[2,6-2H2]-4-phenylbenzoic acid

• 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: [2,6-2H2]-4-phenylbenzoic acid
• 英文别名: 2,6-Dideuterio-4-phenylbenzoic acid
• 化学式: C₁₃H₁₀O₂
• 分子量: 200.205
• InChiKey: NNJMFJSKMRYHSR-XETGXLELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• 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

• 作为产物：
  描述：

  4-苯基苯甲酸 在 重水 、 palladium diacetate 、 silver trifluoroacetate 、 三氟乙酸 作用下， 以45 %的产率得到[2,6-2H2]-4-phenylbenzoic acid
  参考文献：
  名称：

  Palladium-Catalyzed Ligand-Free ortho-Deuteration of Aromatic Carboxylic Acids with D2O

  摘要：

  摘要：本文开发了一种无配体、钯催化的芳香羧酸正位氘代反应，使用D2O作为氘源。与它们的间位取代类似物相比，对于邻位和对位取代苯甲酸的氢同位素交换，观察到了异常低的反应性。进一步研究揭示了反应温度是反应性的关键参数，改良条件可以获得具有良好至优异氘化程度的氘代产物。

  DOI：

  10.1055/a-1859-8012

文献信息

• Ruthenium(<scp>ii</scp>)-catalyzed C–H functionalizations on benzoic acids with aryl, alkenyl and alkynyl halides by weak-O-coordination
  作者：Ruhuai Mei、Cuiju Zhu、Lutz Ackermann

  DOI：10.1039/c6cc07773k

  日期：——

  C-H arylations of weakly coordinating benzoic acids were achieved by versatile ruthenium(II) catalysis with ample substrate scope. Thus, user-friendly ruthenium(II) biscarboxylate complexes modified with tricyclohexylphosphine enabled C-H functionalizations with aryl...

  弱配位的苯甲酸的CH芳基化反应是通过通用的钌（II）催化并在足够的底物范围内实现的。因此，使用三环己基膦修饰的用户友好型钌（II）双羧酸钌（II）配合物可实现芳基的CH功能化。
• Parallel chemistry investigations of ortho-directed hydrogen isotope exchange between substituted aromatics and isotopic water: novel catalysis by cyclooctadienyliridium(I)pentan-1,3-dionates
  作者：Lee P Kingston、William J.S Lockley、Andrew N Mather、Edward Spink、Stewart P Thompson、David J Wilkinson

  DOI：10.1016/s0040-4039(00)00244-6

  日期：2000.4

  Novel iridium-based catalysts which promote ortho-directed hydrogen isotope exchange between substituted aromatics and isotopic water have been identified via a combination of screening and subsequent ligand optimisation. The catalysts are more active, operate at lower temperature and are applicable to a wider variety of substrates than previously known systems.

  促进新的基于铱的催化剂邻取代的芳族化合物和水的同位素之间-directed氢同位素交换已经通过筛选的组合，并且随后的优化配体识别。与先前已知的系统相比，该催化剂更具活性，可在较低的温度下操作，并且可用于多种底物。
• Convenient and efficient deuteration of functionalized aromatics with deuterium oxide: catalysis by cycloocta-1,5-dienyliridium(I) 1,3-dionates
  作者：B. McAuley、M. J. Hickey、L. P. Kingston、J. R. Jones、W. J. S. Lockley、A. N. Mather、E. Spink、S. P. Thompson、D. J. Wilkinson

  DOI：10.1002/jlcr.780

  日期：2003.11

  Aromatic compounds bearing an ortho-directing substituent may be deuterated by exchange with deuterium oxide in the presence of a range of cycloocta-1,5-dienyliridium(I)1,3-dionate catalysts. The exchange takes place in several dipolar aprotic solvents and is directly applicable to the deuteration of polar compounds. Isotope incorporation is efficient and regiospecific. The method is applicable to a wide range of ortho-directing groups some of which are only weak directors for alternative ortho-labelling approaches. In addition, the application of microwaves enables labelling within minutes even with sub-stituents which are poor directors. Copyright © 2003 John Wiley & Sons, Ltd.

  具有邻位导向取代基的芳香化合物可在多种环辛二烯基铱(I)1,3-二酮催化剂的存在下，通过与重水交换实现氘代。该交换过程可在多种偶极非质子溶剂中进行，并可直接应用于极性化合物的氘代。同位素掺入效率高且区域选择性强。该方法适用于多种邻位导向基团，其中一些基团对于其他邻位标记方法仅具有较弱的导向作用。此外，微波的应用使得即使对于导向作用较弱的取代基，也能在几分钟内完成标记。版权所有 © 2003 John Wiley & Sons, Ltd.
• Palladium-Catalyzed Ligand-Free ortho-Deuteration of Aromatic Carboxylic Acids with D2O
  作者：Ziyin Zhang、Zhi-Jiang Jiang、Jia Chen、Yiwei Cao、Zhanghua Gao

  DOI：10.1055/a-1859-8012

  日期：2022.11

  A ligand-free, palladium-catalyzed ortho-deuteration of aromatic carboxylic acids was developed using D2O as the deuterium source. Compared to their meta-substituted analogues, an unusually lower reactivity in para- and ortho-substituted benzoic acids toward hydrogen isotope exchange was observed. Further investigation revealed that the reaction temperature is a critical parameter for the reactivity, and the modified conditions can afford deuterated products with good to excellent deuterium incorporation.

  摘要：本文开发了一种无配体、钯催化的芳香羧酸正位氘代反应，使用D2O作为氘源。与它们的间位取代类似物相比，对于邻位和对位取代苯甲酸的氢同位素交换，观察到了异常低的反应性。进一步研究揭示了反应温度是反应性的关键参数，改良条件可以获得具有良好至优异氘化程度的氘代产物。