4-(cyclohex-1-enylethynyl)benzonitrile

• 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: 4-(cyclohex-1-enylethynyl)benzonitrile
• 英文别名: 4-(Cyclohexenylethynyl)benzonitrile；4-(Cyclohex-1-en-1-ylethynyl)benzonitrile；4-[2-(cyclohexen-1-yl)ethynyl]benzonitrile
• 化学式: C₁₅H₁₃N
• 分子量: 207.275
• InChiKey: DBCTUUVKJQHZJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  对氯苯甲腈 、 1-乙炔基环己烷 在 双(乙腈)氯化钯(II) 、 caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以93%的产率得到4-(cyclohex-1-enylethynyl)benzonitrile
  参考文献：
  名称：

  芳基氯和甲苯磺酸酯与末端炔烃的钯催化高效偶联：使用铜助催化剂可抑制反应。

  摘要：

  DOI：

  10.1002/anie.200353015

文献信息

• Palladium-Catalyzed Sonogashira Coupling of Aryl Mesylates and Tosylates
  作者：Pui Ying Choy、Wing Kin Chow、Chau Ming So、Chak Po Lau、Fuk Yee Kwong

  DOI：10.1002/chem.201001269

  日期：2010.9.3

  Up to speed: The first general and mild protocol for the Sonogashira coupling of aryl mesylates is presented (see scheme). The coupling intermediate also provides facile access to 2‐substituted isoquinolines.

  加快速度：提出了甲磺酸甲磺酸酯的Sonogashira偶联的第一个一般性和温和的方案（请参阅方案）。偶联中间体还提供了2取代异喹啉的便捷通道。
• Efficient Palladium-Catalyzed Coupling of Aryl Chlorides and Tosylates with Terminal Alkynes: Use of a Copper Cocatalyst Inhibits the Reaction
  作者：Dmitri Gelman、Stephen L. Buchwald

  DOI：10.1002/anie.200353015

  日期：2003.12.15
• Sonogashira cross-coupling reactions of aryl chlorides with alkynes catalysed by a tetraphosphine–palladium catalyst
  作者：Marie Feuerstein、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tetlet.2004.09.092

  日期：2004.11

  A range of aryl chlorides undergoes cross-couplings with alkynes in good yields in the presence of [PdCl(C3H5)](2)/cis,cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl)cyclopentane as catalyst. A variety of aryl chlorides such as chloroacetophenone, chlorobenzonitrile, chloronitrobenzene, chloroanisole or chlorotoluene have been used successfully. The reaction also tolerates several alkynes such as phenylacetylene, dec-l-yne, ethynylcyclohexene or alk-l-ynols. Furthermore, this catalyst can be used at low loading with some substrates. (C) 2004 Elsevier Ltd. All rights reserved.
• Heck Alkynylation (Copper-Free Sonogashira Coupling) of Aryl and Heteroaryl Chlorides, Using Pd Complexes of <i>t</i>-Bu₂(<i>p</i>-NMe₂C₆H₄)P: Understanding the Structure–Activity Relationships and Copper Effects
  作者：Xiaotao Pu、Hongbo Li、Thomas J. Colacot

  DOI：10.1021/jo302195y

  日期：2013.1.18

  L2Pd(0) and L2Pd(II) complexes, where L=t-Bu-2(p-NMe2C6H4)P, have been identified as efficient catalyst systems for the Heck alkynylation of a variety of aryl bromides (17 examples) and aryl/heteroaryl chlorides (31 examples) with a range of aryl- and alkyl-acetylenes in excellent yields, under relatively low Pd loadings. The single-crystal X-ray structure determination of the presumably active catalytic species, L2Pd(0), was carried out in this study to better understand the superior activity of the current catalyst system from a structure activity relationship point of view. The P-Pd-P bond angle indicates that the complex is bent (174.7 degrees) in comparison to the perfectly linear (180.0 degrees) structure of the analogous Pd(t-Bu3P)(2). Preliminary mechanistic studies on the negative copper effect and substrate effect of aryl acetylenes were conducted to better understand the cross-coupling pathway of Heck alkynylation.