(Z)-1-(4-bromostyryl)-1H-imidazole | 1357155-12-4

• 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: (Z)-1-(4-bromostyryl)-1H-imidazole
• 英文别名: 1-(4-bromostyryl)-1H-imidazole；1-[(Z)-2-(4-bromophenyl)ethenyl]imidazole
• CAS: 1357155-12-4
• 化学式: C₁₁H₉BrN₂
• 分子量: 249.11
• InChiKey: FMZBDAICMIIONR-ALCCZGGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对溴碘苯 在 copper(l) iodide 、 1H-苯并三唑-1-甲醇 、 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 生成 (Z)-1-(4-bromostyryl)-1H-imidazole 、 (E)-1-(4-bromostyryl)-1H-imidazole
  参考文献：
  名称：

  Regioselective Preferential Nucleophilic Addition of N-Heterocycles onto Haloarylalkynes over N-Arylation of Aryl Halides

  摘要：

  The study of preferential addition of heterocyclic amines onto halo-substituted arylalkynes over N-arylation under various catalytic conditions is described. The present work supports and confirms the mechanistic pathway of our recent work on the tandem synthesis of indolo- and pyrrolo-[2,1-a]isoquinolines via hydroamination followed by oxidative addition and not vice versa.

  DOI：

  10.1021/ol203491p

文献信息

• Decarboxylative Hydroamination of 3-Arylpropiolic Acids with N-Heterocycles under Transition-Metal-Free Conditions
  作者：Hui Zhang、Weiqing Xie、Xixian Pan、Xiaolong Wan、Xin Yu

  DOI：10.1055/s-0033-1338622

  日期：——

  Abstract A decarboxylative hydroamination cascade reaction of 3-arylpropiolic acids with N-heterocycles under transition-metal-free conditions was developed. 3-Arylpropiolic acids were found to react smoothly with a range of N-heterocycles under the effect of t-BuOK to afford N-vinyl heterocycles in moderate to excellent yields. This reaction represents the first decarboxylative hydroamination of 3-arylpropiolic

  摘要 在无过渡金属条件下，开发了3-芳基丙酸与N-杂环的脱羧加氢胺化级联反应。发现3-芳基丙酸在t -BuOK的作用下与一系列N-杂环平稳反应，以中等至极好的收率提供N-乙烯基杂环。该反应代表在没有过渡金属催化剂的情况下对3-芳基丙酸的第一次脱羧氢化胺化。 在无过渡金属条件下，开发了3-芳基丙酸与N-杂环的脱羧加氢胺化级联反应。发现3-芳基丙酸在t -BuOK的作用下与一系列N-杂环平稳反应，以中等至极好的收率提供N-乙烯基杂环。该反应代表在没有过渡金属催化剂的情况下对3-芳基丙酸的第一次脱羧氢化胺化。
• A stereoselective organic base-catalyzed protocol for hydroamination of alkynes under solvent-free conditions
  作者：Vadym Kozell、Fariba Rahmani、Oriana Piermatti、Daniela Lanari、Luigi Vaccaro

  DOI：10.1016/j.mcat.2018.04.018

  日期：2018.8

  straightforward and atom-economical process for the synthesis of substituted nitrogen-containing alkenes. Herein we report a novel protocol that involves for the first time solvent-free conditions (SolFC) and the use of an organic base, namely 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) to stereoselectively promote the process. The scope of this metal-free protocol

  炔烃的加氢胺化是合成取代的含氮烯烃的直接且原子经济的方法。在这里，我们报告了一种新颖的方案，该方案首次涉及无溶剂条件（SolFC）和有机碱的使用，即2-叔丁基亚氨基-2-二乙氨基-1,3-二甲基过氢-1,3,2-二氮杂磷（BEMP）立体选择性地促进了这一过程。通过广泛的研究评估了该无金属方案的范围，得出的结论是，在大多数情况下，产率和立体选择性值非常高（14个实例，产率高达95％，Z / E高达99％ ）。
• Transition-Metal-Free Synthesis of<i>N</i>-(1-Alkenyl)imidazoles by Potassium Phosphate-Promoted Addition Reaction of Alkynes to Imidazoles
  作者：Linhua Lu、Hong Yan、Defu Liu、Guangwei Rong、Jincheng Mao

  DOI：10.1002/asia.201301173

  日期：2014.1

  The addition reaction of alkynes to N‐heterocycles by simply heating in DMSO with potassium phosphate is reported. Good yields with high stereoselectivity could be achieved for a range of substrates. The scope is quite general for both amines and phenylacetylenes. In addition, internal alkynes and α‐bromostyrene were also examined in this reaction. This process is efficient and useful for the synthesis

  据报道，通过在DMSO中与磷酸钾简单地加热，炔烃与N杂环的加成反应。对于一系列底物，可以实现具有高立体选择性的高产率。对于胺和苯乙炔来说，范围是相当普遍的。此外，在此反应中还检查了内部炔烃和α-溴苯乙烯。该方法对于合成（Z）-N-（1-烯基）咪唑和相关的Z 产物是有效的和有用的。因此，由于咪唑支架的重要性，该反应是有用的。
• Inorganic base-mediated stereoselective hydroamination of arylalkynes with imidazole: An efficient access to N -vinylimidazoles
  作者：Lin-Dong Liu、Zhong-Liang Lei、Hong Wang、Ming Bian、Zhen-Jiang Liu、Jin-Tao Liu、Xiao-Jun Hu

  DOI：10.1016/j.tet.2018.07.022

  日期：2018.8

  A metal-free inorganic base-mediated highly stereoselective hydroamination of arylalkynes with imidazoles has been developed, and the corresponding N-vinylimidazoles were obtained in good yields and with moderate to excellent stereoselectivities (up to 99:1). For the electron rich alkynes, the reaction system of CsOH center dot H2O/NMP/140 degrees C led to the predominant formation of E-addition products, while the reaction system of KOH/NMP/90 degrees C afforded the Z-isomers as the major product. The electron deficient alkynes furnished predominantly the E-addition products in both reaction systems. This study essentially provides a general and an efficient protocol for the synthesis of E-isomer of the N-vinylimidazoles. (C) 2018 Elsevier Ltd. All rights reserved.