(1-萘基)(2-萘基)甲烷 | 611-48-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (1-萘基)(2-萘基)甲烷
• 英文名称: 1,2'-Dinaphthylmethan
• 英文别名: 1,2'-Dinaphthylmethane；1-(naphthalen-2-ylmethyl)naphthalene
• CAS: 611-48-3
• 化学式: C₂₁H₁₆
• 分子量: 268.358
• InChiKey: GPCYJQRKJVLCBS-UHFFFAOYSA-N

物化性质

• 熔点：
  89-91 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  452.0±15.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 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-萘基(2-萘基)甲醇 在 氢碘酸 、 溶剂黄146 作用下， 生成 (1-萘基)(2-萘基)甲烷
  参考文献：
  名称：

  Tschitschibabin, Chemische Berichte, 1911, vol. 44, p. 442

  摘要：

  DOI：

文献信息

• Insights into the Role of New Palladium Pincer Complexes as Robust and Recyclable Precatalysts for Suzuki-Miyaura Couplings in Neat Water
  作者：Blanca Inés、Raul SanMartin、María Jesús Moure、Esther Domínguez

  DOI：10.1002/adsc.200900345

  日期：2009.9

  Suzuki–Miyaura biaryl and diarylmethane syntheses via the coupling of arylboronic acids with aryl and arylmethyl bromides are performed in water by means of two new CNC-type palladium pincer complexes. Good to excellent results (including high TON values and extended recycling procedures) are obtained in most cases for a range of electronically dissimilar halides and boronic acids. On the basis of

  水中的铃木-宫浦联芳基和二芳基甲烷通过芳基硼酸与芳基和芳基甲基溴的偶联而合成，是通过两种新型的CNC型钯钳配合物在水中进行的。在大多数情况下，对于一系列电子不同的卤化物和硼酸，可获得良好至优异的结果（包括较高的TON值和扩展的回收程序）。在一系列动力学研究，透射电子显微镜（TEM），汞滴试验和定量中毒实验的基础上，讨论了后者的钯环的实际作用，该环与钯纳米颗粒的形成和活性参与密切相关。
• Efficient N-heterocyclic carbene nickel pincer complexes catalyzed cross coupling of benzylic ammonium salts with boronic acids
  作者：Xi-Yu Liu、Hai-Bo Zhu、Ya-Jing Shen、Jian Jiang、Tao Tu

  DOI：10.1016/j.cclet.2016.09.006

  日期：2017.2

  Abstract Pyridine-bridged bis-benzimidazolylidene nickel complexes exhibited very high catalytic activity toward cross coupling of inactive (hetero)aryl benzylic ammonium salts with (hetero)aryl and alkenyl boronic acids under mild reaction conditions. Even at 2 mol% catalyst loading, a wide range of substrates for both coupling partners with different steric and electronic properties were well tolerated

  摘要吡啶桥联的双苯并咪唑基亚乙基镍络合物在温和的反应条件下，对非活性（杂）芳基苄基铵盐与（杂）芳基和烯基硼酸的交叉偶联反应具有很高的催化活性。即使在催化剂负载量为2 mol％的情况下，两种具有不同空间和电子特性的偶合配偶体都可以很好地耐受各种底物。
• Nickel-Catalyzed Cross-Coupling of Anisoles with Alkyl Grignard Reagents via C–O Bond Cleavage
  作者：Mamoru Tobisu、Tsuyoshi Takahira、Naoto Chatani

  DOI：10.1021/acs.orglett.5b02200

  日期：2015.9.4

  Nickel-catalyzed cross-coupling of methoxyarenes with alkyl Grignard reagents, which involves the cleavage of the C(aryl)–OMe bond, has been developed. The use of 1,3-dicyclohexylimidazol-2-ylidene as a ligand allows the introduction of a variety of alkyl groups, including Me, Me3SiCH2, ArCH2, adamantyl, and cyclopropyl. The method can also be used for the alkylative elaboration of complex molecules

  已经开发了镍催化的甲氧基芳烃与烷基格氏试剂的交叉偶联，这涉及到C（芳基）-OMe键的裂解。使用1，3-二环己基咪唑-2-亚烷基作为配体允许引入各种烷基，包括Me，Me 3 SiCH 2，ArCH 2，金刚烷基和环丙基。该方法还可用于带有C（芳基）–OMe键的复杂分子的烷基化修饰。
• Gold(I)-catalyzed Benzylation of (Hetero)aryl Boronic Acids with (Hetero)benzyl Bromides by the Strategy of a S_N2-type Reaction
  作者：Wenqing Zang、Yin Wei、Min Shi

  DOI：10.1002/asia.201800923

  日期：2018.10.4

  gold‐catalyzed benzylation of (hetero)aryl boronic acids with (hetero)benzyl bromides to give the corresponding cross‐coupling products in moderate to good yields is reported. The reaction proceeds through a possible intermolecular SN2‐type reaction pathway to give a wide variety of di(hetero)arylmethanes as the desired products. An intriguing reaction mechanism has been proposed on the basis of control experiments

  在此，报道了第一个用（杂）苄基溴对（杂）芳基硼酸进行金催化的苄基化反应，以得到中等至良好收率的相应交叉偶联产物的实例。反应通过可能的分子间S N 2型反应路径进行，从而得到各种所需的二（杂）芳基甲烷。在控制实验，31 P-NMR光谱检测和DFT计算的基础上，提出了一种有趣的反应机理。
• Fluorous Oxime Palladacycle: A Precatalyst for Carbon–Carbon Coupling Reactions in Aqueous and Organic Medium
  作者：Woen Susanto、Chi-Yuan Chu、Wei Jie Ang、Tzyy-Chao Chou、Lee-Chiang Lo、Yulin Lam

  DOI：10.1021/jo202482h

  日期：2012.3.16

  To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for a wide range of carbon carbon bond formation reactions (Suzuki-Miyaura, Sonogashira, Stille, Heck, Glaser-type, and Kumada) in either aqueous or organic medium under microwave irradiation. Palladacycle 1 could be recovered through F-SPE in various coupling reactions with recovery ranging from 84 to 95% for the first cycle. Inductively coupled plasma optical emission spectrometry (ICP-OES) analyses of the Pd content in the crude product from each class of transformation indicated extremely low levels of leaching and the palladacycle could be reused four to five times without significant loss of activity.

表征谱图