2-[5-(2-氨基苯基)-1,3,4-恶二唑-2-基]苯胺 | 19542-04-2

• 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-[5-(2-氨基苯基)-1,3,4-恶二唑-2-基]苯胺
• 英文名称: 2,5-bis(2-aminophenyl)-1,3,4-oxadiazole
• 英文别名: 2,5-di(2-aminophenyl)-1,3,4-oxadiazole；2,5-di(o-aminophenyl)-1,3,4-oxadiazole；2.5-Bis-<2-amino-phenyl>-1.3.4-oxadiazol；1,3,4-OXADIAZOLE, 2,5-BIS(o-AMINOPHENYL)-；2-[5-(2-aminophenyl)-1,3,4-oxadiazol-2-yl]aniline
• CAS: 19542-04-2
• 化学式: C₁₄H₁₂N₄O
• 分子量: 252.275
• InChiKey: WEQLMOBWMDHBIA-UHFFFAOYSA-N

物化性质

• 熔点：
  155-160 °C(Solv: ethanol (64-17-5))
• 沸点：
  496.8±55.0 °C(Predicted)
• 密度：
  1.301±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 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：
  91
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[5-(2-氨基苯基)-1,3,4-恶二唑-2-基]苯胺 生成 2,5-二苯基-1,3,4-恶二唑
  参考文献：
  名称：

  Krasovitskii,B.M. et al., Journal of general chemistry of the USSR, 1961, vol. 31, p. 2107 - 2109

  摘要：

  DOI：
• 作为产物：
  描述：

  双(2-硝基苯甲酰肼) 在 sodium disulfide 、 五氯化磷 作用下， 以 吡啶 、 水 为溶剂， 生成 2-[5-(2-氨基苯基)-1,3,4-恶二唑-2-基]苯胺
  参考文献：
  名称：

  Krasovitskii,B.M. et al., Journal of general chemistry of the USSR, 1961, vol. 31, p. 2107 - 2109

  摘要：

  DOI：

文献信息

• A new synthesis of symmetrical 2,5-disubstituted 1,3,4-oxadiazoles
  作者：Fouad Bentiss、Michel Lagrenée

  DOI：10.1002/jhet.5570360433

  日期：1999.7

  Several new 2,5-disubstituted 1,3,4-oxadiazoles have been synthesized in good yields by reaction of aromatic acids with hydrazine dihydrochloride in a mixture of orthophosphoric acid, phosphorus pentoxide and, in general, with addition of phosphorus oxychloride to the reaction mixture. The structures of new oxadiazoles derivatives were confirmed by analytical and spectral data.

  通过芳族酸与肼二盐酸盐在正磷酸，五氧化二磷的混合物中反应，以及通常在反应中加入三氯氧化磷，已经以高收率合成了几种新的2,5-二取代的1,3,4-恶二唑混合物。通过分析和光谱数据证实了新的恶二唑衍生物的结构。
• Electrosynthesis of 2-(1,3,4-Oxadiazol-2-yl)aniline Derivatives with Isatins as Amino-Attached C1 Sources
  作者：Peng Qian、Zhenghong Zhou、Li Wang、Zhicheng Wang、Zhongwei Wang、Zhenlei Zhang、Liangquan Sheng

  DOI：10.1021/acs.joc.0c01700

  日期：2020.10.16

  intramolecular decarboxylative coupling reaction for the construction of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives was developed from readily available isatins and hydrazides by virtue of electrochemistry. In this reaction, isatins were employed as amino-attached C1 sources, providing a variety of 2-(1,3,4-oxadiazol-2-yl)aniline derivatives with moderate to good yields.

