2-cyclohexylnaphthalene | 42044-07-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-cyclohexylnaphthalene
• CAS: 42044-07-5
• 化学式: C₁₆H₁₈
• 分子量: 210.319
• InChiKey: LFOAKQQHKCCFNY-UHFFFAOYSA-N

物化性质

• 熔点：
  31 °C
• 沸点：
  150-152 °C(Press: 0.65 Torr)
• 密度：
  1.0074 g/cm3(Temp: 40 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-cyclohexylnaphthalene 在 sulfur 作用下， 生成 2-苯基萘
  参考文献：
  名称：

  茚满和四氢萘被烯烃，醇和二乙醚催化烷基化。

  摘要：

  DOI：

  10.1021/ja01192a017
• 作为产物：
  描述：

  八氢-并环戊二烯 在 mercury (II) chloride 作用下， 生成 2-cyclohexylnaphthalene
  参考文献：
  名称：

  Synthesis, spectral and structural characterization of Ni(II), Cu(II), Zn(II), Cd(II) and Hg(II) complexes with 2-mercapto-5-methyl-1,3,4-thiadiazole: A Zn(II) complex acting as a new sensitive and selective fluorescent probe for the detection of Hg2+ in H2O–MeOH medium

  摘要：

  Five new complexes, [Ni(mthd)(2)(py)(2)] (1), [Cu(en)(2)](mthd)(2) (2), [H(2)en][Hg(mthd)(3)](2)center dot 2H(2)O (3), [Cd(mthd)(2)(o-phen)(2)](2)center dot H2O (4) and [Zn(mthd)(2)(bpy)] (5) (Hmthd = 2-mercapto-5-methyl-1,3,4-thiadiazole), have been synthesized. All the complexes have been fully characterized by various techniques: elemental analyses, IR, electronic and fluorescent spectral data. The ligand is present in the deprotonated thiol form in the complexes [Cu(en)(2)](mthd)(2) (2) and [Cd(mthd)(2)(o-phen)(2)]2 center dot H2O (4). In complex 2, the ligand is ionically bonded, whereas it is covalently bonded through the sulfur in complex 4. In [Ni(mthd)(2)(py)(2)] (1) the ligand is N,S chelating bidentate bonded through the thiol sulfur and the thiadiazole ring nitrogen adjacent to it, forming a four membered chelate ring. The ligand is covalently bonded through the deprotonated thiadiazole ring nitrogen adjacent to the thiol sulfur in [Zn(mthd)(2)(bpy)] (5). The complex anion in [H(2)en][Hg(mthd)(3)](2)center dot 2H(2)O (3) has a triangular planar geometry, with bonding through the deprotonated thiolato sulfur atoms from the three ligands. [Zn(mthd)(2)(bpy)] (5) is highly fluorescent as compared to the other complexes and has been further used as a metal probe for sensing of Hg2+ in H2O-MeOH solution. Complex 5, upon interaction with Hg2+, shows a hypochromic shift in the absorption spectra whereas the emission spectra exhibited 75% quenching fluorescence behavior. The electrochemical studies also suggest the interaction of Hg(II) with the Zn(II) complex, probably via the free thione sulfur. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2013.07.027

文献信息

• Iron-Catalyzed Cross-Coupling of Primary and Secondary Alkyl Halides with Aryl Grignard Reagents
  作者：Masaharu Nakamura、Keiko Matsuo、Shingo Ito、Eiichi Nakamura

  DOI：10.1021/ja049744t

  日期：2004.3.1

  An iron-catalyzed cross-coupling reaction of a primary or secondary alkyl halide with an aryl Grignard reagent proceeds under mild conditions to give the corresponding coupling product in quantitative yield.

