3,5-bis(4-hydroxyphenyl)-1,2,4-oxadiazole | 364595-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3,5-bis(4-hydroxyphenyl)-1,2,4-oxadiazole
• 英文别名: 3,5-di(4-oxyphenyl)-1,2,4-oxadiazole；4,4'-(1,2,4-Oxadiazole-3,5-diyl)diphenol；4-[5-(4-hydroxyphenyl)-1,2,4-oxadiazol-3-yl]phenol
• CAS: 364595-09-5
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: JDSJZQNILAOWDQ-UHFFFAOYSA-N

物化性质

• 沸点：
  501.2±60.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 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：
  79.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,5-bis(4-hydroxyphenyl)-1,2,4-oxadiazole 、 4-正庚基苯甲酰氯 在 吡啶 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 [4-[5-[4-(4-Heptylbenzoyl)oxyphenyl]-1,2,4-oxadiazol-3-yl]phenyl] 4-heptylbenzoate
  参考文献：
  名称：

  Banana-Shaped 1,2,4-Oxadiazole Analogues of 1,3,4-Oxadiazoles

  摘要：

  DOI：

  10.1080/10587250108025286
• 作为产物：
  描述：

  3,5-双(4-甲氧基苯基)-1,2,4-恶二唑 在 aluminum tri-bromide 作用下， 以 甲苯 为溶剂， 以95%的产率得到3,5-bis(4-hydroxyphenyl)-1,2,4-oxadiazole
  参考文献：
  名称：

  Banana-Shaped 1,2,4-Oxadiazole Analogues of 1,3,4-Oxadiazoles

  摘要：

  DOI：

  10.1080/10587250108025286

文献信息

• Liquid-crystalline heterodimesogens and ABA-heterotrimesogens comprising a bent 3,5-diphenyl-1,2,4-oxadiazole central unit
  作者：Govindaswamy Shanker、Marko Prehm、Carsten Tschierske

  DOI：10.3762/bjoc.8.54

  日期：——

  dimesogens exhibit broad ranges of cybotactic nematic phases (N(cybA) and N(cybC)), in some cases accompanied by additional mesophases (CybA or SmC) at lower temperature. The combination of the 3,5-diphenyl-1,2,4-oxadiazole unit with one cyanobiphenyl core leads to the removal of tilted smectic and cybotactic nematic phases (SmC, N(cybC)), which are replaced by the nontilted CybA phases and nematic phases composed

  三种新型末端连接的ABA-异三聚体和异二聚体，由弯曲的3,5-二苯基-1,2,4-恶二唑中心单元和一或两个棒状4-氰基联苯核或一个2-苯基-1组成，合成了由柔性间隔物连接的 3,4-噻二唑核，并通过光学偏光显微镜 (PM)、差示扫描量热法 (DSC) 和 X 射线衍射 (XRD) 研究了它们的介晶行为。所有 dimesogens 都表现出广泛的细胞内向列相（N(cybA) 和 N(cybC)），在某些情况下，在较低温度下还伴有额外的中间相（CybA 或 SmC）。3,5-二苯基-1,2,4-恶二唑单元与一个氰基联苯核的组合导致倾斜的近晶相和胞内相向列相（SmC，N（cybC））的去除，它们被非倾斜的 CybA 相和由 SmA 型簇 (N(cybA)) 组成的向列相取代。弯曲核介晶的正交晶胞向列相对于实现正交型双轴向列相特别感兴趣。XRD 和光学观察区分了正交 (N(cybA)) 和偏斜 (N(cybC))
• Structure–Activity Relationship for the Oxadiazole Class of Antibacterials
  作者：Marc A. Boudreau、Derong Ding、Jayda E. Meisel、Jeshina Janardhanan、Edward Spink、Zhihong Peng、Yuanyuan Qian、Takao Yamaguchi、Sebastian A. Testero、Peter I. O’Daniel、Erika Leemans、Elena Lastochkin、Wei Song、Valerie A. Schroeder、William R. Wolter、Mark A. Suckow、Shahriar Mobashery、Mayland Chang

  DOI：10.1021/acsmedchemlett.9b00379

  日期：2020.3.12

  A structure–activity relationship (SAR) for the oxadiazole class of antibacterials was evaluated by syntheses of 72 analogs and determination of the minimal-inhibitory concentrations (MICs) against the ESKAPE panel of bacteria. Selected compounds were further evaluated for in vitro toxicity, plasma protein binding, pharmacokinetics (PK), and a mouse model of methicillin-resistant Staphylococcus aureus

  通过合成72种类似物并确定对ESKAPE细菌的最小抑菌浓度（MIC）来评估恶二唑类抗菌剂的结构活性关系（SAR）。进一步评估了所选化合物的体外毒性，血浆蛋白结合，药代动力学（PK）和耐甲氧西林金黄色葡萄球菌（MRSA）感染的小鼠模型。恶二唑72c显示出有效的体外抗菌活性，显示出低清除率，高分布量和41％的口服生物利用度，并在MRSA感染的小鼠模型中显示出功效。
• 1,2,4-Oxadiazole-Based Bent-Core Liquid Crystals with Cybotactic Nematic Phases
  作者：Govindaswamy Shanker、Marko Prehm、Mamatha Nagaraj、Jagdish K. Vij、Marvin Weyland、Alexey Eremin、Carsten Tschierske

  DOI：10.1002/cphc.201301070

  日期：2014.5.19

  AbstractSeveral series of bent‐core mesogens derived from 3,5‐diphenyl‐1,2,4‐oxadiazole with or without lateral groups and with different length terminal chains at both ends, and polycatenar molecules with three to six alkoxy chains are synthesized and their mesomorphic behaviour is investigated by polarizing microscopy, differential scanning calorimetry, X‐ray diffraction (XRD), dielectric, electro‐optical and second‐harmonic generation (SHG) experiments. Most compounds exhibit broad regions of skewed cybotactic nematic (NcybC) and tilted smectic (SmC) phases with a strong tilt of the aromatic cores (up to 63°), but non‐tilted SmA and NcybA phases are also observed for a compound that has only one terminal chain. The XRD patterns of the nematic phases of most of the compounds investigated indicate a 2D periodicity with short correlation length in the magnetically aligned samples. This is of importance for the general interpretation of the small‐angle XRD splitting patterns typically observed for aligned samples of bent‐core nematic phases. In most nematic phases one current peak is observed in the half period of an applied electric field, though no coherent signal is found in the SHG experiments. Based on additional electro‐optical and dielectric results, the nematic phases are considered to be cybotactic nematic phases with local polar order, and show a dielectric reorientation of the polar domains. Only chiral nematic phases (NcybC*), but not blue phases, are obtained for compounds with one or two chiral (3S)‐3,7‐dimethyloctyloxy tail(s).
• Banana-Shaped 1,2,4-Oxadiazole Analogues of 1,3,4-Oxadiazoles
  作者：Sofia I. Torgova、Ludmila A. Karamysheva、Tatiana A. Geivandova、Alfredo Strigazzi

  DOI：10.1080/10587250108025286

  日期：2001.7.1