1,2-双(4-甲基苯基)苯 | 64586-14-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1,2-双(4-甲基苯基)苯
• 英文名称: 4,4''-dimethyl-(1,1',2',1'')-terphenyl
• 英文别名: 1,2-di(p-methylphenyl)benzene；1,1':2',1''-Terphenyl, 4,4''-dimethyl-；1,2-bis(4-methylphenyl)benzene
• CAS: 64586-14-7
• 化学式: C₂₀H₁₈
• 分子量: 258.363
• InChiKey: YWBQRFZBFNEBRX-UHFFFAOYSA-N

物化性质

• 熔点：
  96-97 °C
• 沸点：
  368.7±22.0 °C(Predicted)
• 密度：
  1.022±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  1,2-di-p-tolylcyclohex-4-ene-1,2-diol 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 3.0h， 以76%的产率得到1,2-双(4-甲基苯基)苯
  参考文献：
  名称：

  闭环复分解方法合成邻三联苯衍生物

  摘要：

  据报道，使用闭环复分解（RCM）作为关键步骤，从苯甲醚合成邻-叔苯基的方法。合成了具有卤素取代基的邻-三联苯，可以通过交叉偶联反应将其进一步官能化。联苯撑的合成证明了该方法的合成效用。

  DOI：

  10.1002/ejoc.201900988

文献信息

• Substituent-dependent structures and catalysis of benzimidazole-tethered N-heterocyclic carbene complexes of Ag(i), Ni(ii) and Pd(ii)
  作者：Fuwei Li、Jian Jin Hu、Lip Lin Koh、T. S. Andy Hor

  DOI：10.1039/c000722f

  日期：——

  Homoleptic cationic benzimidazole-imidazolin-2-ylidene N-heterocyclic carbene (NHC = L) complexes of NiII and PdII have been prepared directly from the ligand precursor in salt form [H.L]Cl and from the transmetallation route via AgI. The N-tether of the imidazolinylidene ring imposes a significant influence on the nuclearity of the intermediate Ag(I)-NHC complexes and the geometric isomer outcome of the d8 products. Use of a benzyl-substituted NHC gives [Ag4(LBn)2Cl4], 2a (from [HLBn]Cl, 1a, and Ag2O) (Bn = benzyl), which shows an alignment of four silver atoms bridged by the difunctional C–N ligands and chlorides. Its transmetallation with NiCl2(PPh3)4 and PdCl2(MeCN)2 results in double-metal salts 2[M(LBn)2]2+[Ag4Cl8]4− (M = Ni (3a) and Pd (4a)). The nuclearity of the Ag4 aggregate is maintained in the transmetallation process. Their Ag-free forms [M(LBn)2]Cl2 (M = Ni (5) and Pd (6)) were prepared by direct deprotonation of 1a with M(OAc)2. The two carbenic carbon donor are cis- to each other in both 3a and 4a, thus imposing the weaker σ-benzimidazole nitrogen donor to be trans to them. A sterically demanding mesityl pendant however gives the dinuclear dissymmetic [Ag2(LMes)2Cl2], 2b (Mes = mesityl) that shows a 12-membered metallomacrocyclic ring with a 2-coordinated [AgI(NHC)2] and 4-coordinated [AgI(Imd)2Cl2] (Imd = imidazole). Transmetallation of the latter, or direct metallation from [HLMes]Cl, 1b, gives [M(LMes)2]Cl2 (M = Ni (3b) and Pd (4b)) with the two carbonic carbon trans to each other. The catalytic potential of 3b and 4b, which are more effective than 5 and 6, has been demonstrated by their high activities in Ni-catalyzed Kumada at room temperature and Pd-catalyzed Heck couplings of aryl and/or heteroaryl halides, respectively.

