4-(6-hydroxyhex-1-yn-1-yl)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-(6-hydroxyhex-1-yn-1-yl)benzonitrile
• 英文别名: 4-(6-hydroxy-hex-1-ynyl)-cyanobenzene；4-(6-hydroxyhex-1-ynyl)benzonitrile
• 化学式: C₁₃H₁₃NO
• 分子量: 199.252
• InChiKey: PVOPEEVBGYOFBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  44
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(6-hydroxyhex-1-yn-1-yl)benzonitrile 在 三氧化硫吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 以77%的产率得到4-(6-oxohex-1-yn-1-yl)benzonitrile
  参考文献：
  名称：

  串联金属环形成/交叉电化学偶联合成四取代烯烃

  摘要：

  镍催化的交叉亲电偶联最近已成为形成 CC 键的高效实用方法。通过将此过程与成熟的 π-π 偶联化学相结合，开发了一种合成四取代烯烃的新方法。该过程依赖于使用氯硅烷作为产生反应性乙烯基镍中间体的手段，这些中间体能够与卤代烷进行还原性交叉亲电偶联。该方法不仅可以生成高度取代的烯丙醇衍生物，而且不需要化学计量的有机金属亲核试剂，与以前开发的方法相比，范围和官能团耐受性大大提高。

  DOI：

  10.1021/jacs.8b04637
• 作为产物：
  描述：

  5-己炔-1-醇 、 4-溴苯腈 在 tris(dibenzylideneacetone)dipalladium (0) 四丁基醋酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以94%的产率得到4-(6-hydroxyhex-1-yn-1-yl)benzonitrile
  参考文献：
  名称：

  芳基碘化物和溴化物与末端炔烃的无配体，无铜和无胺Sonogashira反应

  摘要：

  已经开发出有效的无配体，无铜和无胺的钯催化的芳基碘化物和溴化物与末端炔烃的Sonogashira反应的条件。该新方案成功的关键是使用乙酸四丁铵作为碱。该方法的显着特征是室温条件和两个反应伙伴中多种官能团的耐受性。

  DOI：

  10.1021/jo049325e

文献信息

• Coupling reactions of aryl bromides with 1-alkynols catalysed by a tetraphosphine/palladium catalyst
  作者：Marie Feuerstein、Henri Doucet、Maurice Santelli

  DOI：10.1016/j.tetlet.2003.12.128

  日期：2004.2

  cis. cis, cis-1, 2, 3,4-Tetrakis(diphenylphosphinomethyl)cyclopentane/[PdCl(C3H5)](2) system catalyses efficiently the coupling reactions of aryl halides with a variety of alkynols such as propargy] alcohol, but-1-yn-4-ol, pent-1-yn-5-ol or hex-1-yn-6-ol. The catalyst can be used at lowloading. Higher reaction rates were observed in the presence of but-1-yn-4-ol, pent-1-yn-5-ol or hex-1-yn-6-ol than with propargy] alcohol. The protection of the alcohol functions as an ether or a silyloxy group led generally to similar or better results than the reactions performed with the unprotected alcohols. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.
• Ligand-, Copper-, and Amine-Free Sonogashira Reaction of Aryl Iodides and Bromides with Terminal Alkynes
  作者：Sameer Urgaonkar、John G. Verkade

  DOI：10.1021/jo049325e

  日期：2004.8.1

  and amine-free palladium-catalyzed Sonogashira reaction of aryl iodides and bromides with terminal alkynes have been developed. Critical to the success of this new protocol is the use of tetrabutylammonium acetate as the base. Noteworthy features of this method are room-temperature conditions and the tolerance of a broad range of functional groups in both reaction partners.

  已经开发出有效的无配体，无铜和无胺的钯催化的芳基碘化物和溴化物与末端炔烃的Sonogashira反应的条件。该新方案成功的关键是使用乙酸四丁铵作为碱。该方法的显着特征是室温条件和两个反应伙伴中多种官能团的耐受性。
• Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling
  作者：Kirk W. Shimkin、John Montgomery

  DOI：10.1021/jacs.8b04637

  日期：2018.6.13

  Nickel-catalyzed cross-electrophile couplings have recently emerged as highly effective and practical methods for the formation of C-C bonds. By merging this process with well-established π-π coupling chemistry, a new method for the synthesis of tetrasubstituted alkenes has been developed. The procedure relies on the use of chlorosilanes as a means of generating reactive vinylnickel intermediates,

  镍催化的交叉亲电偶联最近已成为形成 CC 键的高效实用方法。通过将此过程与成熟的 π-π 偶联化学相结合，开发了一种合成四取代烯烃的新方法。该过程依赖于使用氯硅烷作为产生反应性乙烯基镍中间体的手段，这些中间体能够与卤代烷进行还原性交叉亲电偶联。该方法不仅可以生成高度取代的烯丙醇衍生物，而且不需要化学计量的有机金属亲核试剂，与以前开发的方法相比，范围和官能团耐受性大大提高。