2',4',6'-trimethylbiphenyl-4-carboxylic acid ethyl ester | 66818-60-8

• 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: 2',4',6'-trimethylbiphenyl-4-carboxylic acid ethyl ester
• 英文别名: ethyl 2',4',6'-trimethyl-[1,1'-biphenyl]-4-carboxylate；ethyl 2',4',6'-trimethylbiphenyl-4-carboxylate；2',4',6'-Trimethyl-biphenyl-4-carbonsaeure-ethylester；[1,1'-Biphenyl]-4-carboxylic acid, 2',4',6'-trimethyl-, ethyl ester；ethyl 4-(2,4,6-trimethylphenyl)benzoate
• CAS: 66818-60-8
• 化学式: C₁₈H₂₀O₂
• 分子量: 268.356
• InChiKey: PRCAPDAPOMXCPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4'-bromo-2,4,6-trimethylbiphenyl 在 氯化亚砜 作用下， 生成 2',4',6'-trimethylbiphenyl-4-carboxylic acid ethyl ester
  参考文献：
  名称：

  Haefelinger,G. et al., Chemische Berichte, 1978, vol. 111, p. 1323 - 1329

  摘要：

  DOI：

文献信息

• Gold(<scp>i</scp>)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes
  作者：Manjur O. Akram、Popat S. Shinde、Chetan C. Chintawar、Nitin T. Patil

  DOI：10.1039/c8ob00630j

  日期：——

  Gold(I)-catalyzed cross-coupling reactions of aryldiazonium salts with organostannanes are described. This redox neutral strategy offers an efficient approach to diverse biaryls, vinyl arenes and arylacetylenes. Monitoring the reaction with NMR and ESI-MS provided strong evidence for the in situ formation of Ph3PAuIR (R = aryl, vinyl and alkynyl) species which is crucial for the activation of aryldiazonium

  描述了金（I）催化的芳基重氮盐与有机锡烷的交叉偶联反应。这种氧化还原中性策略为各种联芳基，乙烯基芳烃和芳基乙炔提供了一种有效的方法。用NMR和ESI-MS监测反应为原位形成Ph 3 PAu I R（R =芳基，乙烯基和炔基）物种提供了有力证据，这对于激活芳基重氮盐至关重要。
• [Pd(Cl)2{P(NC5H10)(C6H11)2}2]-A Highly Effective and Extremely Versatile Palladium-Based Negishi Catalyst that Efficiently and Reliably Operates at Low Catalyst Loadings
  作者：Jeanne L. Bolliger、Christian M. Frech

  DOI：10.1002/chem.201001201

  日期：——

  electronically activated, non‐activated, deactivated, sterically hindered, heterocyclic, and functionalized aryl bromides with various (also heterocyclic) arylzinc reagents, typically within a few minutes at 100 °C in the presence of just 0.01 mol % of catalyst. Aryl bromides containing nitro, nitrile, ether, ester, hydroxy, carbonyl, and carboxyl groups, as well as acetals, lactones, amides, anilines,

  [Pd（Cl）2 P（NC 5 H 10）（C 6 H 11）2 } 2 ]（1）已通过使市售的[Pd（cod）（Cl）2 ]反应定量制备。室温下在几分钟内在N 2中与易于制备的1-（二环己基膦酰基）哌啶在甲苯中的环辛二烯）。综合大楼1已被证明是极佳的Negishi催化剂，能够将各种电子活化，非活化，失活，空间受阻，杂环和官能化的芳基溴化物与各种（也是杂环的）芳基锌试剂定量偶联，通常在几分钟内即可完成。 100°C，仅存在0.01 mol％的催化剂。含有硝基，腈，醚，酯，羟基，羰基和羧基的芳基溴化物，以及缩醛，内酯，酰胺，苯胺，烯烃，羧酸，乙酸，吡啶和嘧啶已被成功用作偶联伙伴。此外，在两个反应伙伴中都可以容忍电子和空间变化。实验观察强烈表明分子机制是有效的。
• Perylenequinonoid-catalyzed photoredox activation for the direct arylation of (het)arenes with sunlight
  作者：Shiwei Zhang、Zhaocheng Tang、Wenhao Bao、Jia Li、Baodang Guo、Shuping Huang、Yan Zhang、Yijian Rao