  伯或仲烷基卤化物与芳基格氏试剂的铁催化交叉偶联反应在温和条件下进行，以定量产率得到相应的偶联产物。
• A New Class of Stable, Saturated N‐Heterocyclic Carbenes with <i>N</i> ‐Naphthyl Substituents: Synthesis, Dynamic Behavior, and Catalytic Potential
  作者：Ludovic Vieille‐Petit、Xinjun Luan、Ronaldo Mariz、Sascha Blumentritt、Anthony Linden、Reto Dorta

  DOI：10.1002/ejic.200900010

  日期：2009.5

  comprised of substituted naphthyl units. This generates C2-symmetric (anti) and Cs-symmetric (syn) atropisomers. The interconversion between the isomers is studied in detail both for the N-heterocyclic carbene salts and the free carbenes through variable-temperature 1H NMR spectroscopic studies; activation free energies are calculated and can be linked to the substitution pattern of the naphthyl moieties

  已经合成了一个新的易于获得且稳定的咪唑啉-2-亚基，其中侧链由取代的萘基单元组成。这会生成 C2 对称（反）和 Cs 对称（syn）阻转异构体。通过变温 1H NMR 光谱研究，详细研究了 N-杂环卡宾盐和游离卡宾的异构体之间的相互转化；计算活化自由能并且可以将其与萘基部分的取代模式相关联。合成了包含新 N-杂环卡宾的钯配合物，初步数据表明这些化合物在芳基溴和芳基氯的 Buchwald-Hartwig 胺化反应中作为预催化剂表现良好。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
• A New Convenient Friedel-Crafts Alkylation of Aromatic Compounds with Secondary Alcohol Methanesulfonates in the Presence of Scandium(III)Trifluoromethanesulfonate or Trifluoromethanesulfonic Acid as the Catalyst
  作者：Hiyoshizo Kotsuki、Takeshi Ohishi、Motoshi Inoue、Tomoyuki Kojima

  DOI：10.1055/s-1999-3436

  日期：1999.4

  Scandium(III) triflate and triflic acid were both found to be efficient catalysts for the Friedel-Crafts alkylation of aromatic compounds using methanesulfonates derived from secondary alcohols as alkylating agents.

  铈（III）三氟甲基磺酸盐和三氟甲基磺酸均被发现是芳香化合物的 Friedel-Crafts 炭链化反应的有效催化剂，使用来自二级醇的甲基磺酸盐作为烷基化试剂。
• Scandium(III) Trifluoromethanesulfonate-Catalyzed Friedel-Crafts Alkylation of Aromatic Compounds with Secondary Alcohol Methanesulfonates
  作者：Hiyoshizo Kotsuki、Takeshi Oshisi、Motoshi Inoue

  DOI：10.1055/s-1998-1649

  日期：1998.3

  Scandium(III) triflate was found to be an efficient catalyst for the Friedel-Crafts alkylation of aromatic compounds with methanesulfonates derived from secondary alcohols; the catalyst can be reused without a significant loss of activity.

  三氟甲磺酸钪被发现是芳香化合物与衍生自 secondary alcohols 的甲磺酸盐进行 Friedel-Crafts 烷基化反应的高效催化剂；该催化剂可以重复使用而活性损失甚微。
• Nickel-Catalyzed Alkylative Cross-Coupling of Anisoles with Grignard Reagents via C–O Bond Activation
  作者：Mamoru Tobisu、Tsuyoshi Takahira、Toshifumi Morioka、Naoto Chatani

  DOI：10.1021/jacs.6b03253

  日期：2016.6.1

  We report nickel-catalyzed cross-coupling of methoxyarenes with alkylmagnesium halides, in which a methoxy group is eliminated. A wide range of alkyl groups, including those bearing β-hydrogens, can be introduced directly at the ipso position of anisole derivatives. We demonstrate that the robustness of a methoxy group allows this alkylation protocol to be used to synthesize elaborate molecules by

  我们报告了镍催化的甲氧基芳烃与烷基卤化镁的交叉偶联，其中甲氧基被消除。广泛的烷基，包括那些带有 β-氢的烷基，可以直接在苯甲醚衍生物的 ipso 位置引入。我们证明甲氧基的稳健性允许该烷基化方案通过将其与传统的交叉偶联反应或氧化转化相结合来合成复杂的分子。这种方法的成功取决于使用烷基碘化镁，而不是氯化物或溴化物，这突出了卤化物在使用格氏试剂进行催化反应中的重要性。