2-phenyl-5-piperidino-1,2,3-triazol-4-carbonitril | 134425-98-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-5-piperidino-1,2,3-triazol-4-carbonitril
• 英文别名: 2-phenyl-4-cyano-5-piperidin-1-yl-2H-[1,2,3]triazole；2-Phenyl-5-(1-piperidinyl)-4-triazolecarbonitrile；2-phenyl-5-piperidin-1-yltriazole-4-carbonitrile
• CAS: 134425-98-2
• 化学式: C₁₄H₁₅N₅
• 分子量: 253.307
• InChiKey: MORDGEGZZASYEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-phenyl-5-piperidino-1,2,3-triazol-4-carbonitril 以80%的产率得到
  参考文献：
  名称：

  Elnagdi Mohamed Hilmy, Elghandour Ahmed Hafez Hussien, Harb Abdel Fattah +, Heterocycles, 38 (1994) N 4, S 739-750

  摘要：

  DOI：
• 作为产物：
  描述：

  (苯基亚肼基)丙二腈 在 吡啶 、 copper (I) acetate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-phenyl-5-piperidino-1,2,3-triazol-4-carbonitril
  参考文献：
  名称：

  Synthese und Reaktionen von 2-Arylhydrazono-2-cyan-N,N-dialkyl-acetamidinen

  摘要：

  The title compounds 3 were synthesized by reaction of arlyhydrazono-malononitriles 1 with secondary amines and used for subsequent cyclization reactions. Thus, 3 undergoes cyclooxidation by treatment with CuSO4/pyridine to form the 5-dialkylamino-2-aryl-1,2,3-triazolo-4-carbonitriles 4. From 4 a and hydrazine hydrate/DMF the 4-(1,3,4-triazolyl-5)-1,2,3-triazole 5 c is obtainable. The chloroacetylation of 3 is accompanied by hydrolysis of the amino group to yield the arylhydrazono-N-chloracetyl cyanoacetamides 6. The quaternisation of 6 with pyridins is followed by the Thorpe cyclization to form the 4-amino-5-arylazo-6-hydroxy-3-pyridinio-pyrid-2-on-chlorides 8, useful as cationic dyes. The reaction of 3 with trichloroacetonitriles yields the 5-arylazo-4-imino-2-trichlormethyl-1,4-dihydropyrimidines 10 a-c which can be converted into the 5-arylazo-2-hydrazino-pyrimidine derivatives 10 d-f.From 10 d the 6-phenylazo-triazolo[4,3-a]pyrimidine derivative 11 is obtainable. From 3 and phenylisothiocyanate the 5-arylazo-4-imino-1,4-dihydropyrimidin-2-thiones 12 arise. The structures were investigated by C-13-NMR-spectroscopy.

  DOI：

  10.1007/bf00809365

文献信息

• 5-Amino-2-aryl-1,2,3-triazol-4-carboxylic acids: Synthesis, photophysical properties, and application prospects
  作者：Nikita E. Safronov、Timur O. Fomin、Artem S. Minin、Lozan Todorov、Irena Kostova、Enrico Benassi、Nataliya P. Belskaya

  DOI：10.1016/j.dyepig.2020.108343

  日期：2020.7

  present an effective strategy for the synthesis of novel 2-aryl-1,2,3-triazol-4-carboxylic acids (ATAs). The behavior of ATAs in different solvents showed that these new 1,2,3-triazole derivatives had bright blue fluorescence with excellent quantum yields, large Stokes shifts, and prolonged fluorescence lifetimes. Their photophysical and physicochemical properties showed extra sensitivity to both structural

  为了扩大小分子杂环的高活性荧光团家族，我们提出了一种新型2-芳基-1,2,3-三唑-4-羧酸（ATAs）合成的有效策略。ATA在不同溶剂中的行为表明，这些新的1,2,3-三唑衍生物具有明亮的蓝色荧光，具有出色的量子产率，大的斯托克斯位移和延长的荧光寿命。它们的光物理和理化性质对结构变化和微环境都表现出额外的敏感性，通常伴随着量子产率的显着变化。ATA对不同pH的响应取决于三唑环C5原子上氨基的结构。对于带有叔氨基的ATA，pKa值为7.65–8.08。相反，带有仲烷基胺的ATA的pKa值在3.20-3.52之间。量子力学方法被用来理解潜在的转变并解释获得的实验数据。在合成的化合物中，观察到聚集诱导的发射增强（AIEE）行为，具有潜在的应用作为监测和控制pH值的传感器。ATA在酸性和碱性pH值之间的可逆性及其毒性支持其在生物学研究中的实时使用。具有潜在的应用作为监测和控制pH值的传感器。AT
• Multistep Flow Synthesis of 5-Amino-2-aryl-2<i>H</i>-[1,2,3]-triazole-4-carbonitriles
  作者：Jérôme Jacq、Patrick Pasau