  DOI：10.1039/c9ob00659a

  日期：——

  and photobiology. However, their applications in photocatalysis are yet to be explored. We report here that sunlight along with 1 mol% cercosporin, which is one of the perylenequinonoid pigments, catalyzes the direct C–H bond arylation of (het)arenes by a photoredox process with good regioselectivity and broad functional group compatibility. Furthermore, a gram-scale reaction with great conversions

  天然存在的per醌类颜料（PQP）由于其出色的光敏性能而备受关注。作为光物理和光生物学的一个方面，它们已被广泛研究。然而，它们在光催化中的应用尚待探索。我们在这里报告说，阳光与1 mol％的头孢菌素（一种ylene醌类颜料之一）通过光氧化还原过程以良好的区域选择性和广泛的官能团相容性催化（杂）芳烃的直接C–H键芳基化。此外，即使通过含头孢菌素的上清液在液体发酵后不进行有机溶剂萃取和纯化的情况下，也实现了具有很大底物转化率的克级反应。
• Dual gold and photoredox catalysed C–H activation of arenes for aryl–aryl cross couplings
  作者：V. Gauchot、D. R. Sutherland、A.-L. Lee

  DOI：10.1039/c6sc05469b

  日期：——

  A mild and fully catalytic aryl–aryl cross coupling via gold-catalysed C–H activation has been achieved by merging gold and photoredox catalysis. The procedure is free of stoichiometric oxidants and additives, which were previously required in gold-catalysed C–H activation reactions. Exploiting dual gold and photoredox catalysis confers regioselectivity via the crucial gold-catalysed C–H activation

  通过结合金和光氧化还原催化，通过金催化的 C-H 活化实现了温和且完全催化的芳基-芳基交叉偶联。该过程不含以前金催化 C-H 活化反应所需的化学计量氧化剂和添加剂。利用金和光氧化还原双重催化通过关键的金催化 C-H 活化步骤赋予区域选择性，这在非选择性光催化对应物中不存在。
• Revealing a Second Transmetalation Step in the Negishi Coupling and Its Competition with Reductive Elimination: Improvement in the Interpretation of the Mechanism of Biaryl Syntheses
  作者：Qiang Liu、Yu Lan、Jing Liu、Gang Li、Yun-Dong Wu、Aiwen Lei

  DOI：10.1021/ja903277d

  日期：2009.7.29

  generates Ar(2)PdAr(2) and Ar(1)ZnCl, which upon reductive elimination and hydrolysis, respectively, give the homocoupling product Ar(2)-Ar(2) and the dehalogenation product Ar(1)H. The ratio of the cross-coupling product Ar(1)-Ar(2) and the homocoupling product Ar(2)-Ar(2) is determined by competition between the second transmetalation and reductive elimination steps. This mechanism is further supported

  本文介绍了 Pd 催化的 Negishi 偶联反应的实验和理论研究，并揭示了 Ar(1)-Pd-Ar(2) 物种与有机锌试剂 Ar(2)-ZnX 之间的新型第二次金属转移反应。对这第二步的理解揭示了均偶联和脱卤产物是如何形成的。因此，第二次金属转移生成 Ar(2)PdAr(2) 和 Ar(1)ZnCl，它们分别在还原消除和水解后得到均偶联产物 Ar(2)-Ar(2) 和脱卤产物 Ar(1) ）H。交叉偶联产物 Ar(1)-Ar(2) 和均偶联产物 Ar(2)-Ar(2) 的比率由第二次金属转移和还原消除步骤之间的竞争决定。这种机制得到了密度泛函理论计算的进一步支持。