4-methyl-N-(2-(pyridin-2-yl)ethyl)benzenesulfonamide | 84119-88-0

• 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: 4-methyl-N-(2-(pyridin-2-yl)ethyl)benzenesulfonamide
• 英文别名: 4-methyl-N-(2-pyridin-2-ylethyl)benzenesulfonamide
• CAS: 84119-88-0
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: RDNCVSUGRNJACC-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C(Solv: ethanol (64-17-5))
• 沸点：
  442.1±55.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(2-(pyridin-2-yl)ethyl)benzenesulfonamide 、 bis[dichloro(pentamethylcyclopentadienyl)iridium(III)] 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到pentamethylcyclopentadienyl(iridium(4-methyl-N-(2-(pyridin-2-yl)ethyl)benzenesulfonamide))chloride
  参考文献：
  名称：

  使用Cp * Ir（吡啶磺酰胺）Cl预催化剂对酮进行无碱转移加氢

  摘要：

  N-(2-(Pyridin-2-yl)ethyl)benzenesulfonamide derivatives and 1,1,1-trifluoro-N-(2-(pyridin-2-yl)ethyl)methanesulfonamide (1-4), along cat. with three-legged piano stool Cp*(IrCl)-Cl-III complexes (5-11) (Cp* = pentamethylcyclopentadienyl) bearing pyridinesulfonamide ligands with varying electronic parameters, were synthesized. These ligands and air-stable complexes were characterized by H-1 and C-13{H-1} NMR spectroscopy, elemental analysis, and single-crystal X-ray diffraction. Precatalysts, 5-11, were assessed for transfer hydrogenation of aryl, diaryl, dialkyl, linear, cycloaliphatic, and alpha,beta-unsaturated ketones, diones, beta-ketoesters, and a biomass-derived substrate with 2-propanol, using 1 mol % precatalyst. Catalysis was also efficient using a 0.1 mol % loading. Remarkably, all catalysis experiments can be conducted in air without dried and degassed substrates, and basic additives and halide abstractors are not required for high activity in transfer hydrogenation. Control experiments and a mercury poisoning experiment support a homogeneous catalyzed pathway. Overall, the fastest reactions are observed using electron-poor substrates and precatalysts bearing electron-rich ligands.

  DOI：

  10.1021/acs.organomet.5b00864
• 作为产物：
  描述：

  2-乙烯基吡啶 、 对甲苯磺酰胺 在 silver hexafluoroantimonate 、 1,2-双(二苯基膦)乙烷 、 copper(ll) bromide 作用下， 以 1,1,2,2-四氯乙烷 为溶剂， 反应 20.0h， 以16%的产率得到4-methyl-N-(2-(pyridin-2-yl)ethyl)benzenesulfonamide
  参考文献：
  名称：

  铜盐和银盐的组合催化未活化烯烃的分子间和分子内加氢胺化：Brønstedt酸催化的展开

  摘要：

  卤化铜，银盐和膦配体的组合使用被用于催化烯烃的分子间和分子内加氢胺化。研究了未活化烯烃与氮底物的反应。机理研究表明，该催化体系产生了布朗斯台德酸，该酸似乎是主要的催化物种。

  DOI：

  10.1002/adsc.201000536

文献信息

• Ligand-Free Copper(I)-Catalyzed Benzylic Acyloxylation of 2-Alkylpyridines under Aerobic Conditions
  作者：Li Cheng、Yuqian Sun、Wenrong Wang、Changsheng Yao、Tuan-Jie Li

  DOI：10.1021/acs.joc.8b02794

  日期：2019.3.15

  A ligand-free copper(I)-catalyzed benzylic acyloxylation of 2-alkylpyridines with carboxylic acids was realized by using 1.0 atm of O2 as a green oxidant. The transformation provided a facile access to a wide range of N-heterocyclic esters through C–O bond formation, with broad substrate scope and good functional group tolerance. Preliminary mechanistic investigations showed that this protocol included

  通过使用1.0 atm的O 2作为绿色氧化剂，实现了无配体的铜（I）催化2-烷基吡啶与羧酸的苄基酰氧基化反应。这种转变通过形成C–O键，提供了广泛的N-杂环酯的便捷途径，具有广泛的底物范围和良好的官能团耐受性。初步的机械研究表明，该协议包括一个基本过程。
• Electrochemical C−H Amidation of Heteroarenes with<i>N</i>‐Alkyl Sulfonamides in Aqueous Medium
  作者：Yan Zhang、Zhipeng Lin、Lutz Ackermann

  DOI：10.1002/chem.202004229

  日期：2021.1.4

  The construction of C−N bonds by free radical reactions represents a powerful synthetic approach for direct C−H amidations of arenes or heteroarenes. Developing efficient and more environmentally friendly synthetic methods for C−H amidation reactions remains highly desirable. Herein, metal‐free electrochemical oxidative dehydrogenative C−H amidations of heteroarenes with N‐alkylsulfonamides have been

