1-(cyclohexylethynyl)naphthalene | 1445859-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(cyclohexylethynyl)naphthalene
• 英文别名: 1-(2-Cyclohexylethynyl)naphthalene
• CAS: 1445859-03-9
• 化学式: C₁₈H₁₈
• 分子量: 234.341
• InChiKey: IWMMMLUVBWMECS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• 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

• 作为反应物：
  描述：

  1-(cyclohexylethynyl)naphthalene 在 水 、 silver trifluoromethanesulfonate 作用下， 以 氯苯 为溶剂， 以71 %的产率得到2-cyclohexyl-1-(naphthalen-1-yl)ethan-1-one
  参考文献：
  名称：

  Accurate Control on the Nucleophilic Addition of H2O to Internal Alkynes: An Ag catalyzed Regiospecific Hydration Strategy

  摘要：

  In the absence of directing auxiliaries, catalytic addition of nucleophiles to unactivated alkynes with accurate control of regioselectivity remains an ongoing challenge in organic chemistry. Herein, we realized a Ag‐catalysed regiospecific hydration process of unactivated alkynes. Computational investigations offered insights into the origin of the regiochemical outcome. The practicability and efficacy of the protocol was exemplified by its simple reaction conditions without incorporation of acidic additives, as well as the toler‐ance of a wide range of alkynes equipped with various functional groups, leading to the ketone products in up to 98% yield. Direct modification of bioactive organic molecules and gram‐scale experiments further showcased the application potential of the strategy. The catalyst control principles are expected to advance efforts towards the development of general site‐selective addition of nucleophile to unsaturated substrates, removing the requirement for neighboring activating groups.

  DOI：

  10.1002/cctc.202400735
• 作为产物：
  描述：

  1-乙炔基萘 在 4-氰基吡啶 、 叔丁基过氧化氢 、 4-氰基吡啶 N-氧化物 、 碘 、 联硼酸新戊二醇酯 作用下， 以 四氢呋喃 为溶剂， 反应 28.0h， 生成 1-(cyclohexylethynyl)naphthalene
  参考文献：
  名称：

  硼烷自由基介导的灭活烷烃的CH活化，用于内部炔烃的合成

  摘要：

  描述了一个有趣的吡啶-硼基自由基介导的灭活烷烃的CH炔基化反应。该反应具有温和的操作条件和广泛的底物范围，并以中等至良好的产率提供了相应的产物。值得注意的是，4-氰基吡啶N-氧化物的存在是反应成功的关键。环己烷比甲苯更容易在该反应中被官能化，这可以用极性匹配原理合理地解释。

  DOI：

  10.1002/adsc.202000772

文献信息

• Visible light promoted coupling of alkynyl bromides and Hantzsch esters for the synthesis of internal alkynes
  作者：Zhi-Yong Song、Chun-Lin Zhang、Song Ye

  DOI：10.1039/c8ob02912a

  日期：——

  A metal-free visible light promoted C(sp3)–C(sp) coupling reaction of alkynyl bromides and Hantzsch esters was developed, giving internal alkynes with primary, secondary, tertiary alkyl or other functional groups in good to high yields.

  开发了一种无金属的可见光促进炔基溴化物和Hantzsch酯的C（sp 3）–C（sp）偶联反应，从而使内部炔烃具有伯，仲，叔烷基或其他官能团，并具有良好或高收率。
• Microwave-Promoted Copper-Free Sonogashira-Hagihara Couplings of Aryl Imidazolylsulfonates in Water
  作者：José F. Cívicos、Diego A. Alonso、Carmen Nájera

  DOI：10.1002/adsc.201200629

  日期：2013.1.14

  Aryl imidazol‐1‐ylsulfonates have been efficiently cross‐coupled with aryl‐, alkyl‐, and silylacetylenes in neat water under copper‐free conditions at 110 °C assisted by microwave irradiation. Using 0.5 mol% of an oxime palladacycle as precatalyst, 2‐dicyclohexylphosphino‐2′,6′‐dimethoxybiphenyl (SPhos, 2 mol%) as ligand, hexadecyltrimethylammonium bromide (CTAB) as additive, and triethylamine (TEA)

  在110℃无铜条件下，微波辐射辅助下，纯净水中的芳基咪唑-1-基磺酸盐已与芳基，烷基和甲硅烷基乙炔有效地交叉偶联。使用0.5摩尔％的肟四氮杂环丙烷作为前催化剂，使用2-二环己基膦基2'，6'-二甲氧基联苯（SPhos，2摩尔％）作为配体，十六烷基三甲基溴化铵（CTAB）作为添加剂，并使用三乙胺（TEA）作为碱仅30分钟就可以制备出高至高收率的双取代炔烃阵列。
• Stoichiometric and Catalytic Lithium Nickelate-Mediated C–F Bond Alkynylation of Fluoroarenes
  作者：Andryj M. Borys、Luca Vedani、Eva Hevia

  DOI：10.1021/jacs.4c02606

  日期：2024.4.10

  cross-coupling reactions under mild conditions. Expanding the synthetic potential of these heterobimetallic complexes, herein we report the success of trilithium nickelate Li3(TMEDA)3Ni(C≡C–Ph)3 in promoting stoichiometric C–F activation of assorted aryl fluorides furnishing novel mixed Li/Ni(0) or Li/Ni(II) species depending on the substrate and conditions employed. These stoichiometric successes can

  低价镍酸盐最近被证明是在温和条件下促进具有挑战性的交叉偶联反应的关键中间体。为了扩大这些异双金属配合物的合成潜力，本文报道了镍酸三锂 Li 3 (TMEDA) 3 Ni(C≡C–Ph) 3成功促进了各种芳基氟化物的化学计量 C–F 活化，从而提供了新型混合 Li/Ni( 0) 或 Li/Ni(II) 物质，具体取决于所用的基材和条件。这些化学计量的成功可以升级到催化方案，以实现芳基氟化物和多氟芳烃与乙炔锂和预催化剂 Ni(COD) 2的原子效率炔基化，无需外部配体、Cu 助催化剂或添加剂的干预。