2-(2,6-diphenylphenyl)-2-oxazoline | 851513-83-2

• 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-(2,6-diphenylphenyl)-2-oxazoline
• 英文别名: 2-(2,6-diphenyl)-phenyloxazoline；2-(2,6-Diphenylphenyl)-4,5-dihydro-1,3-oxazole；2-(2,6-diphenylphenyl)-4,5-dihydro-1,3-oxazole
• CAS: 851513-83-2
• 化学式: C₂₁H₁₇NO
• 分子量: 299.372
• InChiKey: AGGKZUMURKKFGJ-UHFFFAOYSA-N

物化性质

• 熔点：
  140.6-141.2 °C
• 沸点：
  493.3±34.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4,5-二氢-2-苯基恶唑 、 四苯硼钠 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer potassium fluoride 、 氯乙酸乙酯 作用下， 以 邻二甲苯 为溶剂， 反应 6.0h， 以71%的产率得到2-(2,6-diphenylphenyl)-2-oxazoline
  参考文献：
  名称：

  Rhodium-catalyzed regioselective arylation of phenylazoles and related compounds with arylboron reagents via C–H bond cleavage

  摘要：

  The rhodium-catalyzed direct ortho-arylation reactions of phenylazoles using arylboron reagents such as tetraarylborates were examined. Ethyl chloroacetate and potassium fluoride were found to effectively act as a hydrogen acceptor and a promoter, respectively, to afford selective formation of the corresponding mono- or diarylated products with good yields. In addition, azobenzene as well as 2-phenylpyridine also underwent the direct arylation under similar conditions. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.04.029

文献信息

• RuCl₃⋅<i>x</i> H₂O-Catalyzed Direct Arylation of Arenes with Aryl Chlorides in the Presence of Triphenylphosphine
  作者：Ning Luo、Zhengkun Yu

  DOI：10.1002/chem.200902612

  日期：2010.1.18

  A simple, efficient, and economically attractive catalytic system has been developed for the direct arylation of arenes with aryl chlorides with the RuCl3⋅xH2O/PPh3/Na2CO3/N‐methyl‐2‐pyrrolidone system (see scheme). A remarkable effect of the nature of the base was observed, with Na2CO3 giving the best results.

  一个简单的，高效和经济上有吸引力的催化体系已被开发用于芳烃的与和的RuCl芳基氯的直接芳基化3 ⋅ X ħ 2 O / PPH 3 /钠2 CO 3 / Ñ甲基-2-吡咯烷酮系统（参见方案）。观察到了碱性质的显着影响，其中Na 2 CO 3给出了最佳结果。
• Rhodium/N-Heterocyclic Carbene Catalyzed Direct Intermolecular Arylation of sp²and sp³CH Bonds with Chelation Assistance
  作者：Min Kim、Jaesung Kwak、Sukbok Chang

  DOI：10.1002/anie.200903500

  日期：2009.11.9

  chelation‐assisted direct intermolecular arylation using an N‐heterocyclic carbene and phosphine ligands (see scheme; IMes=1,3‐bis(2,4,6‐trimethylphenyl)imidazol‐2‐ylidene). The reaction is operationally simple, proceeds under mild reaction conditions to afford mono‐ or diarylated products in excellent yields, and is applicable to the arylation at the sp3 or sp2 CH bonds of 2‐pyridyl‐containing aryl, vinyl

  Rh-oadies加入：使用N-杂环卡宾和膦配体（见方案; IMes = 1,3-双（2,4,6-三甲基苯基）咪唑）开发了一种新的铑催化剂，用于螯合辅助的直接分子间芳基化-2-亚基）。该反应操作简单，在温和的反应条件下进行，得到单或diarylated产品以优良产率，并且适用于在SP的芳基化3或sp 2 ç 的含有2-吡啶基-芳基，乙烯基H键，或烷基部分。
• Diethyl carbonate as a solvent for ruthenium catalysed C–H bond functionalisation
  作者：Percia Arockiam、Valentin Poirier、Cédric Fischmeister、Christian Bruneau、Pierre H. Dixneuf

