1-[4-(cyclohex-1-enylethynyl)phenyl]-ethanone | 31689-12-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[4-(cyclohex-1-enylethynyl)phenyl]-ethanone
• 英文别名: (cyclohex-1-enyl)(4'-acetylphenyl)acetylene；1-(Cyclohexenylethinyl)-4-acetylbenzol；1-(Cyclohexenylethynyl)-4-(acetyl)benzene；1-[4-[2-(cyclohexen-1-yl)ethynyl]phenyl]ethanone
• CAS: 31689-12-0
• 化学式: C₁₆H₁₆O
• 分子量: 224.302
• InChiKey: OYQBXXPYRMQPHL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-乙炔基环己烷 、 4-碘代苯乙酮 在 aluminum oxide 、 钌 三乙胺 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以60%的产率得到1-[4-(cyclohex-1-enylethynyl)phenyl]-ethanone
  参考文献：
  名称：

  钌/氧化铝用作无铜Sonogashira偶联反应的便捷催化剂

  摘要：

  已经发现，新型的，实用的钌负载在氧化铝上的催化剂体系可以在温和方便的条件下，在各种基材上高效地进行无铜Sonogashira偶联反应。

  DOI：

  10.1002/adsc.200404189

文献信息

• 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。
• Use of Ruthenium/Alumina as a Convenient Catalyst for Copper-Free Sonogashira Coupling Reactions
  作者：Soyoung Park、Min Kim、Dong Hyun Koo、Sukbok Chang

  DOI：10.1002/adsc.200404189

  日期：2004.12

  It has been found that a new and practical catalyst system of ruthenium-supported on alumina carries out copper-free Sonogashira coupling reactions with high efficiency over a wide range of substrates under mild and convenient conditions.

  已经发现，新型的，实用的钌负载在氧化铝上的催化剂体系可以在温和方便的条件下，在各种基材上高效地进行无铜Sonogashira偶联反应。
• Sonogashira Coupling Using Bulky Palladium-Phenanthryl Imidazolium Carbene Catalysis
  作者：Yudao Ma、Chun Song、Wei Jiang、Quansheng Wu、Yong Wang、Xueying Liu、Merritt B. Andrus

  DOI：10.1021/ol035147k

  日期：2003.9.1

  [GRAPHICS]Bulky phenanthracenyl imidazolium-derived carbene ligands were investigated for copper-free Sonogashira coupling with terminal acetylenes. Aryl bromides and iodides gave coupled products in excellent yields from the Pd(PPh3)(2)Cl-2 complex with potassium t-butoxide and 18-crown-6 in THF. A remarkable dependence on the size of the ligand was found. The highest yields were obtained with the bulky 2,9-dicyclohexyl-10-phenanthryl ligand 5.
• US7642391B1
  申请人：——

  公开号：US7642391B1

  公开（公告）日：2010-01-05
• High throughput evaluation of the production of substituted acetylenes by the Sonogashira reaction followed by the Mizoroki–Heck reaction in ionic liquids, in situ, using a novel array reactor
  作者：Md. Taifur Rahman、Takahide Fukuyama、Ilhyong Ryu、Kanae Suzuki、Koichi Yonemura、Philip F. Hughes、Kiyoshi Nokihara

  DOI：10.1016/j.tetlet.2006.02.084

  日期：2006.4

  The parallel Sonogashira coupling reaction was carried out under copper-free condition by integrating the advantages of ionic liquids as the reaction media followed by the simultaneous-multiple Mizoroki-Heck reaction in Situ by the use of a novel array reactor (SynArray-24). The device provides rapid evaluation of reactions in a short period. (c) 2006 Elsevier Ltd. All rights reserved.