3-butyl-1-methyl-5-phenyl-1H-1,2,3-triazol-3-ium iodide | 1266238-80-5

• 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-butyl-1-methyl-5-phenyl-1H-1,2,3-triazol-3-ium iodide
• 英文别名: 1-butyl-3-methyl-4-phenyl-1H-1,2,3-triazolium iodide
• CAS: 1266238-80-5
• 化学式: C₁₃H₁₈N₃*I
• 分子量: 343.211
• InChiKey: BUNDNUYORQIZIK-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.82
• 重原子数：
  17.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-butyl-1-methyl-5-phenyl-1H-1,2,3-triazol-3-ium iodide 以 二氯甲烷 为溶剂， 反应 32.0h， 生成 [{Pd(μ-Cl)Cl(1-butyl-3-methyl-4-phenyl-1H-1,2,3-triazol-5-ylidene)}₂]
  参考文献：
  名称：

  二聚钯1,2,3-三唑-5-亚烷基络合物–铃木偶联的合成，结构，反应性和催化性能†

  摘要：

  通式[{Pd（μ-Cl）Cl（tzNHC）} 2 ]的新二聚钯1,2,3-三唑-5-亚烷基配合物（tzNHC = 1-甲磺酰基-3-甲基-4-苯基-1 H -1,2,3-三唑-5-亚叉基; 1-己基-3-甲基-4-苯基-1 H -1,2,3-三唑-5-亚叉基和1-丁基-3-甲基-4 -苯基-1 H合成了1,2,3-3-三唑-5-亚烷基并通过光谱法，X射线分析和DFT计算对其进行了表征。对于均三取代的配合物，获得了顺式和反式异构体的晶体结构。在过量的4-甲苯基硼酸的存在下，观察到tzNHC配体作为5-甲苯基三唑鎓盐从钯配位球中丢失。该络合物是在芳基硼酸与芳基溴化物的偶联中具有催化活性的钯物质的前体。

  DOI：

  10.1039/c8nj00981c
• 作为产物：
  描述：

  苯乙炔 在 sodium azide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 96.0h， 生成 3-butyl-1-methyl-5-phenyl-1H-1,2,3-triazol-3-ium iodide
  参考文献：
  名称：

  PEPPSI-type palladium 1,2,3-triazolin-5-ylidene complexes – Synthesis, structure and catalytic properties in Suzuki-Miyaura coupling

  摘要：

  Palladium complexes of the general formula [PdCl2(tzNHC)(pyridine)] bearing a series 1,2,3-triazolin-5-ylidene (tzNHC) ligands were synthesized and characterized by spectroscopic methods and X-ray analysis. Complexes exhibit catalytic activity in the Suzuki-Miyaura coupling of boronic acids with aryl bromides.

  DOI：

  10.1016/j.ica.2018.06.028

文献信息

• Wingtip substituents tailor the catalytic activity of ruthenium triazolylidene complexes in base-free alcohol oxidation
  作者：Daniel Canseco-Gonzalez、Martin Albrecht

  DOI：10.1039/c3dt32939a

  日期：——

  A series of RuII (η6-arene) complexes with 1,2,3-triazolylidene ligands comprising different aryl and alkyl wingtip groups have been prepared and characterized by NMR spectroscopy, microanalysis, and in one case by X-ray diffraction. All complexes are active catalyst precursors for the oxidation of alcohols to the corresponding aldehydes/ketones without the need of an oxidant or base as additive. The wingtip groups have a direct impact on the catalytic activity, alkyl wingtips providing the most active species while aryl wingtip groups induce lower activity. An N-bound phenyl group was the most inhibiting wingtip group due to cyclometalation. Arene dissociation was observed as a potential catalyst deactivation pathway.

  一系列包含不同芳基和烷基侧翼基团的1,2,3-三唑啉二烯配体的RuII（η6-芳烃）配合物已通过NMR光谱、微量分析以及在一种情况下的X射线衍射得以制备和表征。所有配合物均是活性的醇氧化为相应醛/酮的催化剂前体，无需添加氧化剂或碱。侧翼基团对催化活性有直接影响，烷基侧翼基团提供最活跃的物种，而芳基侧翼基团导致较低的活性。氮键合的苯基是抑制性最强的侧翼基团，因为环金属化作用。观察到芳烃解离作为潜在的催化剂失活途径。
• Symmetric triazolylidene Ni(II) complexes applied as oxidation catalysts
  作者：Siyabonga G. Mncube、Muhammad D. Bala