  通过电化学从易得的靛红和酰肼中开发出用于构建2-（1,3,4-恶二唑-2-基）苯胺衍生物的分子内脱羧偶联反应。在该反应中，靛红被用作氨基连接的C1来源，以中等至良好的产率提供了各种2-（1,3,4-恶二唑-2-基）苯胺衍生物。
• Synthesis of Pyridine-Based 1,3,4-Oxadiazole Derivative as Fluorescence Turn-On Sensor for High Selectivity of Ag+
  作者：Chunling Zheng、Ailin Yuan、Zhengyu Zhang、Hong Shen、Shuyuan Bai、Haibo Wang

  DOI：10.1007/s10895-013-1213-y

  日期：2013.7

  An oxadiazole derivative(OXD) containing symmetrical pyridine-2-formamidophenyl-binded moiety was synthesised as fluorescence turn-on sensor OA1. Its ultraviolet–visible(UV–vis) and fluorescent spectra(FS) gave prominent fluorescence enhancement only for monovalent silver ion(Ag+) in HEPES buffer solution (10 mM, pH = 7.0, DMF-H2O, 9:1, v/v), which indicated the photo-induced electron transfer(PET) occurred from the donor of pyridine-2-formamidophenyl group to oxadiazole fluorophore. The present study demonstrated that OA1 was a viable candidate as fluorescent receptor for a new Ag+ sensor. And the results of fluorescent spectral titration showed this sensor formed 1:1 complex with Ag+.

  一种含有对称吡啶-2-甲脒苯基结合基的噁二唑衍生物（OXD）被合成为荧光开启传感器 OA1。其紫外可见光谱（UV-vis）和荧光光谱（FS）仅对 HEPES 缓冲溶液（10 mM，pH = 7.0，DMF-H2O，9:1，v/v）中的一价银离子（Ag+）有明显的荧光增强，这表明从吡啶-2-甲脒苯基的供体到噁二唑荧光团之间发生了光诱导电子转移（PET）。本研究表明，OA1 是新型 Ag+ 传感器荧光受体的可行候选材料。荧光光谱滴定结果表明，该传感器与 Ag+ 形成了 1:1 的复合物。
• Multi-analyte, ratiometric and relay recognition of a 2,5-diphenyl-1,3,4-oxadiazole-based fluorescent sensor through modulating ESIPT
  作者：Lijun Tang、Zhuxuan Zheng、Zhenlong Huang、Keli Zhong、Yanjiang Bian、Raju Nandhakumar

  DOI：10.1039/c4ra16347h

  日期：——

  A novel 2,5-diphenyl-1,3,4-oxadiazole-based fluorescent sensor for multi-analyte, ratiometric and relay recognition of a through modulating ESIPT has been developed.

  一种基于2,5-二苯基-1,3,4-噁二唑的荧光传感器已被开发出来，用于多种分析物的比率和中继识别，通过调节ESIPT实现。
• Bimetallic Reactivity. On the Use of Oxadiazoles as Binucleating Ligands
  作者：Christopher Incarvito、Arnold L. Rheingold、C. Jin Qin、Anna L. Gavrilova、B. Bosnich

  DOI：10.1021/ic0012773

  日期：2001.3.1

  Two (1,3,4)-oxadiazole ligands have been prepared. In one case the oxadiazole ring is flanked by two o-aniline groups, and in the other case it is an extension of the first where the amines are condensed with 2-picolyl groups. A monometallic copper(II) complex of the former has been prepared, and its crystal structure was determined. A number of bimetallic copper(II), cobalt(II), and nickel(II) complexes

  已经制备了两个（1,3,4）-恶二唑配体。在一种情况下，恶二唑环的侧面为两个邻苯胺基，而在另一种情况下，则是胺与2-甲基吡啶基缩合的第一个环的延伸。制备了前者的单金属铜（II）配合物，并确定了其晶体结构。制备并分离了双去质子化的后者配体的许多双金属铜（II），钴（II）和镍（II）配合物。报道了带有两个乙酸酯桥的钴（II）配合物的晶体结构。这项工作表明，很少使用的恶二唑环可有效地用于生成双金属配合物。