1-苄基-4-[2-(4-甲氧基苯基)乙炔基]三唑 | 920282-82-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-苄基-4-[2-(4-甲氧基苯基)乙炔基]三唑
• 英文名称: 1-benzyl-4-(4-methoxyphenylethynyl)-1H-[1,2,3]triazole
• 英文别名: 4-[(4-methoxyphenyl)ethynyl]-1-benzyl-1H-1,2,3-triazole；1-Benzyl-4-[(4-methoxyphenyl)ethynyl]-1H-1,2,3-triazole；1-benzyl-4-[2-(4-methoxyphenyl)ethynyl]triazole
• CAS: 920282-82-2
• 化学式: C₁₈H₁₅N₃O
• 分子量: 289.337
• InChiKey: FPJJWELIFMJLMY-UHFFFAOYSA-N

物化性质

• 熔点：
  159-162 °C
• 沸点：
  498.5±55.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  39.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  ((4-methoxyphenyl)buta-1,3-diyn-1-yl)trimethylsilane 在 水 、 potassium carbonate 、 copper(II) sulfate 、 维生素 C 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 1-苄基-4-[2-(4-甲氧基苯基)乙炔基]三唑
  参考文献：
  名称：

  Regioselective Trapping of Terminal Di-, Tri-, and Tetraynes with Benzyl Azide

  摘要：

  The reaction of benzyl azide with terminal di-, tri-, and tetraynes appended with a range of functional groups has been explored. Standard reaction conditions for BnN3 catalyzed by CuSO(4)(.)5H(2)O gave alkynyl, butadiynyl, and hexatriynyl triazoles in moderate to good yields. The reaction proceeds regioselectively as determined by the X-ray crystallographic analysis of three derivatives (1c, 1d, and 3c), and no evidence of multiple azide addition to the polyyne framework is observed.

  DOI：

  10.1021/ol062522a

文献信息

• Synthesis, Structures and Reactions of Isolable Terminal Aryl/Biaryl-butadiynes (Ar-C≡C-C≡CH)
  作者：Kara West、Laura N. Hayward、Andrei S. Batsanov、Martin R. Bryce

  DOI：10.1002/ejoc.200800618

  日期：2008.10

  The synthesis and isolation is reported of five terminal aryl/biaryl-butadiynes, Ar–C≡C–C≡CH, (5a–c, 10a and 10b) from 2-methyl-6-aryl/biaryl-hexa-3,5-diyn-2-ol precursors [Ar–C≡C–C≡C–C(Me)2OH; Ar = 2-MeOC6H4, 3-MeOC6H4, 4-MeOC6H4, 2-phenylpyridin-5-yl, 3-phenylpyridin-2-yl, respectively]. The X-ray crystal structures have been obtained for compounds 5c and 10a. Surprisingly, no ≡C–H···X (X = N or

  据报道，从 2-甲基-6-芳基/联芳基-六-3,5 合成和分离五个末端芳基/联芳基-丁二炔，Ar-C≡C-C≡CH，（5a-c、10a 和 10b） -diyn-2-ol 前体 [Ar–C≡C–C≡C–C(Me)2OH; Ar = 2-MeOC6H4、3-M​​eOC6H4、4-MeOC6H4、2-苯基吡啶-5-基、3-苯基吡啶-2-基]。已获得化合物 5c 和 10a 的 X 射线晶体结构。令人惊讶的是，5c 和10a 的晶体中不存在≡C–H…X（X = N 或O）氢键。这些结构说明了一个事实，即≡C–H···X 氢键并不总是晶体工程的可靠工具。钯催化的 5c 与 2-碘嘧啶的交叉偶联得到不对称的 1,4-二芳基丁二炔衍生物 12；5c 和 10a 与苄基叠氮化物的铜催化反应区域选择性地进行，得到炔基三唑 13 和 14。（© Wiley-VCH Verlag GmbH & Co. KGaA，
• An easy access to unsymmetrically substituted 4,4′-bi-1,2,3-triazoles
  作者：Vito Fiandanese、Daniela Bottalico、Giuseppe Marchese、Angela Punzi、Francesca Capuzzolo

  DOI：10.1016/j.tet.2009.10.078

  日期：2009.12

  A convenient synthesis of 4-alkynyl-1,2,3-triazoles and novel unsymmetrically substituted 4,4'-bi-1,2,3-triazole derivatives has been devised starting from easily available 1-trimethylsilyi-1,3-butadiyne. The starting compound was reacted with several azides, leading to 4-(silylalkynyl)-1,2,3-triazoles, which were easily transformed into 4-arylalkynyl-1,2,3-triazoles by a Pd catalyzed coupling reaction with aryl halides, or into novel 4,4'-bi-1,2,3-triazole derivatives by a subsequent cyclization reaction with azides. (C) 2009 Elsevier Ltd. All rights reserved.
• Reactions of Terminal Polyynes with Benzyl Azide
  作者：Thanh Luu、Boris J. Medos、Erin R. Graham、Danielle M. Vallee、Robert McDonald、Michael J. Ferguson、Rik R. Tykwinski

  DOI：10.1021/jo101870y

  日期：2010.12.17

  Terminal di-, tri-, tetra-, and pentaynes substituted with a variety of functional groups react with benzyl azide in the presence of CuSO4 center dot 5H(2)O and ascorbic acid to give derivatives of 4-ethynyl-, 4-butadiynyl-, 4-hexatriynyl-, and 4-octatetraynyl-,2,3-triazoles in moderate to good yields. These reactions appear to proceed regioselectively, and functionalization occurs exclusively at the terminal alkyne moiety. As well, no evidence of multiple azide additions to the polyyne framework is observed. X-ray crystallographic analysis of nine derivatives is used to document the regioselectivity of the reaction as well as outline structural characteristics of the 1,2,3-triazole products.
• Regioselective Trapping of Terminal Di-, Tri-, and Tetraynes with Benzyl Azide
  作者：Thanh Luu、Robert McDonald、Rik R. Tykwinski

  DOI：10.1021/ol062522a

  日期：2006.12.1

  The reaction of benzyl azide with terminal di-, tri-, and tetraynes appended with a range of functional groups has been explored. Standard reaction conditions for BnN3 catalyzed by CuSO(4)(.)5H(2)O gave alkynyl, butadiynyl, and hexatriynyl triazoles in moderate to good yields. The reaction proceeds regioselectively as determined by the X-ray crystallographic analysis of three derivatives (1c, 1d, and 3c), and no evidence of multiple azide addition to the polyyne framework is observed.