[2',6'-2H2]-benzenesulfonamide

• 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]-benzenesulfonamide
• 英文别名: 2,6-Dideuteriobenzenesulfonamide；2,6-dideuteriobenzenesulfonamide
• 化学式: C₆H₇NO₂S
• 分子量: 159.177
• InChiKey: KHBQMWCZKVMBLN-KFRNQKGQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯磺酰胺 在 吡啶 silver tetrafluoroborate 、 bis(1,5-cyclooctadiene)diiridium(I) dichloride 、 氘 作用下， 以 二氯甲烷 为溶剂， 以8 mg的产率得到[2',6'-2H2]-benzenesulfonamide
  参考文献：
  名称：

  原位形成的铱配合物介导的氘交换条件

  摘要：

  已经筛选了一系列原位形成的铱基络合物，其在一系列模型底物中介导氢的邻位交换，所述铱基络合物包含吡啶，膦，三苯基ar，三苯基stibine和三苯胺作为配体。已经实现了将其并入许多基材类别中的改进。在金属中心的电子性质和配体数量有助于确定哪种催化剂最适合在任何给定的底物中进行交换。

  DOI：

  10.1016/s0040-4020(03)00422-8

文献信息

• Iridium-Catalyzed C–H Activation and Deuteration of Primary Sulfonamides: An Experimental and Computational Study
  作者：William J. Kerr、Marc Reid、Tell Tuttle

  DOI：10.1021/cs5015755

  日期：2015.1.2

  Iridium-catalyzed C-H activation and ortho-hydrogen isotope exchange is an important technology for allowing access to labelled organic substrates and aromatic drug molecules, and for the development of further C-H activation processes in organic synthesis. The use of [(COD)Ir(NHC)Cl] complexes (NHC = N-heterocyclic carbene) in the ortho-deuteration of primary sulfonamides under ambient conditions is reported. This methodology has been applied to the deuteration of a series of substrates, including the COX-2 inhibitors Celecoxib and Mavacoxib, demonstrating selective complexation of the primary sulfonamide over a competing pyrazole moiety. The observed chemoselectivity can be reversed by employing more encumbered catalyst derivatives of the type [(COD)Ir(NHC)(PPh3)]PF6. Computational studies have revealed that, although C-H activation is rate-determining, substrate complexation or subsequent C-H activation can be product-determining depending on the catalyst employed.
• Isotopic Labelling of Functionalised Arenes Catalysed by Iridium(I) Species of the [(cod)Ir(NHC)(py)]PF6 Complex Class
  作者：William Kerr、Paul Cross、John Herbert、Alan McNeill、Laura Paterson

  DOI：10.1055/s-0035-1560518

  日期：——

  Iridium(I) complexes of the type [(cod)Ir(NHC)(Py)]PF6 have been exposed as efficient catalysts in the area of hydrogen-isotope exchange. More specifically, by an ortho-directed C-H activation process, high levels of deuterium incorporation have been achieved using low levels of catalyst over a range of functionalised aromatic compounds. Additionally, the developed protocol has been extended to include a selected pharmacological target, where chemoselective labelling is observed within such a multifunctional substrate.