  DOI：10.1016/j.poly.2018.10.036

  日期：2019.1

  carbene ligands (NHC) [ trans- X 2 Ni(NHC) 2 ] (X = Cl, I) bearing linear straight chain alkyl wingtip substituents have been synthesised and fully characterised. Single crystal XRD data revealed symmetrically aligned Ni(II) centres within square planar coordination of trans halide, trans NHC ligands. The complexes were used for the catalytic oxidation of alkanes under mild conditions in conjunction with

  摘要合成了一组带有线性直链烷基翼尖取代基的N-杂环卡宾配体（NHC）[反式X 2 Ni（NHC）2]（X = Cl，I）的相关Ni（II）配合物。 。单晶XRD数据揭示了反式卤化物，反式NHC配体的方形平面配位中对称排列的Ni（II）中心。该络合物与叔丁基氢过氧化物作为氧化剂一起在温和条件下用于烷烃的催化氧化。在优化的反应条件下，催化结果表明环己烷和正辛烷分别具有约15％和19％的良好活性。此外，显示出催化体系对于将直链醇氧化为相应的酮非常有效。
• Mesoionic Triazolylidene Nickel Complexes: Synthesis, Ligand Lability, and Catalytic C–C Bond Formation Activity
  作者：Yingfei Wei、Ana Petronilho、Helge Mueller-Bunz、Martin Albrecht

  DOI：10.1021/om500593s

  日期：2014.10.27

  of triazolylidene (trz) nickel(II) complexes [NiCpX(trz)] was synthesized by a direct metalation of the corresponding triazolium salt with nickelocene, NiCp2. While at short reaction times and in the presence of a coordinating anion X the mono-carbene complex is preferably formed, long reaction times induce the gradual transformation of [NiCpX(trz)] to the bis-carbene complexes [Ni(Cp)(trz)2]+. Kinetic

  通过将相应的三唑鎓盐与新世代NiCp 2直接金属化，合成了一组三唑基（trz）镍（II）配合物[NiCpX（trz）] 。虽然在短的反应时间和在配位阴离子X的存在下，优选形成单碳烯配合物，但长的反应时间会引起[NiCpX（trz）]逐渐转变为双碳烯配合物[Ni（Cp）（trz） ）2 ] +。动力学分析为涉及从[NiCpX（trz）]到三碳烯络合物的三唑基亚离解的连续途径提供了有力的支持。在真空中加热配合物[NiCpI（trz）]时，在固态反应中观察到类似的卡宾转移，这导致歧化成[NiI 2（trz）2]和NiCp 2，证实Ni–C（trz）键在动力学上不稳定。配合物[Ni（Cp）（trz）2 ] +和[NiCpX（trz）]都是芳基溴化物和苯基硼酸的Suzuki-Miyaura交叉偶联的有效催化剂前体，转换频率超过228 h –1。在单独的实验中确定，在较短的反应时间后，复合物降解会阻止
• Synthesis and Tunability of Abnormal 1,2,3-Triazolylidene Palladium and Rhodium Complexes
  作者：Aurélie Poulain、Daniel Canseco-Gonzalez、Rachel Hynes-Roche、Helge Müller-Bunz、Oliver Schuster、Helen Stoeckli-Evans、Antonia Neels、Martin Albrecht

  DOI：10.1021/om101076u

  日期：2011.3.14

  Palladation of N3-alkylated 1,2,3-triazolium salts with Pd(OAc)(2) afforded a mu(2)-I-2 bridged bimetallic complex [Pd(trz)I-2](2) and monometallic bis(carbene) complexes Pd(trz)(2)I-2 as a mixture of trans and cis isomers (trz = 1,2,3-triazol-5-ylidene). Addition of excess halide or modification of the palladation procedure from direct functionalization to a transmetalation sequence involving a silver intermediate allowed for chemoselective formation of the bis(carbene) complex, while subsequent anion metathesis with NaI produced the monometallic bis(carbene) complexes exclusively. Modification of the wingtip group had little influence on the metalation to palladium or rhodium(I) via transmetalation. According to NMR analysis using delta(C) and (1)J(Rh-C), subtle but noticeable tunability of the metal electronic properties was identified. In addition, phenyl wingtip groups as N-substituents in the triazolylidene ligands were susceptible to cyclopalladation in the presence of NaOAc and are thus not chemically inert.