1-((Z)-4-p-tolylbut-1-en-3-ynyl)benzene | 1385634-93-4

• 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: 1-((Z)-4-p-tolylbut-1-en-3-ynyl)benzene
• 英文别名: (Z)-1-phenyl-4-tolylbut-1-en-3-yne
• CAS: 1385634-93-4
• 化学式: C₁₇H₁₄
• 分子量: 218.298
• InChiKey: NPHJKRBZEWRGLP-UITAMQMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  17.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  1-(2-溴乙炔基)-4-甲基苯 、 4,4,5,5-tetramethyl-2-[(1Z)-2-phenylethenyl]-1,3,2-dioxaborolane 在 copper(II) ferrite 、 caesium carbonate 作用下， 反应 12.0h， 以74%的产率得到1-((Z)-4-p-tolylbut-1-en-3-ynyl)benzene
  参考文献：
  名称：

  Cu-Catalyzed Fe-Driven C_sp–C_sp and C_sp–C_sp2 Cross-Coupling: An Access to 1,3-Diynes and 1,3-Enynes

  摘要：

  An efficient Csp-Csp cross-coupling of alkynyl bromide and pinacol ester of alkynyl boronic acid catalyzed by CuFe2O4 nanoparticles has been accomplished in dimethyl carbonate to produce unsymmetric 1,3-diynes. This protocol is also extended for the Csp-Csp2 coupling of alkynyl bromide and alkenyl boronic acid to provide conjugated 1,3-enynes. The aliphatic, aromatic, and heteroaromatic alkynes couple with various substituted alkynyl/alkenyl boronates/boronic acids by this procedure to furnish a library of 1,3-diynes and enynes in high yields. The catalyst was easily separated by an external magnet and recycled 10 times.

  DOI：

  10.1021/jo5011069

文献信息

• Discovery of A Novel Palladium Catalyst for the Preparation of Enynes with a Copper- and Ligand-Free Sonogashira Reaction
  作者：Mengmeng Huang、Yangjie Wu、Xia Mi、Yujian Feng

  DOI：10.1055/s-0031-1290938

  日期：2012.5

  catalytic systems are tolerant in the presence of a broad variety of functional groups in the substrates. The catalytic system was found to be ineffective for vinyl chloride. Moreover, it was found that (Z)-β-bromostyrene reacts with terminal alkynes with retention of the steric configuration and the transformation of most of the Z-isomer did not occur in this reaction.

  基于 N,N-二甲基乙醇胺 (SP-4-1')-双 [N,N-二甲基氨基乙氧基-kN,O] 钯 (II) 的新型钯 (II) 配合物与两摩尔的 AcOH 配位，已被合成的。通过 X 射线衍射分析确定了配合物的结构。使用这种配合物作为催化剂，在没有助催化剂 CuX 和任何配体的情况下，在室温下 20 小时内，通过 Sonogashira 交叉偶联反应成功合成了一系列共轭烯炔，以中等至优异的产率得到相应的产物。优化的催化系统可以耐受底物中存在多种官能团。发现该催化体系对氯乙烯无效。而且，
• A polystyrene supported [PdCl–(SeCSe)] complex: a novel, reusable and robust heterogeneous catalyst for the Sonogashira synthesis of 1,2-disubstituted alkynes and 1,3-enynes
  作者：Elmira Mohammadi、Barahman Movassagh

  DOI：10.1039/c8nj01042k

  日期：——

  g−1). The PS[PdCl–SeCSe] catalytic activity has been evaluated in the Sonogashira coupling of diverse aryl halides with aromatic and aliphatic terminal alkynes. It was also noted that less reactive and inexpensive aryl bromides and aryl chlorides have been successfully cross-coupled with terminal alkynes using low catalyst loading. Moreover, the developed methodology is effective for the stereoselective

  3,5-双（（苯基硒基甲基）甲基）苯酚已通过多步合成从市售的5-羟基间苯二甲酸合成为新型SECSE夹钳型预配体。然后，使用包括FT-IR，SEM / EDX，TG / DTG和XPS在内的不同技术，制备并表征了聚苯乙烯负载的SECSE钳形配体及其相应的钯配合物。通过ICP分析确定的掺入聚合物基质中的钯的量为3.64wt％（0.34mmol g -1））。在各种芳基卤化物与芳族和脂族末端炔烃的Sonogashira偶联中，已评估了PS [PdCl–SECSE]的催化活性。还应注意的是，使用低催化剂负载量，已成功地将反应性较低且价格便宜的芳基溴化物和芳基氯化物与末端炔烃进行了交叉偶联。而且，开发的方法对于取代的1，3-烯炔的立体选择性制备是有效的。