(3',5'-二甲基-4-联苯基)甲醇 | 885963-96-2

• 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: (3',5'-二甲基-4-联苯基)甲醇
• 英文名称: (3',5'-dimethylbiphenyl-4-yl)methanol
• 英文别名: 4-(3,5-Dimethylphenyl)benzyl alcohol；[4-(3,5-dimethylphenyl)phenyl]methanol
• CAS: 885963-96-2
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: FGQPNLRLHZSJMO-UHFFFAOYSA-N

物化性质

• 沸点：
  352.1±21.0 °C(Predicted)
• 密度：
  1.055±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,5-二甲基溴苯 、 4-溴苄醇 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 双联邻苯二酚硼酸酯 、 potassium acetate 、 potassium phosphate monohydrate 作用下， 以 乙醇 、 乙二醇 、 二甲基亚砜 为溶剂， 反应 20.5h， 以41%的产率得到(3',5'-二甲基-4-联苯基)甲醇
  参考文献：
  名称：

  JP5770503

  摘要：

  公开号：

文献信息

• Palladium(II) complexes bearing 2-(1H-imidazol/oxazol-2-yl)-pyridines: Synthesis, structures and ligand effects in Suzuki–Miyaura cross-coupling
  作者：Abiodun Omokehinde Eseola、Daniel Geibig、Helmar Görls、Wen-Hua Sun、Xiang Hao、Joseph Anthony Orighomisan Woods、Winfried Plass

  DOI：10.1016/j.jorganchem.2013.12.041

  日期：2014.3

  P212121. All complexes were utilized as pre-catalysts in a comparative study to probe relevant features of the palladium active species during high temperature Suzuki–Miyaura cross-coupling catalysis. Relatively higher catalytic activities were obtained for complexes bearing the bidentate ligands that possess weaker azole donor arms. Results obtained suggest that ligand dissociation steps may be important

  一系列二氯化钯（Ⅱ）配合物（PD1 - Pd4ox）的基础上hemilabile 2-（1H-咪唑-2-基）吡啶和2-（恶唑-2-基）吡啶配体被合成和表征的衍生物。的配位体设计为引入各种电子和结构特征和晶体结构PD1，Pd1Me，器Pd3，和Pd3Me进行了测定。PD1和Pd1Me两者结晶的单斜晶系空间群C ^ 2 / C。Pd3在单斜空间群P 2 1 / c中结晶，而Pd3Me在正交空间群P 2 1 2 1 2 1中结晶。在一项比较研究中，所有配合物均被用作前催化剂，以探索高温Suzuki-Miyaura交叉偶联催化过程中钯活性物种的相关特征。对于带有带有较弱的唑供体臂的二齿配体的配合物，获得了相对较高的催化活性。获得的结果表明，配体解离步骤对于高效产生活性物质可能很重要。特别地，在所研究的系列中观察到的配体效应表明，对于配合物而言观察到更高的催化剂效率，对于该配合物，钯中心的配体配位很容易转化为单齿模式。
• Importance of monodentate mono-ligand designs in developing N-stabilized Pd catalysts for efficient ambient temperature C C coupling: Donor strengths and steric features
  作者：Abiodun Omokehinde Eseola、Helmar Görls、Winfried Plass

  DOI：10.1016/j.mcat.2019.110398

  日期：2019.8

  catalyst loading, 45 °C and within 15 min. On the other hand, the complexes with trans-bis-ligand coordination were inactive at ambient temperatures. Therefore, it was concluded that coordinative saturation, which results from implementing two or more ligand equivalents or use of polydentate ligands on palladium, should be strongly discouraged. Such saturation necessitates the undesirable and avoidable high

  不友好的温度曲线和碳偶联催化的成本，这对合成有机化学家和工业适用性均构成挑战，促使我们设计新的单齿N-供体作为支撑配体，目的是构建分子上与碳原子接近的环境温度预催化剂。假设的有效形式。因此，一系列的空间变化的单齿N-供体咪唑（的1 - 7）和恶唑（8 - 9）已被合成和它们的N-供体强度，将其估计为的pK一个S，被系统地从0.9通过变化至8.5取代基变化。十一种目标单配体络合物（1 -PdCl 2 MeCN –9 -PdCl 2的MeCN，6 -PdCl 2 PHCN和7 -PdCl 2 PHCN）和6个反式-双-配体复合物（1 2 -PdCl 2，2 2 -PdCl 2，3 2 -PdCl 2，6 2 -PdCl 2，分离出1 2 -Pd（OAc）2和2 2 -Pd（OAc）2）并与PdI 2（PPh 3）2一起进行催化研究。。通过原位“ Pd（II）盐+配体”方法和使用预催化剂进行的偶
• New Bidentate N-Sulfonyl-Substituted Aromatic Amines as Chelate Ligand Backbones: Pd Catalyst Generation in C–C Coupling via In Situ and Precatalyst Modes
  作者：Hammed Olawale Oloyede、Raymond Akong Akong、Joseph Anthony Orighomisan Woods、Helmar Görls、Winfried Plass、Abiodun Omokehinde Eseola

