3-acetyl-2,3-dihydro-2,5-diphenyl-1,3,4-oxadiazole | 13864-76-1

• 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: 3-acetyl-2,3-dihydro-2,5-diphenyl-1,3,4-oxadiazole
• 英文别名: 1-(2,5-diphenyl-2H-1,3,4-oxadiazol-3-yl)ethanone
• CAS: 13864-76-1
• 化学式: C₁₆H₁₄N₂O₂
• 分子量: 266.299
• InChiKey: XOQIXXVBMACXEU-UHFFFAOYSA-N

物化性质

• 熔点：
  92-94 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• 沸点：
  387.8±45.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  41.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-acetyl-2,3-dihydro-2,5-diphenyl-1,3,4-oxadiazole 在 ammonium cerium(IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 0.42h， 以60%的产率得到2,5-二苯基-1,3,4-恶二唑
  参考文献：
  名称：

  环状N，O-和N，S-缩醛的合成，氧化和脱氢。第三部分 †往最‡转化N，O -acetals：3-酰基-1,3,4-恶二唑啉

  摘要：

  合成了各种醛和酮酰基hydr，并在酰化条件下将其环化成3-酰基-1,3,4-恶二唑啉。剖析了这些环化作用的范围和局限性以及可能的副反应（例如，形成开链的N，O-酰基肼基碳氢化合物）。首次提出了通过高锰酸钾或更简单地用硝酸铈铈（IV）铵（CAN）处理将3-酰基-1,3,4-恶二唑啉简单，方便，有效地脱氢为恶二唑的方法。2,2-二取代的3-酰基-1,3,4-恶二唑啉以及醛二酰基hydr的CAN氧化（2,5-二取代的3-酰基-1,3,4-恶二唑啉的开链异构体）再生母体羰基化合物。

  DOI：

  10.1002/jhet.5570440603
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 四氯化碳 、 乙酰氯 作用下， 生成 3-acetyl-2,3-dihydro-2,5-diphenyl-1,3,4-oxadiazole
  参考文献：
  名称：

  Stolle; Muench, Journal fur praktische Chemie (Leipzig 1954), 1904, vol. <2> 70, p. 412

  摘要：

  DOI：

文献信息

• 3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoles: A New Scaffold for the Selective Inhibition of Monoamine Oxidase B
  作者：Elias Maccioni、Stefano Alcaro、Roberto Cirilli、Sara Vigo、Maria Cristina Cardia、Maria Luisa Sanna、Rita Meleddu、Matilde Yanez、Giosuè Costa、Laura Casu、Peter Matyus、Simona Distinto

  DOI：10.1021/jm2002876

  日期：2011.9.22

  3-Acetyl-2,5-diaryl-2,3-dihydro-1,3,4-oxadiazoles were designed, synthesized, and tested as inhibitors against human monoamine oxidase (MAO) A and B isoforms. Several compounds, obtained as racemates, were identified as selective MAO-B inhibitors. The enantiomers of some derivatives were separated by enantioselective HPLC and tested. The R-enantiomers always showed the highest activity. Docking study

  设计，合成并测试了3-乙酰基-2,5-二芳基-2,3-二氢-1,3,4-恶二唑类化合物作为抗人单胺氧化酶（MAO）A和B同工型的抑制剂。鉴定为外消旋体的几种化合物被鉴定为选择性MAO-B抑制剂。通过对映选择性HPLC分离并测试了一些衍生物的对映异构体。在[R对映体总活性最高。对接研究和分子动力学模拟证明了推定的结合模式。我们得出的结论是，这些1,3,4-恶二唑衍生物是有前途的可逆和选择性MAO-B抑制剂。
• The mechanism of cyclization of 1,4-diaryl-1-azido-2,3-diazabuta-1,3-dienes to tetrazoles. Imidoyl azides stabilized by slow nitrogen inversion
  作者：Anthony F. Hegarty、Kieran Brady、Maria Mullane

  DOI：10.1039/p29800000535

  日期：——

  The imidoyl azides (9) are stabilized in the open chain azido form because of their configuration (which is Z about the CN bond) and slow ZE isomerisation. The rates of conversion of the azides (9) into the isomeric tetrazoles (12) have been measured and are characterized by a low sensitivity to solvent, a larger substituent effect for the remote substituent Y than for the adjacent X (ρY+ 1.45, ρX–0

  酰亚胺基叠氮化物（9）由于其构型（Z约为C N键）和缓慢的ZE异构化而稳定在开链叠氮基形式中。所述叠氮化物（9）的转化成异构体四唑（12）的比率进行了测量，并且特征在于低灵敏度到溶剂中，所述远程取代基的较大取代基期Y比在相邻X（ρ Ý + 1.45， ρ X -0.28在甲苯中在70℃），Δ小号‡ -6 CAL摩尔-1，K -1，和不敏感的催化剂。所有这些数据都指向氮转化，而不是决定速率的叠氮化物环化步骤本身。该Ë-叠氮化物未检测到，可能迅速环化为（12）。讨论了这些结果对其他开环叠氮化物的一般适用性。
• Sagitullin; Kost, Vestnik Moskovskogo Universiteta, 1959, vol. 14, # 4, p. 187,190
  作者：Sagitullin、Kost

  DOI：——

  日期：——
• Oxidation of azines with lead tetraacetate
  作者：Bernard T. Gillis、Maurice P. LaMontagne

  DOI：10.1021/jo01286a009

  日期：1967.11
• Antibacterial activity of chalcones, hydrazones and oxadiazoles against methicillin-resistant Staphylococcus aureus
  作者：Thaís Moreira Osório、Franco Delle Monache、Louise Domeneghini Chiaradia、Alessandra Mascarello、Taisa Regina Stumpf、Carlos Roberto Zanetti、Douglas Bardini Silveira、Célia Regina Monte Barardi、Elza de Fatima Albino Smânia、Aline Viancelli、Lucas Ariel Totaro Garcia、Rosendo Augusto Yunes、Ricardo José Nunes、Artur Smânia

  DOI：10.1016/j.bmcl.2011.11.059

  日期：2012.1

  The increase in antibiotic resistance due to multiple factors has encouraged the search for new compounds which are active against multidrug-resistant pathogens. In this context, chalcones, dihydrochalcones, hydrazones and oxadiazoles were tested against Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus (MRSA) isolates, which were obtained from clinical laboratories and were characterized as MRSA using traditional and molecular methods. Among 65 tested compounds, two chalcones, one dihydrochalcone and two hydrazones were active against MRSA. Based on the minimal inhibitory concentration and cytotoxicity, hydrazones provided a better selectivity index than chalcones. Active hydrazones are promising antibiotic-like substances and they should be the subject of further microbiological studies. (C) 2011 Elsevier Ltd. All rights reserved.