  DOI：10.1039/b913115a

  日期：——

  The ruthenium catalysed direct functionalisation of arene C–H bonds by aryl halides is reported. Reactions were performed in diethyl carbonate (DEC) instead of N-methylpyrrolidone (NMP), the solvent of choice used in most ruthenium catalysed C–H bond transformations. The use of diethyl carbonate facilitates the workup procedure thus reducing the amount of waste water. The slight loss of activity due to the use of diethyl carbonate is counterbalanced by the improvement of the catalyst efficiency achieved by a judicious choice of additives. Several arenes containing an N-heterocycle as a directing group have been diarylated.

  本报告介绍了芳基卤化物在钌催化下对炔烃 CâH 键的直接官能化。反应是在碳酸二乙酯（DEC）而非 N-甲基吡咯烷酮（NMP）中进行的，后者是大多数钌催化 CâH 键转化反应的首选溶剂。使用碳酸二乙酯简化了加工程序，从而减少了废水量。使用碳酸二乙酯会导致活性略有下降，但通过合理选择添加剂，催化剂的效率会得到提高，从而抵消了活性的下降。几种含有 N-杂环作为指导基团的烷烃已被二芳基化。
• C–H bond functionalisation with [RuH(codyl)2]BF4 catalyst precursor
  作者：Wenbo Li、Percia B. Arockiam、Cedric Fischmeister、Christian Bruneau、Pierre H. Dixneuf

  DOI：10.1039/c1gc15642j

  日期：——

  Direct catalytic diarylation with (hetero)arylhalides of arenes containing an heterocycle (pyridine, oxazoline, pyrazole) has been performed with a ruthenium catalyst assisted by a coordinating base. It constitutes a green process for cross-coupled C–C bond formation without any metal salt waste. The new catalytic system is based on [HRu(codyl)2]BF4/2KY (KY: KOAc, KOPiv, KPI (potassium phtalimide)] in which the assisting ligand Y promotes the initial cleavage of C–H bonds. It is shown that the efficiency of the Ru/2KY system strongly depends on the nature of both substrates.

  在配位碱的辅助下，利用钌催化剂对含有杂环（吡啶、噁唑啉、吡唑）的炔烃的（杂）芳基卤化物进行了直接催化二芳基化反应。这是一种不产生任何金属盐废物的交叉耦合 CâC 键形成的绿色工艺。新催化体系基于[HRu(codyl)2]BF4/2KY（KY：KOAc、KOPiv、KPI（磷酰亚胺钾）]，其中辅助配体 Y 可促进 CâH 键的初始裂解。研究表明，Ru/2KY 系统的效率在很大程度上取决于两种底物的性质。
• Nitrogen-directed ortho-arylation and -heteroarylation of aromatic rings catalyzed by ruthenium complexes
  作者：Shuichi Oi、Raito Funayama、Tetsutaro Hattori、Yoshio Inoue

  DOI：10.1016/j.tet.2007.12.060

  日期：2008.6

  The ruthenium-catalyzed direct ortho-arylation reactions of 2-phenylpyridine and 2-aryloxazolines have been successfully expanded to the direct aryl–heteroaryl coupling reactions using heteroaryl bromides. The reaction mechanism involving the RuII/RuIV intermediates is proposed from the results of the stoichiometric reaction of a divalent ruthenacycle complex of 2-phenylpyridine with bromobenzene.

  钌催化的2-苯基吡啶和2-芳基恶唑啉的直接邻芳基化反应已成功扩展为使用杂芳基溴化物的直接芳基-杂芳基偶联反应。从2-苯基吡啶与溴苯的二价钌循环络合物的化学计量反应结果，提出了涉及Ru II / Ru IV中间体的反应机理。