1-(cyclohexyloxy)naphthalene | 21571-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-(cyclohexyloxy)naphthalene
• 英文别名: 1-naphthyl cyclohexyl ether；1-cyclohexyloxynaphthalene
• CAS: 21571-62-0
• 化学式: C₁₆H₁₈O
• mdl: MFCD21435378
• 分子量: 226.318
• InChiKey: FVYLLEKHRHXQKV-UHFFFAOYSA-N

物化性质

• 沸点：
  362.8±11.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.375
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-溴代萘 、 环己醇 在 tris(dibenzylideneacetone)dipalladium (0) 、 (±)-2,2 '-二(二-对甲苯基膦)-1,1 '-联萘 sodium hydride 作用下， 以 甲苯 为溶剂， 以65%的产率得到1-(cyclohexyloxy)naphthalene
  参考文献：
  名称：

  Palladium-Catalyzed Intermolecular Carbon−Oxygen Bond Formation:  A New Synthesis of Aryl Ethers

  摘要：

  DOI：

  10.1021/ja9640152

文献信息

• Heterogeneous Palladium-Catalyzed Synthesis of Aromatic Ethers by Solvent-Free Dehydrogenative Aromatization: Mechanism, Scope, and Limitations Under Aerobic and Non-Aerobic Conditions
  作者：Marc Sutter、Romain Lafon、Yann Raoul、Estelle Métay、Marc Lemaire

  DOI：10.1002/ejoc.201300485

  日期：2013.9

  derivatives and alcohols, both non-aromatic precursors, aryl ethers could be synthesized in good yields and with good selectivities in the presence of a catalytic amount of Pd/C, in one step, without added solvent, in a reaction vessel open to air. For less reactive substrates, the addition of 1-octene in a closed system under non-aerobic conditions improved the conversion. In addition, the catalyst could

  以环己酮衍生物和醇为原料，这两种非芳香族前体，芳醚可以在催化量的 Pd/C 存在下以良好的产率和良好的选择性在一个步骤中合成，无需添加溶剂，在打开的反应容器中空气。对于反应性较低的底物，在非有氧条件下在封闭系统中添加 1-辛烯可提高转化率。此外，催化剂可以循环多次使用，芳醚收率没有下降。该方法也用于四氢萘酮衍生物和多元醇。进行了几个反应以提出这种转化的机制。形成烯醇醚，然后进行脱氢反应似乎是该反应的关键步骤。
• Copper Catalyzed sp³ C–H Etherification with Acyl Protected Phenols
  作者：Tolani K. Salvador、Charles H. Arnett、Subrata Kundu、Nicholas G. Sapiezynski、Jeffery A. Bertke、Mahdi Raghibi Boroujeni、Timothy H. Warren

  DOI：10.1021/jacs.6b09057

  日期：2016.12.28

  A variety of acyl protected phenols AcOAr participate in sp3 C-H etherification of substrates R-H to give alkyl aryl ethers R-OAr employing tBuOOtBu as oxidant with copper(I) β-diketiminato catalysts [CuI]. Although 1°, 2°, and 3° C-H bonds may be functionalized, selectivity studies reveal a preference for the construction of hindered, 3° C-OAr bonds. Mechanistic studies indicate that β-diketiminato

  多种酰基保护的酚 AcOAr 参与底物 RH 的 sp3 CH 醚化，以 tBuOOtBu 作为氧化剂与铜 (I) β-二酮亚胺催化剂 [CuI] 一起得到烷基芳基醚 R-OAr。尽管 1°、2° 和 3° CH 键可以被官能化，但选择性研究表明优先构建受阻的 3° C-OAr 键。机理研究表明，β-二酮亚氨基铜 (II) 酚盐 [CuII]-OAr 在此 CO 键形成反应中起关键作用，通过 AcOAr 与 [CuI]-OtBu 中间体的酯交换反应形成 [CuI] 与 tBuOOtBu 反应。
• Metal ions and complexes in organic reactions. Part IX. Copper(I)-catalysed conversion of aryl halides into alkyl aryl ethers
  作者：R. G. R. Bacon、S. C. Rennison

