1,3-Dideuterio-2-nitrobenzene | 142207-34-9

• 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: 1,3-Dideuterio-2-nitrobenzene
• 英文别名: 1,3-dideuterio-2-nitrobenzene
• CAS: 142207-34-9
• 化学式: C₆H₅NO₂
• 分子量: 125.095
• InChiKey: LQNUZADURLCDLV-KFRNQKGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  硝基苯 在 [(COD)Ir(PPh₃)(1,3-bis(mesityl)imidazolin-2-ylidene)][PF₆] 氘 作用下， 以 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以98%的产率得到1,3-Dideuterio-2-nitrobenzene
  参考文献：
  名称：

  高活性铱（I）配合物，用于催化氢同位素交换。

  摘要：

  已经开发出了用于制备具有庞大的N-杂环卡宾和膦配体的新型铱配合物的实用方便的方法。这些常规处理的配合物是定向氢同位素交换过程中的高活性催化剂。

  DOI：

  10.1039/b715938b

文献信息

• Iridium-Catalyzed H/D Exchange: Ligand Complexes with Improved Efficiency and Scope
  作者：Michael Parmentier、Thomas Hartung、Andreas Pfaltz、Dieter Muri

  DOI：10.1002/chem.201402078

  日期：2014.9.1

  could be labeled efficiently. With the addition of tris(pentafluorophenyl) borane to the reaction mixture, also highly deactivating nitrile substituents were well tolerated in the reaction. Based on the excellent results obtained with the chiral ThrePhox ligand, a structurally simpler, achiral ligand was developed. The iridium complex containing this ligand, proved to be a powerful catalyst for HIE reactions

  氢同位素交换（HIE）是将氘或tri引入有机化合物的最有吸引力的工具之一。在此，已对具有N，P-配体的铱络合物（用于不对称双键还原的高活性催化剂）的HIE功能进行了测试。含有二环己基膦或次膦酸酯的富电子配体被认为是有效掺入氘的优异配体。具有强指导基团（即吡啶，酮和酰胺）以及弱连接单元（如硝基，砜和磺酰胺）的底物可以得到有效标记。通过向反应混合物中加入三（五氟苯基）硼烷，在反应中也很好地耐受了高度失活的腈取代基。基于使用手性ThrePhox配体获得的优异结果，开发了结构更简单的非手性配体。含有该配体的铱络合物被证明是HIE反应的有力催化剂。
• Hydrogen isotope exchange with highly active iridium(I) NHC/phosphine complexes: a comparative counterion study
  作者：William J. Kerr、Richard J. Mudd、Philippa K. Owens、Marc Reid、Jack A. Brown、Sebastien Campos

  DOI：10.1002/jlcr.3427

  日期：2016.12

  present a range of substrates that undergo hydrogen isotope exchange with an iridium(I) N-heterocyclic carbene/phosphine complex bearing the less coordinating tetrakis[3,5-bis(trifluoromethyl)phenyl]borate counterion and compare these with labelling using the equivalent, more established hexafluorophosphate complex. The changes in reactivity and selectivity of these complexes in a series of solvents

  在此，我们提出了一系列与铱（I）N-杂环卡宾/膦配合物进行氢同位素交换的底物，该配合物带有较少配位的四[3,5-双（三氟甲基）苯基]硼酸平衡离子，并将这些与标记进行比较等效的、更成熟的六氟磷酸盐复合物。检查了这些配合物在一系列溶剂中的反应性和选择性的变化。版权所有 © 2016 John Wiley & Sons, Ltd.
• Burgess iridium(I)-catalyst for selective hydrogen isotope exchange
  作者：Annina Burhop、Raphail Prohaska、Remo Weck、Jens Atzrodt、Volker Derdau

  DOI：10.1002/jlcr.3512

  日期：2017.6.15

  commercially available Burgess catalyst in hydrogen isotope exchange reactions with several substrates bearing different directing group functionalities and have obtained moderate to high (50%-97%D) deuterium incorporations. The broad applicability in hydrogen isotope exchange reactions makes the Burgess catalyst a possible alternative compared to other commercially available iridium(I)-catalysts.

  我们评估了市售的 Burgess 催化剂在氢同位素交换反应中与几种具有不同导向基团官能团的底物，并获得了中等至高 (50%-97%D) 的氘掺入。与其他市售铱 (I) 催化剂相比，Burgess 催化剂在氢同位素交换反应中的广泛适用性使之成为可能的替代品。
• 一种氘代芳香硝基类化合物的制备方法
  申请人：浙大宁波理工学院

  公开号：CN114315589A

  公开（公告）日：2022-04-12

  本发明公开了一种氘代芳香硝基类化合物的制备方法，以式Ⅰ所示的芳香硝基衍生物为原料，在惰性气氛保护下，经催化体系作用与氘源试剂发生氘代反应，反应产物经过分离提纯而得；所述催化体系包括银催化剂、配体、溶剂和缚酸剂。本发明工艺方法普适性好，可用于多种芳香硝基衍生物氘代产物的制备；具有安全、绿色、廉价的特点。
• The Synthesis of Highly Active Iridium(I) Complexes and their Application in Catalytic Hydrogen Isotope Exchange
  作者：Jack A. Brown、Alison R. Cochrane、Stephanie Irvine、William J. Kerr、Bhaskar Mondal、John A. Parkinson、Laura C. Paterson、Marc Reid、Tell Tuttle、Shalini Andersson、Göran N. Nilsson

  DOI：10.1002/adsc.201400730

  日期：2014.11.24

  AbstractA series of robust iridium(I) complexes bearing a sterically encumbered N‐heterocyclic carbene ligand, alongside a phosphine ligand, has been synthesised and investigated in hydrogen isotope exchange processes. These complexes have allowed isotope incorporation over a range of substrates with the use of practically convenient deuterium and tritium gas. Moreover, these active catalysts are capable of isotope incorporation to particularly high levels, whilst employing low catalyst loadings and in short reaction times. In addition to this, these new catalyst species have shown flexible levels of chemoselectivity, which can be altered by simple manipulation of preparative approaches. Furthermore, a number of industrially‐relevant drug molecules has also been labelled, including the sulfonamide containing drug, Celecoxib. Alongside detailed NMR experiments, initial mechanistic investigations have also been performed, providing insight into both substrate binding energies, and, more importantly, relative energies of key steps in the mechanistic cycle as part of the overall exchange process.magnified image