1-butyl-5-phenyl-1H-1,2,3-triazole | 15922-74-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-butyl-5-phenyl-1H-1,2,3-triazole
• 英文别名: 3-butyl-4-phenyl-1H-1,2,3-triazole；1-n-butyl-5-phenyl-1H-1,2,3-triazole；1-butyl-5-phenyl-1,2,3-triazole；1-Butyl-5-phenyltriazole；1-butyl-5-phenyltriazole
• CAS: 15922-74-4
• 化学式: C₁₂H₁₅N₃
• 分子量: 201.271
• InChiKey: IOTJVPQWLUYUTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-benzyl-3-butyl-4-phenyl-1H-1,2,3-triazolium iodide 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 以49%的产率得到1-butyl-5-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  通过 1,4-二取代三唑的烷基化脱苄基无钌制备 1,5-二取代三唑

  摘要：

  描述了一种将苄基叠氮化物与末端炔烃的铜催化“点击”偶极环加成反应的 1,4-二取代 1,2,3-三唑产物干净地转化为 1,5-二取代三唑的方法。在微波辐射下 1,4-二取代的 1,2,3-三唑的选择性 N-烷基化之后，通过用叔丁醇钾处理对所得的 1,3,4-三取代的三唑鎓阳离子进行脱苄基化。

  DOI：

  10.1055/s-0035-1562603

文献信息

• A Metal-Free Multicomponent Cascade Reaction for the Regiospecific Synthesis of 1,5-Disubstituted 1,2,3-Triazoles
  作者：Guolin Cheng、Xiaobao Zeng、Jinhai Shen、Xuesong Wang、Xiuling Cui

  DOI：10.1002/anie.201307499

  日期：2013.12.9

  About specifics: A method for the regiospecific synthesis of the title compounds through an unprecedented Michael addition/deacylative diazo transfer/cyclization sequence has been established. The simple and practical method can be used for the modification of primary amines including chiral α‐amines. The process involves the formation three covalent bonds and the cleavage of two covalent bonds (see

  关于细节：已经建立了通过空前的迈克尔加成/去酰基重氮转移/环化序列进行区域特异性合成标题化合物的方法。简单实用的方法可用于伯胺（包括手性α-胺）的修饰。该过程涉及三个共价键的形成和两个共价键的裂解（参见方案，Ts = 4-甲苯磺酰基）。
• A New Method for the Synthesis of 1,5-Disubstituted 1,2,3-Triazoles via Triazolium Salt Intermediates
  作者：Shinichi Koguchi、Kazuki Izawa

  DOI：10.1055/s-0032-1316806

  日期：——

  the birth of my son. His name is Shigemasa. Abstract A new transition metal free procedure for the synthesis of 1,5-disubstituted 1,2,3-triazoles, which proceeds via a triazolium salt intermediate is described. A new transition metal free procedure for the synthesis of 1,5-disubstituted 1,2,3-triazoles, which proceeds via a triazolium salt intermediate is described.

  这项工作是在我儿子出生之际进行的。他的名字叫重政。 抽象 描述了一种新的不含过渡金属的合成方法，该方法可通过三唑鎓盐中间体进行合成1,5-二取代的1,2,3-三唑。 描述了一种新的不含过渡金属的合成方法，该方法可通过三唑鎓盐中间体进行合成1,5-二取代的1,2,3-三唑。
• Rare-earth metal complexes stabilized by amino-phosphineligand. Reaction with mesityl azide and catalysis of the cycloaddition of organic azides and aromatic alkynes
  作者：Bo Liu、Dongmei Cui

  DOI：10.1039/b811363g

  日期：——

  Stoichiometric reactions between mesityl azide (MesN3, Mes = 2,4,6-C6H2Me3) and amino-phosphine ligated rare-earth metal alkyl, LLn(CH2SiMe3)2(THF) (L = (2,6-C6H3Me2)NCH2C6H4P(C6H5)2; Ln = Lu (1a), Sc (1b)), amide, LLu(NH(2,6-C6H3iPr2))2(THF) (2) and acetylide at room temperature gave the amino-phosphazide ligated rare-earth metal bis(triazenyl) complexes, [L(MesN3)]Ln[(MesN3)(CH2SiMe3)]2 (Ln = Lu (3a); Sc (3b)), bis(amido) complex [L(MesN3)]Lu[NH(2,6-C6H3iPr2)]2 (4), and bis(alkynyl) complex (5) (L(MesN3)Lu (CCPh)2)2, respectively. The triazenyl group in 3 coordinates to the metal ion in a rare η2-mode viaNβ and Nγ atoms, generating a triangular metallocycle. The amino-phosphazide ligand, L(MesN3), in 3, 4 and 5 chelates to the metal ion in a η3-mode viaNα and Nγ atoms. In the presence of excess phenylacetylene, complex 3a isomerized to 3′, where the triazenyl group coordinates to the metal ion in a η3 mode viaNα and Nγ atoms. Complexes 1, 2, 3 and 4 have shown an unprecedented catalytic activity towards the cycloaddition of organic azides and aromatic alkynes to afford 1,5-disubstituted 1,2,3-triazoles selectively.