  DOI：10.1071/ch19668

  日期：——

  only Pd(OAc)2, the ligand-supported palladium species clearly possess positive catalytic advantage. Furthermore, Suzuki coupling efficiencies by 1 : 1 ‘Pd(OAc)2 + ligand’ yielded notably better outcomes than for the 1 : 2 ‘Pd(OAc)2 + ligand’ in situ catalyst generation, which reveals that coordinative saturation is undesirable. The size of the complementing monodentate co-ligand was observed to influence

  通过2-（氨基甲基）苯胺与磺酰氯试剂的缩合，分离出一系列基于N-（2-（R-磺酰胺基）苄基）R-磺酰胺的六个新的双齿配体作为阴离子或单阴离子螯合剂。R ＝甲基（1和1'），甲苯基（2和2'），2,4,6-三甲基苯基（3）或2,4,6-三异丙基苯基（4）。配位体的配合物2 - 4在室温下用钯反应（II在不同的单齿N-供共配体的存在下形成）乙酸乙酯配合物加入Pd 2（2dmap），加入Pd 2'（OAc.py），器Pd3（2acn），Pd3（2py），Pd4（2acn）和Pd4（2py），通过三个X射线晶体分析在结构上得到确认。在水中进行的催化研究结果表明，在钯催化剂负载量为0.2 mol％的情况下，在10分钟内高转换频率和高达98％的产率。相对于仅存在Pd（OAc）2的无配体催化，配体负载的钯物质显然具有积极的催化优势。此外，通过铃木偶联1的效率：1 '的Pd（OAC）2  +配体'显着产生
• N-donor-stabilized Pd(II) species supported by sulphonamide-azo ligands: Ligand architecture, solvent co-ligands, C–C coupling
  作者：Hammed Olawale Oloyede、Joseph Anthony Orighomisan Woods、Helmar Görls、Winfried Plass、Abiodun Omokehinde Eseola

  DOI：10.1016/j.molstruc.2019.127030

  日期：2020.1

  were prepared and examined as organic ligands for stabilizing palladium active centers; R = methyl, tolyl or triiso-propylphenyl. Palladium complexes, which were obtained in varying coordination environments as well as with varying complementary co-ligands (water, acetonitrile or pyridine), have been subjected to Suzuki and Heck coupling experiments in order to study molecular level ligand effects on

  摘要 在本报告中，制备了一系列合成价格合理的无膦配体（L1-L4），形式为 RSO2-NH-Ph-NN-Ph-NH-SO2R，作为稳定钯活性中心的有机配体；R = 甲基、甲苯基或三异丙基苯基。在不同的配位环境以及不同的互补共配体（水、乙腈或吡啶）中获得的钯配合物已进行 Suzuki 和 Heck 偶联实验，以研究分子水平配体对优选催化剂设置的影响。由螯合配体产生的钯物种记录了 Suzuki 和 Heck 与官能团耐受性偶联的显着偶联活性。结果表明，尽管这些偶氮苯配体具有三齿螯合特性，在磺酰基上引入大单元使得能够产生具有高周转频率的活性钯物种；例如，在 5 分钟内以 0.2 mol % Pd.L2.py 负载量在仅作为溶剂的水中进行 5040 h-1（84% 产率）。获得了催化效率与配位共配体的体积之间的相关性。然而，虽然 Suzuki 偶联活性随着预形成复合物（即水
• Cyclometallation, steric and electronic tendencies in a series of Pd(II) complex pre-catalysts bearing imidazole–phenol ligands and effects on Suzuki–Miyaura catalytic efficiencies
  作者：Abiodun O. Eseola、Helmar Görls、Joseph A.O. Woods、Winfried Plass

  DOI：10.1016/j.molcata.2015.06.001

  日期：2015.9

  A series of new structurally and electronically diversified palladium complexes derived from seven less sterically crowded 2-(4,5-diinethyl-1H-imidazol-2-yl) pheno1/2-(4,5-diethyl-1H-imidazol-2-yl) phenol ligands and fourteen 2-(4,5-diphenyl-1H-imidazol-2-yl) phenols/2-(1H-phenanthro[9,10-d]imidazol-2-yl) phenols bearing varying degrees of higher steric bulk have been prepared and characterized. While single crystals grown from precipitated products of complexation reactions confirmed the bis-ligand Pd(NO)(2) coordination, few crystals obtained from reaction filtrates involving the 244,5-diphenyl-1H-imidazol-2-yl) phenols provided evidence for formation of N (O) over cap(C) over cap chelation species achieved by cyclometallation. Results from structural analyses and catalytic outcomes generally indicate that desirable variables on the ligand frameworks for obtaining superior catalyst activities either provides hemilabile or sterically strained chelation characters, which would both favour generation of monodentate coordination species at the catalysis temperature. In particular, correlation was observed between tendency for cyclometallation in the palladium complexes and poor Suzuki-Miyaura catalytic prospects. Based on hopeful activity obtained for the complex bearing 4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl) phenol, it was also concluded that sterically bulky ligand is not a necessity for high coupling efficiency, while presence of potentially cyclometallating substituent moieties in the vicinity of the palladium centre may in fact destroy catalytic prospects. (C) 2015 Elsevier B.V. All rights reserved.