合成2-芳基和2-烯基-1,3,4-恶二唑作为催化剂。相对于该合成的实际应用，催化剂的可重复使用性是重要的优点。
• Oxidative cyclization of N-aroylhydrazones to 2-(2-arylethenyl)-1,3,4-oxadiazoles using DDQ as an efficient oxidant
  作者：Karolina Jasiak、Agnieszka Kudelko

  DOI：10.1016/j.tetlet.2015.09.018

  日期：2015.10

  A series of novel 5-aryl-2-(2-arylethenyl)-1,3,4-oxadiazoles were synthesized by the 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) promoted oxidative cyclization of N′-(arylmethylidene)-3-arylacrylohydrazides. A facile and efficient one-pot protocol using the starting 3-arylacrylohydrazides and aromatic aldehydes is also reported. Short reaction times, high yields, a simple work-up procedure and the possibility

  通过2,3-二氯-5,6-二氰基苯并醌（DDQ）促进N '-（芳基亚甲基）的氧化环化反应合成了一系列新型的5-芳基-2-（2-芳基乙烯基）-1,3,4-恶二唑）-3-芳基丙烯酰肼。还报道了一种使用起始的3-芳基丙烯酰肼和芳族醛的简便有效的一锅操作方案。反应时间短，产率高，简单的后处理步骤以及氧化剂再生的可能性使所报道的方法成为合成2,5-二芳基-1,3,4-恶二唑的有前途的替代方法。