  DOI：10.1002/chem.201402074

  日期：2014.9.15

  flow synthesis for the preparation of various 2‐aryl‐1,2,3‐triazoles. Our strategy involves a three‐step synthesis under continuous‐flow conditions that starts from the diazotization of anilines and subsequent reaction with malononitrile, followed by nucleophilic addition of amines, and finally employs a catalytic copper(II) cyclization. Potential safety hazards associated with the formation of reactive

  1,2,3-三唑已成为当代药物化学中最重要的杂环之一。铜催化的惠斯根环加成反应的发展已使1取代的1,2,3-三唑的有效合成成为可能。但是，仅有几种方法可用于选择性制备2-取代的1,2,3-三唑异构体。在这种情况下，我们决定开发一种高效的流动合成方法，以制备各种2-芳基-1,2,3-三唑。我们的策略涉及在连续流动条件下的三步合成，该过程从苯胺的重氮化开始，然后与丙二腈反应，然后亲核加成胺，最后采用催化铜（II）环化。在线猝灭已经解决了与反应性重氮物质形成相关的潜在安全隐患。使用流动设备可以通过可靠地控制反应条件实现可靠的按比例放大过程。2-取代的1,2,3-三唑的合成具有良好的收率和优异的选择性，因此提供了1,2,3-三唑的广泛选择。
• SCHAFER, H.;GEWALD, K.;BELLMANN, P.;GRUNER, M., MONATSH. CHEM., 122,(1991) N, C. 195-207
  作者：SCHAFER, H.、GEWALD, K.、BELLMANN, P.、GRUNER, M.

  DOI：——

  日期：——
• Elnagdi Mohamed Hilmy, Elghandour Ahmed Hafez Hussien, Harb Abdel Fattah +, Heterocycles, 38 (1994) N 4, S 739-750
  作者：Elnagdi Mohamed Hilmy, Elghandour Ahmed Hafez Hussien, Harb Abdel Fattah +

  DOI：——

  日期：——
• Synthese und Reaktionen von 2-Arylhydrazono-2-cyan-N,N-dialkyl-acetamidinen
  作者：H. Sch�fer、K. Gewald、P. Bellmann、M. Gruner

  DOI：10.1007/bf00809365

  日期：1991.3

  The title compounds 3 were synthesized by reaction of arlyhydrazono-malononitriles 1 with secondary amines and used for subsequent cyclization reactions. Thus, 3 undergoes cyclooxidation by treatment with CuSO4/pyridine to form the 5-dialkylamino-2-aryl-1,2,3-triazolo-4-carbonitriles 4. From 4 a and hydrazine hydrate/DMF the 4-(1,3,4-triazolyl-5)-1,2,3-triazole 5 c is obtainable. The chloroacetylation of 3 is accompanied by hydrolysis of the amino group to yield the arylhydrazono-N-chloracetyl cyanoacetamides 6. The quaternisation of 6 with pyridins is followed by the Thorpe cyclization to form the 4-amino-5-arylazo-6-hydroxy-3-pyridinio-pyrid-2-on-chlorides 8, useful as cationic dyes. The reaction of 3 with trichloroacetonitriles yields the 5-arylazo-4-imino-2-trichlormethyl-1,4-dihydropyrimidines 10 a-c which can be converted into the 5-arylazo-2-hydrazino-pyrimidine derivatives 10 d-f.From 10 d the 6-phenylazo-triazolo[4,3-a]pyrimidine derivative 11 is obtainable. From 3 and phenylisothiocyanate the 5-arylazo-4-imino-1,4-dihydropyrimidin-2-thiones 12 arise. The structures were investigated by C-13-NMR-spectroscopy.