  DOI：10.1039/j39690000312

  日期：——

  heterogeneous catalytic conditions, e.g., in solutions containing a suspension of copper(I) oxide, reaction could in some cases be diverted to nucleophilic sustitution (ArHal → ArOAlk) by operating with a substantially homogeneous liquid medium containing copper(I) salts as catalysts. In a suitably chosen reaction system, e.g., ArHal–NaOAlk–AlkOH–Cul–2,4,6-collidine, at ∼100–120°, high yields of ethers resulted

  而醇钠还原芳基卤化物（ArHal →多相催化条件下，ARH）例如，在含有悬浮液的铜溶液（我），氧化反应可以在某些情况下被转移到亲核sustitution（ArHal →由具有基本上操作ArOAlk）含有铜（I）盐作为催化剂的均质液体介质。在适当选择的反应系统中，例如，ArHal–NaOAlk–AlkOH–Cul–2,4,6-可力丁在约100–120°的温度下，从正常的一元链烷醇衍生而来的醇盐导致醚的高收率，但还原反应通常以其他类型醇中的醇盐为主。由单环或多环芳基溴化物或碘化物，包括含有Me，OMe或CO 2 H基团作为核取代基的甲基或乙基醚（约80–100％）制备，可以举例说明这一过程。当OH或NH 2为取代基时，收率较低（约35–50％），这可能是由于它们参与竞争反应，而当NO 2，CHO或COMe为取代基时则未获得醚。
• Synthesis of aryl ethers
  申请人：——

  公开号：US20010008942A1

  公开（公告）日：2001-07-19

  A method for preparing an aryl ether compound is provided in which an alcohol is reacted with an aromatic compound in the presence of a base, and a transition metal catalyst selected from the group consisting of platinum and nickel to form an aryl ether. The aromatic compound comprises an activated substituent, X, said activated substituent being a moiety such that its conjugate acid HX has a pKa of less than 5.0. The catalyst is preferably a soluble palladium complex in the presence of supporting ligands.

  提供了一种制备芳基醚化合物的方法，其中在碱的存在下，醇与芳香化合物反应，并选择铂和镍等过渡金属催化剂形成芳基醚。芳香化合物包括活化取代基X，所述活化取代基是一种它的共轭酸HX具有小于5.0的pKa的基团。催化剂最好是存在支持配体的可溶性钯络合物。
• Organic electroluminescence device
  申请人：IDEMITSU KOSAN COMPANY LIMITED

  公开号：EP0569827A2

  公开（公告）日：1993-11-18

  Disclosed is an organic electroluminescence device which comprises laminating layers in the order of anode/light emitting layer/adhesive layer/cathode, or anode/hole-injecting layer/light emitting layer/adhesive layer/cathode, the energy gap of the light emitting layer being larger than that of 8-hydroxyquinoline or metal complex thereof and contained in the adhesive layer, the light emitting layer comprising a compound which emits a blue, greenish blue or bluish green light in CIE chromaticity coordinates, and the adhesive layer including a metal complex of 8-hydroxyquinoline or a derivative thereof and at least one organic compound in an arbitrary region in the direction of the thickness of the layer, the thickness of which is smaller than that of the above-mentioned light emitting layer. According to the above organic electroluminescence device, improvements in uniformity in light emission and emission efficiency are realized.

  本发明公开了一种有机电致发光器件，该器件包括按阳极/发光层/粘合剂层/阴极或阳极/注孔层/发光层/粘合剂层/阴极的顺序层叠的层，发光层的能隙大于8-羟基喹啉或其金属络合物的能隙并包含在粘合剂层中、发光层包括在CIE色度坐标中发出蓝光、蓝绿色光或蓝绿色光的化合物，粘合层包括8-羟基喹啉或其衍生物的金属络合物和至少一种有机化合物，粘合层的厚度小于上述发光层的厚度。 根据上述有机电致发光装置，实现了光发射均匀性和发射效率的改善。