4-(3-chloropropyl)-1-phenyl-1H-1,2,3-triazole | 1101825-01-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-chloropropyl)-1-phenyl-1H-1,2,3-triazole
• 英文别名: 4-(3-Chloropropyl)-1-phenyltriazole
• CAS: 1101825-01-7
• 化学式: C₁₁H₁₂ClN₃
• 分子量: 221.689
• InChiKey: NXBURCCRZLHRCF-UHFFFAOYSA-N

物化性质

• 沸点：
  378.4±34.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  30.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(3-chloropropyl)-1-phenyl-1H-1,2,3-triazole 在 氘代甲醇 、 N,N-二异丙基乙胺 、 potassium iodide 作用下， 以 氘代乙腈 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Oxidative Esterification of Aldehydes Using Mesoionic 1,2,3-Triazolyl Carbene Organocatalysts

  摘要：

  The synthesis and catalytic activity of a new class of 1,2,3-triazolyl N-heterocyclic carbene organocatalysts is described. These new catalysts chemoselectively facilitate the oxidative esterification of aldehydes. NMR acidity studies show an inverse correlation between triazolium acidity and reactivity. Kinetic studies show that the resting state of the catalyst involves a NHC-aldehyde adduct. A catalytically active intermediate was synthesized and characterized by X-ray diffraction as the initial carbene aldehyde adduct

  DOI：

  10.1021/ol501458p
• 作为产物：
  描述：

  苯胺 在 盐酸 、 copper diacetate 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 sodium nitrite 作用下， 以 水 、 乙腈 为溶剂， 反应 1.5h， 生成 4-(3-chloropropyl)-1-phenyl-1H-1,2,3-triazole
  参考文献：
  名称：

  Oxidative Esterification of Aldehydes Using Mesoionic 1,2,3-Triazolyl Carbene Organocatalysts

  摘要：

  The synthesis and catalytic activity of a new class of 1,2,3-triazolyl N-heterocyclic carbene organocatalysts is described. These new catalysts chemoselectively facilitate the oxidative esterification of aldehydes. NMR acidity studies show an inverse correlation between triazolium acidity and reactivity. Kinetic studies show that the resting state of the catalyst involves a NHC-aldehyde adduct. A catalytically active intermediate was synthesized and characterized by X-ray diffraction as the initial carbene aldehyde adduct

  DOI：

  10.1021/ol501458p

文献信息

• Heteroleptic Bis(N-heterocyclic carbene)Copper(I) Complexes: Highly Efficient Systems for the [3+2] Cycloaddition of Azides and Alkynes
  作者：Faïma Lazreg、Alexandra M. Z. Slawin、Catherine S. J. Cazin

  DOI：10.1021/om3006195

  日期：2012.11.26

  The first examples of heteroleptic bis-N-heterocyclic carbene (NHC) copper(I) complexes and a mixed NHC–phosphine Cu complex are reported. These complexes are easily synthesized from the reaction of [Cu(OH)(NHC)] with various imidazol(idin)ium or phosphonium tetrafluoroborate salts. These cationic heteroleptic bis-NHC Cu complexes are highly active systems for the azide–alkyne cycloaddition leading

  报告了杂合双-N-杂环卡宾（NHC）铜（I）配合物和NHC-膦铜混合配合物的第一个例子。这些配合物很容易从[Cu（OH）（NHC）]与各种咪唑（id啶）鎓或四氟硼酸phospho盐的反应中合成。这些阳离子型杂合双NHC铜络合物是叠氮化物-炔烃环加成反应的高活性体系，导致形成1,2,3-三唑。研究了这种转变的机理，并且收集到的信息表明，在催化过程中，只有一个NHC保持与金属中心的配位。
• CYCLOADDITION OF AZIDES AND ALKYNES
  申请人：Nolan Steven P.

  公开号：US20090069569A1

  公开（公告）日：2009-03-12

  This invention provides a process which comprises contacting, in a reaction zone, at least one organic azide, at least one alkyne, and at least one N-heterocyclic carbene copper compound in which the ligands are either (i) a halide and an N-heterocyclic carbene or (ii) two N-heterocyclic carbenes and a BF 4 − or PF 6 − anion, to form a 1,2,3-triazole in which at least the 1 and 4 positions each has a substituent. The N-heterocyclic carbene either an imidazol-2-ylidene in which the 1 and the 3 positions each has a substituent which has at least one carbon atom, or a 4,5-dihydro-imidazol-2-ylidene in which the 1 and the 3 positions each has a substituent which has at least one carbon atom.

  这项发明提供了一种方法，其中包括在反应区域中接触至少一种有机叠氮化合物、至少一种炔烃以及至少一种N-杂环卡宾铜化合物，其中配体可以是（i）一种卤素和一种N-杂环卡宾，或者（ii）两种N-杂环卡宾和一个BF4−或PF6−阴离子，以形成一种1,2,3-三唑，其中至少1和4位置各具有一个取代基。N-杂环卡宾可以是1,3位置各具有至少一个碳原子的咪唑-2-基卡宾，或者是1,3位置各具有至少一个碳原子的4,5-二氢咪唑-2-基卡宾。
• [(NHC)₂Cu]X Complexes as Efficient Catalysts for Azide-Alkyne Click Chemistry at Low Catalyst Loadings
  作者：Silvia Díez-González、Steven P. Nolan

  DOI：10.1002/anie.200803289

  日期：2008.11.3