[1,1':3',1'']三联苯-2'-羧酸 | 5547-35-3

• 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: [1,1':3',1'']三联苯-2'-羧酸
• 英文名称: 2,6-diphenylbenzoic acid
• 英文别名: [1,1':3',1''-terphenyl]-2'-carboxylic acid；m-Terphenyl-2'-carbonsaeure
• CAS: 5547-35-3
• 化学式: C₁₉H₁₄O₂
• 分子量: 274.319
• InChiKey: UKJFDHQIVVKJTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  [1,1':3',1'']三联苯-2'-羧酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 [1,1':3',1''-terphenyl]-2'-carbonyl chloride
  参考文献：
  名称：

  A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes

  摘要：

  A new primary amine catalyst for the asymmetric a-hydroxylation and a-fluorination of alpha-branched aldehydes is described. The products of the title transformations are generated in excellent yields with high enantioselectivities. Both processes can be performed within short reaction times and on gram scale. The similarity in results obtained in both reactions, combined with computational evidence, implies a common basis for stereoinduction and the possibility of a general catalytic mechanism for a-functionalizations. Promising initial results in alpha-amination and alpha-chlorination reactions support this hypothesis.

  DOI：

  10.1021/acs.orglett.5b01193
• 作为产物：
  描述：

  苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 水 、 sodium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 6.0h， 生成 [1,1':3',1'']三联苯-2'-羧酸
  参考文献：
  名称：

  Silver-Catalyzed C(sp²)–H Functionalization/C–O Cyclization Reaction at Room Temperature

  摘要：

  Silver-catalyzed C(sp(2))-H functionalization/CO cyclization has been developed. The scalable reaction proceeds at room temperature in an open flask. The present method exhibits good functional-group compatibility because of the mild reaction conditions. Using a AgNO3 catalyst and a (NH4)(2)S2O8 oxidant in CH2Cl2/H2O solvent, various lactones are obtained in good to excellent yields. A kinetic isotope effect (KIE) study indicates that the reaction may occur via a radical process.

  DOI：

  10.1021/jo5024238

文献信息

• RuH2(CO)(PPh3)3-catalyzed arylation of aromatic esters using arylboronates via C–H bond cleavages
  作者：Kentaroh Kitazawa、Masashi Kotani、Takuya Kochi、Michael Langeloth、Fumitoshi Kakiuchi

  DOI：10.1016/j.jorganchem.2010.01.022

  日期：2010.4

  The RuH2(CO)(PPh3)3-catalyzed C–H functionalization of aromatic esters with 5,5-dimethyl-2-aryl-[1,3,2]dioxaborinanes (arylboronates) gave the ortho arylation products. This coupling reaction can be performed with various combinations of isopropyl benzoate derivatives and arylboronates. Introduction of CF3 group in the aromatic ring increased the reactivity of the esters. Pinacolone effectively served

  RuH 2（CO）（PPh 3）3催化的芳香族酯与5,5-二甲基-2-芳基-[1,3,2]二氧杂硼烷酮（芳基硼酸酯）的C–H官能化反应得到邻芳基化产物。该偶联反应可以用异丙基苯甲酸酯衍生物和芳基硼​​酸酯的各种组合进行。在芳环中引入CF 3基团增加了酯的反应性。Pinacolone有效地充当了由C–H键断裂产生的氢化物的接受体，并且使用的pinacolone的量也影响了芳基化产物的收率。
• Fe(III)-catalyzed oxidative coupling of alkylnitriles with aromatic carboxylic acids: Facile access to cyanomethyl esters
  作者：Dan Wang、Bing Lu、Yan-Ling Song、Hong-Mei Sun、Qi Shen

  DOI：10.1016/j.tetlet.2019.150969

  日期：2019.8

  The first oxidative coupling of alkylnitriles with aromatic carboxylic acids using di-tert-butyl peroxide (DTBP) as oxidant was achieved under the catalysis of ionic Fe(III) complexes bearing an imidazolinium cation. This protocol features nontoxic iron catalysis, direct α-C(sp3)–H bond oxidative esterification of alkylnitriles, non-prefunctionalized starting materials, and a broad substrate scope

