1-([1,1'-biphenyl]-2-yl)-2-methylnaphthalene

• 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: 1-([1,1'-biphenyl]-2-yl)-2-methylnaphthalene
• 英文别名: (S)-1-(2'-biphenyl)-2-methylnaphthalene；2-Methyl-1-(2-phenylphenyl)naphthalene；2-methyl-1-(2-phenylphenyl)naphthalene
• 化学式: C₂₃H₁₈
• 分子量: 294.396
• InChiKey: ZROLQIKMXYJMGC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 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-溴-2-萘酚 在 4-二甲氨基吡啶 、 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 1,2-双(二苯基膦)乙烷氯化镍 、 (R)-AntPhos 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 以 1,4-二氧六环 、 乙醚 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 42.67h， 生成 1-([1,1'-biphenyl]-2-yl)-2-methylnaphthalene
  参考文献：
  名称：

  通过动态动力学阻转选择性铃木-宫浦交叉偶联开发用于联芳阻转异构体合成的联芳基半硼酸酯

  摘要：

  我们在此引入联芳基半硼酸酯作为一种新型桥连联芳基试剂，用于不对称合成轴向手性联芳基结构，并开发了钯催化的联芳基半硼酸酯的不对称铃木-宫浦交叉偶联。这种动态的间质选择性偶联反应表现出高对映选择性、良好的官能团耐受性和广泛的底物范围。通过产物的转化和手性聚芳烃的程序合成证明了当前方法的合成应用。初步机理研究表明，该反应通过对映体决定的动态动力学atroposelective金属转移步骤进行。

  DOI：

  10.1021/jacs.3c14450

文献信息

• Hindered Aryllithium Reagents as Partners in Palladium-Catalyzed Cross-Coupling: Synthesis of Tri- and Tetra-<i>ortho</i>-Substituted Biaryls under Ambient Conditions
  作者：Massimo Giannerini、Valentín Hornillos、Carlos Vila、Martín Fañanás-Mastral、Ben L. Feringa

  DOI：10.1002/anie.201306427

  日期：2013.12.9

  lithium reagent: Mono‐ and di‐ortho‐substituted aryllithium reagents were coupled through palladium catalysis with hindered aryl bromides to form highly congested tri‐ and tetra‐ortho‐substituted biaryls. The reaction allows the use of easily accessible ortho‐functionalized aryllithium compounds. The high reactivity of organolithium reagents facilitates a fast process under ambient conditions.

  优雅像蝴蝶，像锂试剂螫：单-和二-邻-取代的芳基锂试剂通过与受阻芳基溴化物钯催化偶联，以形成高度拥挤的三-和四-邻-取代的联芳基。该反应允许使用易于获得的邻官能化芳基锂化合物。有机锂试剂的高反应活性有助于在环境条件下进行快速处理。
• An enantioselective artificial Suzukiase based on the biotin–streptavidin technology
  作者：Anamitra Chatterjee、Hendrik Mallin、Juliane Klehr、Jaicy Vallapurackal、Aaron D. Finke、Laura Vera、May Marsh、Thomas R. Ward

  DOI：10.1039/c5sc03116h

  日期：——

  Introduction of a biotinylated monophosphine palladium complex within streptavidin affords an enantioselective artificial Suzukiase. Site-directed mutagenesis allowed the optimization of the activity and the enantioselectivity of this artificial metalloenzyme. A variety of atropisomeric biaryls were produced in good yields and up to 90% ee.

  将生物素化的单磷酸钯配合物引入链霉亲合素中，形成对映选择性的人工银催化剂。通过位点定向突变优化了这种人工金属酶的活性和对映选择性。产率良好，对映纯度高达90%，产生了多种二苯基异构体。
• Design and Discovery of Water-Soluble Benzooxaphosphole-Based Ligands for Hindered Suzuki–Miyaura Coupling Reactions with Low Catalyst Load
  作者：Arun D. R. Shada、Hari P. R. Mangunuru、Leila Terrab、Srinivasarao Tenneti、Nageswara Rao Kalikinidi、Santhosh Reddy Naini、Praveen Gajula、Emily B. Crull、Venumadhav Janganati、Raghavendra Kovvuri、Vasudevan Natarajan、Daniel Lee、Jinya Yin、Lalith Samankumara、Rohit Mahar、Xueyi Zhang、Anji Chen、Chathuranga C. Hewa-Rahinduwage、Zhirui Wang、Manasa Mamunooru、Jagruti Rana、Chaitanya S. Wannere、Joseph D. Armstrong、R. Thomas Williamson、Gopal Sirasani、Bo Qu、Chris H. Senanayake

  DOI：10.1021/acs.orglett.3c01663

  日期：2024.4.12

  benzooxaphosphole-based, water-soluble ligands in the application of Suzuki–Miyaura cross-coupling reactions for sterically hindered substrates in aqueous media. The catalytic activities of the coupling reactions were greatly enhanced by the addition of catalytic amounts of organic phase transfer reagents, such as tetraglyme and tetrabutylammonium bromide. The optimized general protocol can be conducted

  我们报告了一类新型高效、基于苯并氧磷的水溶性配体，用于水介质中空间位阻底物的铃木-宫浦交叉偶联反应的应用。通过添加催化量的有机相转移试剂，例如四甘醇二甲醚和四丁基溴化铵，大大增强了偶联反应的催化活性。优化的通用方案可以在低催化剂负载下进行，从而为这些反应提供了实用的解决方案。这种新的铃木-宫浦方案的可行性通过各种底物得到了证明，可以生成重要的构建模块，包括杂环化合物，用于合成生物活性化合物。
• Chiral PEPPSI Complexes: Synthesis, Characterization, and Application in Asymmetric Suzuki–Miyaura Coupling Reactions
  作者：Laure Benhamou、Céline Besnard、E. Peter Kündig

  DOI：10.1021/om4009982

  日期：2014.1.13

  PEPPSI complexes incorporating chiral N-heterocyclic carbene (NHC) ligands based on 2,2-dimethyl-1-(o-substituted aryl)-propan-1-amines were synthesized. Two complexes, with one saturated and one unsaturated NHC ligand, were structurally characterized. The chiral PEPPSI complexes were used in asymmetric Suzuki-Miyaura reactions, giving atropisomeric biaryl products in modest to good enantiomeric ratios.
• <i>C</i>₂-Symmetric Bis-Hydrazones as Ligands in the Asymmetric Suzuki−Miyaura Cross-Coupling
  作者：Antonio Bermejo、Abel Ros、Rosario Fernández、José M. Lassaletta

  DOI：10.1021/ja8074693

  日期：2008.11.26

  Glyoxal bis-hydrazone derived from (S,S)-1-amino-2,5-diphenytpyrrolidine behaves as an excellent ligand for phosphine-free, asymmetric Suzuki-Miyaura cross couplings, thereby affording a variety of enantiomerically enriched biaryls with different substitution patterns. The high catalytic activity of the [PdCl2(bis-hydrazone)] complex allows reactions to be performed at room temperature, affording products with excellent enantioselectivities in all cases.