  均配正离子苯并咪唑-咪唑啉亚基N-杂环卡宾（NHC = L）NiII和PdII配合物可以通过盐形式的配体前驱体[H.L]Cl以及通过AgI的转金属路线来直接制备。咪唑啉亚基环的N-连接对中间体Ag(I)-NHC配合物的核数和d8产物的几何异构体结果产生了显著影响。使用苯甲基取代的NHC得到[Ag4(LBn)2Cl4]，2a（由[HLBn]Cl，1a，和Ag2O制备）（Bn = 苯甲基），显示出四个银原子通过双功能的C-N配体和氯化物桥接的对齐。其与NiCl2(PPh3)4和PdCl2(MeCN)2的转金属反应得到了双金属盐2[M(LBn)2]2+[Ag4Cl8]4-（M = Ni (3a) 和 Pd (4a)）。Ag4聚集体的核数在转金属过程中得以保持。它们的Ag-free形式[M(LBn)2]Cl2（M = Ni (5) 和 Pd (6)）是通过1a与M(OAc)2的直接去质子化制备的。两个卡宾碳供体在3a和4a中都是cis相对的，因此使较弱的σ-苯并咪唑氮供体与其相对。然而，空间位阻较大的甲基苯基悬挂物给出了二核不对称的[Ag2(LMes)2Cl2]，2b（Mes = 甲基苯基），显示出具有2配位的[AgI(NHC)2]和4配位的[AgI(Imd)2Cl2]（Imd = 咪唑）的12元金属大环。后者的转金属反应，或直接从[HLMes]Cl，1b，金属化得到了[M(LMes)2]Cl2（M = Ni (3b) 和 Pd (4b)），其中两个碳碳彼此相对。3b和4b的催化潜力，它们比5和6更有效，已经通过它们在室温下Ni催化的Kumada和Pd催化的芳基和/或杂芳基卤化物的Heck偶联反应中的高活性得到了证明。
• Nanocrystalline Titania-Supported Palladium(0) Nanoparticles for Suzuki-Miyaura Cross-Coupling of Aryl and Heteroaryl Halides
  作者：B. Sreedhar、Divya Yada、P. Surendra Reddy

  DOI：10.1002/adsc.201100012

  日期：2011.10

  The Suzuki cross-coupling reaction of various aryl and heteroaryl halides with arylboronic and heteroarylboronic acids was studied using a titania-supported palladium(0) catalyst at room temperature under air. The conversion and selectivity results obtained for many substrates were excellent and similar to those provided by more active or even homogeneous catalysts. The methodology is similarly effective

  使用二氧化钛负载的钯（0）催化剂在室温下于空气中研究了各种芳基和杂芳基卤化物与芳基硼酸和杂芳基硼酸的Suzuki交叉偶联反应。对于许多底物，获得的转化率和选择性结果极好，与活性更高甚至均相的催化剂所提供的结果相似。使用2-溴-3,4,5-三甲氧基苯甲醛作为偶合伙伴，该方法同样有效，并获得了高收率的产品。此外，已表明其可用于合成三联苯和四联苯。通过简单的过滤从反应中定量回收催化剂，并重复使用多个循环，而活性没有明显损失。
• Palladium (II)–Salan Complexes as Catalysts for Suzuki–Miyaura C–C Cross-Coupling in Water and Air. Effect of the Various Bridging Units within the Diamine Moieties on the Catalytic Performance
  作者：Szilvia Bunda、Krisztina Voronova、Ágnes Kathó、Antal Udvardy、Ferenc Joó

  DOI：10.3390/molecules25173993

  日期：——

  salan ligands were synthesized by hydrogenation and subsequent sulfonation of salens (N,N’-bis(slicylidene)ethylenediamine and analogues) with various bridging units (linkers) connecting the nitrogen atoms. Pd (II) complexes were obtained in reactions of sulfosalans and [PdCl4]2−. Characterization of the ligands and complexes included extensive X-ray diffraction studies, too. The Pd (II) complexes proved

