(cyclohex-1-enyl)(2'-methylphenyl)acetylene

• 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: (cyclohex-1-enyl)(2'-methylphenyl)acetylene
• 英文别名: 1-(cyclohex-1-enylethynyl)-2-methylbenzene；1-[2-(Cyclohexen-1-yl)ethynyl]-2-methylbenzene
• 化学式: C₁₅H₁₆
• 分子量: 196.292
• InChiKey: LUWLJIGINWJBRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  1-乙炔基环己烷 、 2-碘代甲苯 在 palladium diacetate 四丁基醋酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以96%的产率得到(cyclohex-1-enyl)(2'-methylphenyl)acetylene
  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

• Direct Synthesis of Alkynylstannanes: ZnBr₂Catalyst for the Reaction of Tributyltin Methoxide and Terminal Alkynes
  作者：Kensuke Kiyokawa、Nodoka Tachikake、Makoto Yasuda、Akio Baba

  DOI：10.1002/anie.201104208

  日期：2011.10.24

  Metal hopping: Various alkynylstannanes were synthesized by the direct reaction of Bu3SnOMe with terminal alkynes at room temperature in the presence of a ZnBr2 catalyst. Rather than acting as a Lewis acid, ZnBr2 was transmetalated with Bu3SnOMe to give Zn(OMe)2, which is key to the catalytic reaction.

  金属跳跃：通过在室温下在ZnBr 2催化剂存在下，Bu 3 SnOMe与末端炔烃直接反应，合成了各种炔基锡烷。ZnBr 2不是用作路易斯酸，而是用Bu 3 SnOMe进行金属转移生成Zn（OMe）2，这对催化反应至关重要。
• 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.
• 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。