2-methoxy-2'-nitrobiphenyl | 6460-92-0

• 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-methoxy-2'-nitrobiphenyl
• 英文别名: 2-methoxy-2′-nitrobiphenyl；2-methoxy-2'-nitro-1,1'-biphenyl；2'-Nitro-2-methoxy-biphenyl；1,1'-Biphenyl, 2-methoxy-2'-nitro-；1-(2-methoxyphenyl)-2-nitrobenzene
• CAS: 6460-92-0
• 化学式: C₁₃H₁₁NO₃
• 分子量: 229.235
• InChiKey: LUAAEXWZEIXKHQ-UHFFFAOYSA-N

物化性质

• 熔点：
  80-81 °C
• 沸点：
  327.7±17.0 °C(Predicted)
• 密度：
  1.202±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methoxy-2'-nitrobiphenyl 在 indium 、 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene hydrochloride 、 双氧水 、 palladium diacetate 、 氯化铵 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 7.0h， 生成 9-acetyl-4-methoxycarbazole
  参考文献：
  名称：

  2-氨基联苯串联CH活化和CN键形成直接合成咔唑支架

  摘要：

  设计并研究了一种合成咔唑支架的有效方法。该方法被开发用于通过游离胺基团和芳烃的分子内组合来生产取代的咔唑。该方法的步骤包括串联 Pd 催化的 C-H 活化和分子内 C-N 键的形成。该方法显示出良好的官能团耐受性，并且取代基可以在2-氨基联苯底物的两个环中的任何一个或两个环上。闭环后，还原的 Pd 催化剂被过氧化氢氧化成 PdII。新方法也被证明可以很好地与相应的 2-N-乙酰氨基联苯一起使用。

  DOI：

  10.1002/ejoc.201601191
• 作为产物：
  描述：

  2-溴苯甲醚 在 正丁基锂 、 bis(triphenylphosphine)palladium(II) dichloride 、 potassium carbonate 作用下， 以 异丙醇 为溶剂， 反应 12.0h， 生成 2-methoxy-2'-nitrobiphenyl
  参考文献：
  名称：

  Magnesium and Calcium Complexes Containing Biphenyl-Based Tridentate Iminophenolate Ligands for Ring-Opening Polymerization of rac-Lactide

  摘要：

  A series of racemic 2-[(2'-methoxybiphenyl-2-ylimino)methyl]-4-R-2-6-R-1-phenols ((LH)-H-1-(LH)-H-8) were reacted with {Mg[N(SiMe3)(2)](2)}(2) and Ca[N(SiMe3)(2)](2)center dot 2THF (THF = tetrahydrofuran), respectively, to provide nine heteroleptic magnesium complexes L1-8MgN(SiMe3)(2) [R-1 = P-i(r), R-2 = H (1a); = Bu-t, R-2 = Me (2a and 2a center dot THF); R-1 = R-2 = Bu-t (3a); R-1 = R-2 = CMe2Ph (4a); R-1 = CPh3, R-2 = Bu-t (5a); R-1 = 1-piperidinylmethyl, R-2 = Bu-t (6a); R-1 = Cl, R-2 = Bu-t (7a); R-1 = Br, R-2 = Bu-t (8a)], two homoleptic calcium complexes (L-2,L-5)(2)Ca (2b and 5b), and one heteroleptic calcium complex [(L-4)CaN(SiMe3)(2)center dot THF] (4b), which have been fully characterized. In the solid state, magnesium complexes 2a and 6a are isostructural, and each possesses a monomeric structure, while magnesium complexes 7a and 8a are dimeric, where the two metal centers are bridged by two phenolate oxygen atoms of the ligands. The coordination geometry around the magnesium center in these complexes can be best described as a distorted tetrahedral geometry. Although bearing the same iminophenoloate ligand, the molecular structures of complexes 2a and 2a center dot THF are different from each other. In complex 2a center dot THF, the coordination of one molecule of THF to the magnesium atom leads to dissociation of the methoxy group of the ligand from the metal center. The homoleptic calcium complex 2b has a six-coordinate metal core ligated by all six donor atoms of two iminophenolate ligands. The heteroleptic magnesium complexes 1a-8a and calcium complex 4b proved to be efficient initiators for the ring-opening polymerization of rac-lactide at ambient temperature in THF or at 70 degrees C in toluene, and the polymerizations were better controlled in the presence of 2-propanol. The introduction of a bulky ortho substituent on the phenoxy unit of the ligand resulted in an increase of the catalytic activity of the corresponding metal complex. Microstructure analysis of the resultant poly(rac-lactide) samples via homonuclear-decoupled H-1 NMR spectroscopy revealed P-r values ranging from 0.60 to 0.81, which closely depended on the employed catalyst and polymerization conditions.

  DOI：

  10.1021/ic4012668

文献信息

• Method For Decarboxylating C-C Cross-Linking Of Carboxylic Acids With Carbon Electrophiles
  申请人：Goossen Lukas

  公开号：US20080177114A1

  公开（公告）日：2008-07-24

  The invention relates to a method for decarboxylating C—C bond formation by reacting carboxylic salts with carbon electrophiles in the presence of transition metal compounds as catalysts. The method represents a decarboxylating C—C bond formation of carboxylic acid salts with carbon electrophiles, wherein the catalyst contains two transition metals and/or transition metal compounds, from which one is present, preferably, in the oxidation step, which are different from each other by one unit, and catalyzes a radical decarboxylation which is absorbed during the second oxidation steps, which are different from each other by two units and catalyzes the two electron processes of a C—C bond formation reaction.