  异亚丙基叠氮化物 (MesN3, Mes = 2,4,6-C6H2Me3) 与氨基膦连接的稀土金属烷基 LLn(CH2SiMe3)2(THF) (L = (2,6-C6H3Me2)NCH2C6H4P(C6H5) 之间的化学计量反应)2; Ln = Lu (1a), Sc (1b)), 酰胺, LLu(NH(2,6-C6H3iPr2))2(THF) (2) 和乙炔在室温下得到氨基磷酰肼连接的稀土金属双(三氮烯基)络合物，[L(MesN3)]Ln[(MesN3)(CH2SiMe3)]2 (Ln = Lu (3a); Sc (3b))，双(酰胺基)络合物[L(MesN3)]Lu[分别为 NH(2,6-C6H3iPr2)]2 (4) 和双(炔基)络合物 (5) (L(MesN3)Lu (CCPh)2)2。 3中的三氮烯基通过Nβ和Nγ原子以稀有的η2-模式与金属离子配位，生成三角形金属环。 3、4和5中的氨基磷酰肼配体L(MesN3)通过Nα和Nγ原子以η3模式与金属离子螯合。在过量苯乙炔存在下，络合物 3a 异构化为 3'，其中三氮烯基通过 Nα 和 Nγ 原子以 η3 模式与金属离子配位。配合物 1、2、3 和 4 对有机叠氮化物和芳香族炔烃的环加成选择性地产生 1,5-二取代的 1,2,3-三唑表现出前所未有的催化活性。
• The effects of ionic liquids on azide-alkyne cycloaddition reactions
  作者：Stephen R. D. George、Gavin L. Edwards、Jason B. Harper

  DOI：10.1039/c0ob00306a

  日期：——

  The effect of a series of ionic liquids on the regioselectivity of the azide-alkyne cycloaddition process was investigated, demonstrating an increased selectivity for the least hindered triazole. The effects of an ionic liquid on the activation parameters for the process were determined and found to be intermediate between coordinating and non-coordinating salts. The importance of knowing the water content of the system is demonstrated by marked changes in the activation parameters in the presence of small concentrations of water.

  研究了一系列离子液体对叠氮-炔环化反应过程的区域选择性的影响，结果表明受阻最小的三唑的选择性增加。测定了离子液体对该过程活化参数的影响，发现其介于配位盐和非配位盐之间。在存在小浓度水的情况下，活化参数会发生明显变化，这表明了解体系中水含量的重要性。
• Rational Design of 4-Aryl-1,2,3-Triazoles for Indoleamine 2,3-Dioxygenase 1 Inhibition
  作者：Ute F. Röhrig、Somi Reddy Majjigapu、Aurélien Grosdidier、Sylvian Bron、Vincent Stroobant、Luc Pilotte、Didier Colau、Pierre Vogel、Benoît J. Van den Eynde、Vincent Zoete、Olivier Michielin

  DOI：10.1021/jm300260v

  日期：2012.6.14

  Indoleamine 2,3-dioxygenase 1 (IDO1) is an important therapeutic target treatment of diseases such as cancer that involve pathological immune escape. Starting from the scaffold of our previously discovered IDO1 inhibitor 4-phenyl-1,2,3-triazole, we used computational structure-based methods to design more potent ligands. This approach yielded highly efficient low molecular weight inhibitors, the most active being of nanomolar potency both in an enzymatic and in a cellular assay, while showing no cellular toxicity and a high selectivity for IDO1 over tryptophan 2,3-dioxygenase (TDO). A quantitative structure-activity relationship based on the electrostatic ligand-protein interactions in the docked binding modes and on the quantum chemically derived charges of the triazole ring demonstrated a good explanatory power for the observed activities.