2-ethyl-2'-methoxy-1,1'-biphenyl | 1384515-81-4

• 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-ethyl-2'-methoxy-1,1'-biphenyl
• 英文别名: 2-methoxy-2'-ethylbiphenyl；1-Ethyl-2-(2-methoxyphenyl)benzene
• CAS: 1384515-81-4
• 化学式: C₁₅H₁₆O
• 分子量: 212.291
• InChiKey: DHESYHSQBCJZDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-氯苯甲醚 、 bis(2-ethylphenyl)borinic acid 在 bis(triphenylphosphine)nickel(II) chloride 、 potassium phosphate monohydrate 、 1-丁基-3-甲基咪唑溴盐 作用下， 以 甲苯 为溶剂， 反应 10.0h， 以54%的产率得到2-ethyl-2'-methoxy-1,1'-biphenyl
  参考文献：
  名称：

  N-杂环卡宾辅助的双（膦）镍催化的二芳基硼酸与芳基氯化物，甲苯磺酸盐和氨基磺酸盐的交叉偶联

  摘要：

  二芳基硼酸与芳基氯化物，甲苯磺酸盐和氨基磺酸盐的高效双（膦）镍催化交叉偶联已经在由N，N'-二烷基咪唑鎓盐（例如N）原位生成的N-杂环卡宾（NHC）的帮助下进行了丁基- ñ '甲基咪唑溴化物（[BMIM] BR），在用k甲苯3 PO 4 ·3H 2 O为基础。与双（NHC）镍催化的传统Suzuki芳基硼酸偶联反应不同，Ni（PPh 3）2 Cl 2原位生成单（NHC）双（膦）镍物种/ [Bmim] Br在二芳基硼酸的交叉偶联中显示出高催化活性。发现二芳基硼酸的结构影响很小，而芳基氯化物，甲苯磺酸盐和氨基磺酸盐的电子因素则显着影响偶联。以1.5 mol％NiCl 2（PPh 3）2 / [Bmim] Br作为催化剂前体可以有效地实现电子活化的芳基氯化物，甲苯磺酸盐和氨基磺酸盐的偶联，从而以3-5 mol％的高收率得到联芳基产品。加载必须用于非激活和停用的耦合。小邻里芳基氯，甲苯磺酸酯和氨基磺

  DOI：

  10.1021/jo501291y

文献信息

• N-Heterocyclic Carbene-Assisted, Bis(phosphine)nickel-Catalyzed Cross-Couplings of Diarylborinic Acids with Aryl Chlorides, Tosylates, and Sulfamates
  作者：Haihua Ke、Xiaofeng Chen、Gang Zou

  DOI：10.1021/jo501291y

  日期：2014.8.1

  Ni(PPh3)2Cl2/[Bmim]Br displayed high catalytic activities in the cross-couplings of diarylborinic acids. The structural influences from diarylborinic acids were found to be rather small, while electronic factors from aryl chlorides, tosylates, and sulfamates affected the couplings remarkably. The couplings of electronically activated aryl chlorides, tosylates, and sulfamates could be efficiently effected with

  二芳基硼酸与芳基氯化物，甲苯磺酸盐和氨基磺酸盐的高效双（膦）镍催化交叉偶联已经在由N，N'-二烷基咪唑鎓盐（例如N）原位生成的N-杂环卡宾（NHC）的帮助下进行了丁基- ñ '甲基咪唑溴化物（[BMIM] BR），在用k甲苯3 PO 4 ·3H 2 O为基础。与双（NHC）镍催化的传统Suzuki芳基硼酸偶联反应不同，Ni（PPh 3）2 Cl 2原位生成单（NHC）双（膦）镍物种/ [Bmim] Br在二芳基硼酸的交叉偶联中显示出高催化活性。发现二芳基硼酸的结构影响很小，而芳基氯化物，甲苯磺酸盐和氨基磺酸盐的电子因素则显着影响偶联。以1.5 mol％NiCl 2（PPh 3）2 / [Bmim] Br作为催化剂前体可以有效地实现电子活化的芳基氯化物，甲苯磺酸盐和氨基磺酸盐的偶联，从而以3-5 mol％的高收率得到联芳基产品。加载必须用于非激活和停用的耦合。小邻里芳基氯，甲苯磺酸酯和氨基磺
• A mild robust generic protocol for the Suzuki reaction using an air stable catalyst
  作者：Jonathan D. Moseley、Paul M. Murray、Edward R. Turp、Simon N.G. Tyler、Ross T. Burn