  水溶性的 salan 配体是通过对具有连接氮原子的各种桥接单元（接头）的 salens（N，N'-双（亚硅基）乙二胺和类似物）进行氢化和随后的磺化来合成的。Pd (II) 配合物是在硫柳胺和 [PdCl4]2- 的反应中获得的。配体和配合物的表征也包括广泛的 X 射线衍射研究。Pd (II) 配合物被证明是芳基卤化物和芳基硼​​酸衍生物在 80°C 下在水和空气中的 Suzuki-Miyaura 反应的高活性催化剂。对 Pd (II)-磺胺嘧啶催化剂的比较研究表明，催化活性随着接头长度的增加和配体 N 供体原子周围空间拥挤度的增加而大大增加；最高比活为40,000（mol底物）（mol催化剂×h）-1。
• Trinuclear copper(I) complex of 1,3-bis(2-pyridinylmethyl)imidazolylidene as a carbene-transfer reagent for the preparation of catalytically active nickel(II) and palladium(II) complexes
  作者：Chao Chen、Huayu Qiu、Wanzhi Chen

  DOI：10.1016/j.jorganchem.2011.09.008

  日期：2012.1

  each Cu–Cu bond capped by an imidazolylidene group. Each imidazolylidene acts as a bridging ligand in a μ2 mode and is bonded equally to two Cu(I) ions. The pincer nickel and palladium complexes are square-planar and contain a tridentate NCN ligand. Complexes 3 and 4 are efficient catalyst precursors for Kumada–Corriu and Suzuki–Miyaura coupling reactions of aryl halides with organometallic reagents

  1,3-双（吡啶-2-基甲基）-1H-咪唑-3-六氟磷酸盐（[HL1]（PF 6），L1 = 1,3-双（吡啶-2-基甲基）咪唑基亚烷基）的反应1,3-双（吡啶-2-基甲基）-1H-苯并咪唑-3-六氟磷酸盐（[HL2]（PF 6），L2 = 1,3-双（吡啶-2-基甲基）苯并咪唑基亚苄基）乙腈容易产生三核络合物[Cu 3（L1）3（PF 6）3 ]（1）和[Cu 3（L2）3（PF 6）3 ]（2）。Ni（PPh 3）2 Cl 2处理1由于过金属化作用，Pd（cod）Cl 2和[Pd（cod）Cl 2分别得到[Ni（L1）Cl]（PF 6）（3）和[Pd（L1）Cl]（PF 6）（4）。从[Cu 3（L1）3（PF 6）3 ]和阮内镍在乙腈中的反应获得[Ni（L1）2 ]（PF 6）2（5）。所有这些复合物已被充分表征。既1和2组成的三角形的Cu 3芯与由imidazolylidene基团
• Immobilization of an Aminobisphosphine–Pd ^II Complex over Graphene Oxide: An Efficient and Reusable Catalyst for Suzuki–Miyaura, Ullmann Coupling and Cyanation Reactions
  作者：Debasish Sengupta、Madhusudan K. Pandey、Dipanjan Mondal、Latchupatula Radhakrishna、Maravanji S. Balakrishna

  DOI：10.1002/ejic.201800291

  日期：2018.8.7

  on GO. The composite material showed high catalytic activity in Suzuki–Miyaura, Ullmann coupling and cyanation reactions. The heterogeneity of the composite was confirmed by a hot filtration test. The immobilized PNP–PdII shows comparable activity to its homogeneous analogue 2. The recycling ability of the catalyst was examined for five consecutive runs, which showed little or no reduction in its catalytic

  氨基双（膦）-Pd II络合物（PNP-Pd II）[PdCl 2 （Ph 2 P）2 N（CH 2）3 Si（OMe）3 }]（2）的接枝通过在2的甲氧基硅烷基与GO的羟基之间的缩合反应进行。通过FTIR光谱，固态31 P NMR光谱，SEM，TEM，XPS和ICP-AES技术对复合材料进行了表征。所有这些工具都支持化合物2的清洁固定在GO上。该复合材料在Suzuki-Miyaura，Ullmann偶联和氰化反应中显示出高催化活性。通过热过滤试验证实了复合材料的不均匀性。固定化的PNP-Pd II具有与其同类类似物2相当的活性。在连续五次运行中检查了催化剂的循环能力，显示其催化效率几乎没有或没有下降。