  该发明涉及一种方法，通过在过渡金属化合物存在的情况下，将羧酸盐与碳亲电体反应以脱羧基C—C键形成。该方法代表了一种羧酸盐与碳亲电体的脱羧基C—C键形成，其中催化剂包含两种过渡金属和/或过渡金属化合物，其中一种存在于氧化步骤中，这两种过渡金属或化合物相互之间相差一个单位，并催化在第二氧化步骤中吸收的自由基脱羧反应，这两种过渡金属或化合物相互之间相差两个单位，并催化C—C键形成反应的双电子过程。
• Highly efficient palladium-catalyzed cross-coupling of diarylborinic acids with arenediazoniums for practical diaryl synthesis
  作者：Fengze Wang、Chen Wang、Guoping Sun、Gang Zou

  DOI：10.1016/j.tetlet.2019.151491

  日期：2020.2

  A highly efficient cross-coupling of cost-effective diarylborinic acids with both isolatable and latent arenediazoniums, i.e. tetrafluoroborates and aryltriazenes, respectively, has been developed with a practical palladium catalyst system under base-free conditions in open flask at room temperature. A variety of electronically and sterically various biaryls, in particular, those bearing a coordinative

  低成本的二芳基硼酸与可分离的和潜在的芳族重氮鎓（即四氟硼酸酯和芳基三氮烯）的高效交叉偶联已在实用的钯催化剂体系下，在无碱条件下于室温下在敞口烧瓶中开发出来。通过使用0.3mol％的乙酸钯作为催化剂，可以以良好或优异的产率获得多种电子和空间上不同的联芳基，特别是那些带有配位邻位取代基的联芳基。该方案的特征包括二芳基硼酸的成本效益，对杂原子邻位取代底物的功效以及对芳基氯化物的高化学选择性，已在杀菌剂Boscalid的实际合成中得到了明确证明。
• Biaryl Synthesis via Pd-Catalyzed Decarboxylative Coupling of Aromatic Carboxylates with Aryl Halides
  作者：Lukas J. Goossen、Nuria Rodríguez、Bettina Melzer、Christophe Linder、Guojun Deng、Laura M. Levy

  DOI：10.1021/ja068993+

  日期：2007.4.1

  with aryl halides. This bimetallic system allows the direct coupling of various aryl, heteroaryl, or vinyl carboxylic acids with aryl or heteroaryl iodides, bromides, or chlorides at 160 degrees C in the presence of a mild base such as potassium carbonate. The present scope and potential economic impact of the reaction are demonstrated by the synthesis of 42 biaryls, some of which are of substantial industrial

  提出了一种用于不对称联芳基区域特异性构建的新策略，其中容易获得的羧酸盐原位脱羧，得到芳基金属物质，在与芳基卤化物的催化交叉偶联反应中充当亲核组分。该催化剂体系由一种铜菲咯啉配合物组成，该配合物介导从芳族羧酸盐中挤出 CO2 以生成芳基铜物种，以及一种钯配合物，该配合物催化这些中间体与芳基卤化物的交叉偶联。这种双金属系统允许各种芳基、杂芳基或乙烯基羧酸与芳基或杂芳基碘化物、溴化物或氯化物在 160 摄氏度下在温和碱（如碳酸钾）存在下直接偶联。42 联芳基化合物的合成证明了该反应的当前范围和潜在的经济影响，其中一些具有重要的工业相关性。讨论了新转型的剩余挑战和未来前景。
• An active catalytic system for Suzuki–Miyaura cross-coupling reactions using low levels of palladium loading
  作者：Meng-Qi Yan、Jia Yuan、Fang Lan、Si-Hao Zeng、Meng-Yue Gao、Sheng-Hua Liu、Jian Chen、Guang-Ao Yu

  DOI：10.1039/c7ob00178a

  日期：——

  An easily available Pd(OAc)2/(2-(anthracen-9-yl)-1H-inden-3-yl) dicyclohexylphosphine/toluene/iPrOH/water catalytic system was developed, which shows high catalytic activity in the Suzuki–Miyaura cross-coupling reactions of a diverse array of aryl and heteroaryl chlorides with Pd loadings down to 0.01 mol%.

  容易获得的Pd（OAC）2 /（2-（蒽-9-基）-1- ħ茚-3-基）二环己基膦/甲苯/我异丙醇/水催化体系被开发，其显示高的催化在铃木活动–Miyaura的各种芳基和杂芳基氯化物的交叉偶联反应，其Pd含量低至0.01 mol％。
• Palladium on Activated Carbon - A Recyclable Catalyst for Suzuki-Miyaura Cross-Coupling of Aryl Chlorides in Water
  作者：Morten Lysén、Klaus Köhler

  DOI：10.1055/s-2006-926305

  日期：——

  Aryl chlorides are efficiently coupled with aryl boronic acids using ligandless Pd/C in water. The catalyst is easily recovered via filtration and reused up to four times with an overall yield of 73%. In addition the catalytic activity and selectivity of a variety of homogeneous and heterogeneous palladium sources have been compared.

  芳基氯化物在水相中使用无配体的Pd/C催化剂能有效地与芳基硼酸进行偶联反应。催化剂通过过滤容易地回收，并可重复使用多达四次，总产率高达73%。此外，比较了多种均相和非均相钯源的催化活性和选择性。