4-(2-氯乙炔基)苯甲腈 | 919791-41-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2-氯乙炔基)苯甲腈
• 英文名称: 4-(chloroethynyl)benzonitrile
• 英文别名: 4-(2-chloroethynyl)benzonitrile
• CAS: 919791-41-6
• 化学式: C₉H₄ClN
• 分子量: 161.59
• InChiKey: QUTLBGVEWPCLLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-乙炔基-4-硝基苯 、 4-(2-氯乙炔基)苯甲腈 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以58%的产率得到4-[(4-nitrophenyl)buta-1,3-diyn-1-yl]benzonitrile
  参考文献：
  名称：

  Unsymmetrical Coupling of 1-Chloroalkynes and Terminal Alkynes under ­Experimental Sonogashira Conditions

  摘要：

  The coupling of a 1-chloroalkyne and a terminal alkyne to furnish a 1,3-butadiyne under experimental Sonogashira conditions is investigated. Through competition experiments, it is found that 1-chloroalkynes provide cross-coupling products as efficiently (or slightly better) in comparison with iodobenzenes, and almost as effectively as vinyl bromides. Yet, in regard to the degree of conversion into various products, chloroalkynes are the most reactive of all the substrates examined under the explored conditions. Optimized conditions for this cross-coupling reaction are presented.

  DOI：

  10.1055/s-0033-1339891
• 作为产物：
  描述：

  4-[(三甲基硅基)乙炔基]苄腈 在 N-氯代丁二酰亚胺 、 四丁基氟化铵 、 silver nitrate 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以97%的产率得到4-(2-氯乙炔基)苯甲腈
  参考文献：
  名称：

  一种多氯联苯和三烷基甲硅烷基保护的炔烃进行1-氯化的高效方法

  摘要：

  报道了1-氯炔和从终端和三烷基甲硅烷保护的前体1-chlorobutadiynes制备A高效单罐方法。这种方便的反应，在温和的条件下继续进行，利用Ñ氯代琥珀酰亚胺作为氯化剂和容忍范围的官能团。

  DOI：

  10.1002/chem.201303680

文献信息

• Synthesis of 1-Chloroalkynes from Alkynylsilanes Using Trichloroisocyanuric Acid as Chlorinating Agent
  作者：Mogens Nielsen、Mie Vilhelmsen、Asbjørn Andersson

  DOI：10.1055/s-0028-1088020

  日期：——

  reported for preparing 1-chloroalkynes from alkynylsilanes using trichloroisocyanuric acid (TCCA) as chlorinating agent and AgNO3 for in situ desilylation. The method is selective for trimethylsilyl-protected alkynes relative to triisopropylsilyl-protected alkynes. alkynes - chlorination - electrophilic additions - imides - protecting groups

  报道了一种新的方法，该方法使用三氯异氰尿酸（TCCA）作为氯化剂，并用AgNO 3原位进行甲硅烷基化反应，由炔基硅烷制备1-氯炔烃。相对于三异丙基甲硅烷基保护的炔，该方法对三甲基甲硅烷基保护的炔是选择性的。 炔烃-氯化-亲电子加成-酰亚胺-保护基
• Preparation of [¹⁸F]Alkenyl Fluorides Using No-Carrier-Added [¹⁸F]AgF via Silver-Mediated Direct Radiofluorination of Alkynes
  作者：Xinyan Gao、Kehao Gong、Mingwei Wang、Bo Xu、Junbin Han

  DOI：10.1021/acs.orglett.2c02553

  日期：2022.9.9

  method for the radiosynthesis of [18F]alkenyl fluorides using no-carrier-added [18F]AgF via the silver-mediated direct radiofluorination of alkynes. A variety of electron-deficient internal alkynes were compatible with this strategy and gave the desired product in good regioselectivity and RCY. This method could also be applied to the late-stage radiofluorination and showed potential in nuclear medicine

  我们开发了一种通用方法，用于通过银介导的炔烃的直接放射性氟化，使用未添加载体的 [ 18 F]AgF 放射性合成 [ 18 F] 烯基氟化物。多种缺电子内部炔烃与该策略兼容，并提供了具有良好区域选择性和 RCY 的所需产物。该方法也可应用于后期放射性氟化，在核医学发展中显示出潜力。
• Silver-Catalyzed Synthesis of 1-Chloroalkynes Directly from Terminal Alkynes
  作者：Dunfa Shi、Zhiwen Liu、Ziyu Zhang、Wei Shi、Hao Chen

  DOI：10.1002/cctc.201500243

  日期：2015.5.4

  AbstractAn efficient method to prepare 1‐chloroalkynes was investigated. The method involved the use of readily available terminal alkynes and a catalytic amount of a silver salt with N‐chlorosuccinimide as the chlorinating agent under mild conditions. Compared with the existing process, this method has a broad substrate scope: 19 examples were explored, and the products were obtained in excellent yields and were easily isolated by vacuum distillation. Moreover, recycling of the catalyst was achieved by simple filtration and desiccation, which made the method more economic and environmentally benign.
• KR101869388
  申请人：——

  公开号：——

  公开（公告）日：——
• Palladium-Catalyzed Cross Haloalkynylation of Haloalkynes
  作者：Xiaoliang Ji、Jinli Nie、Xin Peng、Jinhui Hu、Xuetao Xu、Yubing Huang、Yibiao Li、Huanfeng Jiang

  DOI：10.1021/acs.orglett.2c01161

  日期：2022.5.13