  在带有咪唑啉阳离子的离子化Fe（III）配合物的催化下，使用过氧化二叔丁基（DTBP）作为氧化剂，将烷基腈与芳香族羧酸进行了首次氧化偶联。该方案具有无毒铁催化，烷基腈的直接α-C（sp 3）–H键氧化酯化反应，非预功能化的起始原料以及广泛的底物范围和出色的位阻耐受性，从而提供了一种新颖，直接且绿色的方法氰基甲基酯的合成。
• USE OF ARYL CHLORIDES IN PALLADIUM-CATALYZED C-H BOND FUNCTIONALIZATION
  申请人：Daugulis Olafs

  公开号：US20090012293A1

  公开（公告）日：2009-01-08

  A one-step method for efficiently converting carbon-hydrogen bonds into carbon-carbon bonds using chloroarenes and palladium catalysts is disclosed. This method allows faster introduction of complex molecular entities, a process that would otherwise require many more steps. This invention is particularly relevant for the organic synthesis of complex molecules such as, but not limited to, pharmacophores.

  一种将氯代芳烃和钯催化剂高效地将碳氢键转化为碳碳键的一步法方法被揭示。该方法可以更快地引入复杂的分子实体，而这个过程通常需要更多的步骤。这一发明特别适用于有机合成复杂分子，例如但不限于药用分子。
• Two Methods for Direct <i>ortho</i>-Arylation of Benzoic Acids
  作者：Hendrich A. Chiong、Quynh-Nhu Pham、Olafs Daugulis

  DOI：10.1021/ja071845e

  日期：2007.8.1

  of free benzoic acids have been developed. The first method employs stoichiometric silver acetate for iodide removal, aryl iodide as the coupling partner, and acetic acid solvent. This method is applicable to the arylation of electron-rich to moderately electron-poor benzoic acids and tolerates chloride and bromide substituents on both coupling partners. The second method involves the use of aryl chloride

  已经开发了两种新的钯催化方法，用于游离苯甲酸的直接邻位芳基化。第一种方法使用化学计量的乙酸银去除碘化物，芳基碘化物作为偶联伙伴，以及乙酸溶剂。该方法适用于富电子到中度缺电子苯甲酸的芳基化，并且在两个偶联伙伴上都可以耐受氯化物和溴化物取代基。第二种方法涉及使用芳基氯、碳酸铯碱、正丁基-二-1-金刚烷基膦配体和 DMF 溶剂，适用于富电子和缺电子苯甲酸。第二种方法的机理研究表明异裂 CH 键裂解是速率决定步骤。
• The Expedient and Regioselective Metalation of Unprotected Biphenyl-2-, -3-, and -4-carboxylic Acids
  作者：David Tilly、Subhendu S. Samanta、Anne-Sophie Castanet、Asish De、Jacques Mortier

  DOI：10.1002/ejoc.200500469

  日期：2006.1

  subjected to site-selective electrophilic substitution. The remote C2′-position is attacked by the superbasic mixture of n-butyllithium and potassium tert-butoxide (LICKOR, 3.5 equiv.) in THF or benzene at 20–60 °C. The resulting dianion cyclizes to give the fluorenone skeleton. The metalation reactions of biphenyl-3- and -4-carboxylic acids are also described. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim

  未保护的联苯-2-羧酸可以在与羧酸盐相邻的位置用仲丁基锂完全金属化，然后可以进行位点选择性亲电取代。在 20–60 °C 的 THF 或苯中，正丁基锂和叔丁醇钾（LICKOR，3.5 当量）的超碱性混合物会攻击远程 C2' 位。所得二价阴离子环化得到芴酮骨架。还描述了联苯-3-和-4-羧酸的金属化反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)