  DOI：10.1016/j.tet.2012.05.030

  日期：2012.7

  A mild but robust procedure has been developed as a first pass generic protocol for the Suzuki-Miyaura reaction. The protocol employs an air stable palladium pre-catalyst at low loading (<= 1 mol %) in aqueous solvent mixtures at moderate temperature using potassium carbonate as base. Under these mild conditions, most aryl bromides will react with sterically and electronically demanding aryl boronic acids to give complete conversion to the product biphenyls in less than 1 h. Aryl chlorides are also fully converted in most cases either under identical conditions in 8-24 h, or in 2 h at elevated temperature. A further advantage of these mild conditions of moderate temperature, weak base and benign solvent is that sensitive functional groups and structural motifs are well tolerated. In addition, the lipophilic biphenyl products are readily isolated after a simple work-up procedure. These generic conditions are ideal for proof of transformation, and as the starting point for development and optimization of a specific process. The discovery and fine-tuning of this generic protocol will be presented, supported extensively by examples to illustrate its scope and utility. (C) 2012 Elsevier Ltd. All rights reserved.
• Long-Range Bonding/Nonbonding Interactions: A Donor–Acceptor Resonance Studied by Dynamic NMR
  作者：Renzo Ruzziconi、Susan Lepri、Federica Buonerba、Manfred Schlosser、Michele Mancinelli、Silvia Ranieri、Luca Prati、Andrea Mazzanti

  DOI：10.1021/acs.orglett.5b01152

  日期：2015.6.5

  Long-range bonding interactions were evaluated using variable-temperature NMR spectroscopy and suitable 2'-CH2X-substituted phenylpyridines (X = Me, NMe2, OMe, F). It was found that the arylpyridyl rotational barriers were lower when electronegative atoms were bound to the alpha carbon of the 2' moiety. This effect was ascribed to a stabilizing interaction in the transition state due to the lone pair of the heterocyclic nitrogen with the alpha carbon. Computational support for this hypothesis came from CCSD(T)/6-31+G(d) calculations. Steric effects of the X moiety were ruled out by comparison of the rotational barriers of analogous biphenyls.
• Nickel-Catalyzed Cross-Coupling of Diarylborinic Acids with Aryl Chlorides
  作者：Xiaofeng Chen、Haihua Ke、Gang Zou

  DOI：10.1021/cs4009946

  日期：2014.2.7

  high atom economy of diarylborinic acids and cost-effectiveness of the nickel/phosphine catalyst system make the cross-coupling truly practical in the production of biaryl fine chemicals. Usefulness of the nickel/phosphine catalyzed cross-coupling of diarylborinic acids with aryl chlorides has been demonstrated in the development of a scalable and economical process for synthesis of 4′-methyl-2-cyanobiphenyl

  已开发出一种高效的镍/三芳基膦催化剂体系Ni [P（4-MeOPh）3 ] 2 Cl 2 / 2P（4-MeOPh）3，用于二芳基硼酸与多种芳基氯化物的交叉偶联。在存在K 3 PO 4 ·3H 2的情况下，使用0.5–2 mol％的催化剂负载量，可以获得具有不同官能团和位阻的各种不对称联芳基和杂联芳基化合物甲苯中的O。二芳基硼酸的高原子经济性和镍/膦催化剂体系的成本效益使交叉偶联在联芳基精细化学品的生产中真正可行。镍/膦催化二芳基硼酸与芳基氯化物的交叉偶联的有用性已在开发可扩展且经济的合成4'-甲基-2-氰基联苯，Sartan联苯的方法的过程中得到证明。