  通过自由基反应构建C-N键代表了对芳烃或杂芳烃直接C-H酰胺化的强大合成方法。为CH酰胺化反应开发高效且对环境友好的合成方法仍然是非常可取的。在此，杂芳烃与N-烷基磺酰胺的无金属电化学氧化脱氢CHH酰胺化反应已经完成。不含催化剂和化学氧化剂的CHH酰胺化反应范围广，并使用电作为绿色和唯一的氧化剂。各种杂芳烃，包括吲哚，吡咯，苯并呋喃和苯并噻吩，都经过了这种C（sp 2）-H氮化。循环伏安法研究和控制实验为无金属电催化直接生成以氮为中心的自由基提供了证据。
• Cycloauration of pyridyl sulfonamides
  作者：Kelly J. Kilpin、William Henderson、Brian K. Nicholson

  DOI：10.1039/b803835j

  日期：——

  The pyridyl-2-alkylsulfonamides C5H4N(CH2)nNHSO2R (n = 1,2; R = Me, Ph or p-C6H4Me) and 8-(p-tosylamino)quinoline undergo facile cycloauration reactions with H[AuCl4] in water, giving metallacyclic complexes coordinated through the pyridyl (or quinolyl) nitrogen atom and the deprotonated nitrogen of the sulfonamide group. The complexes have been fully characterised by NMR spectroscopy, ESI mass spectrometry and elemental analysis. The X-ray crystal structures of two derivatives reveal the presence of non-planar sulfonamide nitrogen atoms. The complexes show low activity against P388 murine leukaemia cells, possibly as a result of their ease of reduction with mild reducing agents.

  吡啶-2-烷基磺酰胺C5H4N(CH2)nNHSO2R（n=1,2；R=Me，Ph或对甲苯基）和8-（对甲苯磺酰胺基）喹啉在水中与H[AuCl4]发生易行的环金化反应，生成通过吡啶（或喹啉）氮原子和磺酰胺基团的脱质子氮原子配位的金属环状配合物。这些配合物通过NMR光谱、ESI质谱和元素分析得到了充分表征。两个衍生物的X射线晶体结构揭示了非平面硫酰胺氮原子的存在。这些配合物对P388小鼠白血病细胞的活性较低，可能是由于它们易于被温和的还原剂还原的结果。
• MODULATORS OF ATP-BINDING CASSETTE-TRANSPORTERS
  申请人：HADIDA RUAH SARA S.

  公开号：US20090143381A1

  公开（公告）日：2009-06-04

  Compounds of the present invention, and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (“ABC”) transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (“CFTR”). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.

  本发明的化合物及其药用可接受的组合物可用作ATP结合盒（“ABC”）转运蛋白或其片段的调节剂，包括囊性纤维化跨膜传导调节蛋白（“CFTR”）。本发明还涉及使用本发明的化合物治疗ABC转运蛋白介导的疾病的方法。
• Synthesis and Some First-Row Transition-Metal Complexes of the 1,2,4-Triazole-Based Bis(terdentate) Ligands TsPMAT and PMAT
  作者：Marco H. Klingele、Boujemaa Moubaraki、Keith S. Murray、Sally Brooker

  DOI：10.1002/chem.200500387

  日期：2005.11.18

  octahedral, as evidenced by the X-ray crystal structure analyses of [Co(II) (2)(TsPMAT)(2)](BF(4))(4)6 MeCN (246 MeCN) and [Fe(II) 2(PMAT)2](BF4)4DMF (27DMF). Studies of the magnetic properties of [Co(II) 2(TsPMAT)2](BF4)4.4 H2O (244 H2O), [Mn(II) 2(PMAT)2](ClO4)4 (26), and [Co(II) 2(PMAT)2](BF4)4 (28) have revealed weak antiferromagnetic coupling (J=-3.3, -0.16, and -2.4 cm(-1), respectively) between the two

  已经研究了采用基于亲核取代而不是席夫碱缩合的策略来制备1,2,4-三唑基配体，并导致了两种新配体的合成，即4-氨基-3， 5-双[N-（2-吡啶基甲基）-N-（4-甲苯磺酰基）氨基]甲基} -4H-1,2,4-三唑（TsPMAT，14）和4-氨基-3,5-bis [（2-吡啶基甲基）氨基]甲基} -4H-1,2,4-三唑（PMAT，15）。这些是掺入1,2,4-三唑单元的双（齿）配体的第一个实例。TsPMAT（14）与Co（BF4）2.6 H2O形成双核2：2络合物，即使当金属与配体的摩尔比为2：1时也是如此。同样，PMAT（15）与Mn（ClO4）2.6 或M（ ）2.6 （M = Fe，Co，Ni，Zn）配体与金属的摩尔比为1：1的反应提供了通式[M（II）（2）（PMAT）2] X4的一系列配合物。TsPMAT（14）和PMAT（15）的这些络合物中的金属中心被两个配体分子包裹，并被1