N-methyl-N-3-pyridyl-p-toluenesulfonamide | 100795-50-4

• 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: N-methyl-N-3-pyridyl-p-toluenesulfonamide
• 英文别名: N,4-dimethyl-N-pyridin-3-ylbenzenesulfonamide
• CAS: 100795-50-4
• 化学式: C₁₃H₁₄N₂O₂S
• 分子量: 262.332
• InChiKey: SPDYKYUOKZTWRY-UHFFFAOYSA-N

物化性质

• 沸点：
  412.8±47.0 °C(Predicted)
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-methyl-N-3-pyridyl-p-toluenesulfonamide 在 硫酸 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 1.0h， 生成 N,N',N''-trimethyl-N,N',N''-tris(3-pyridyl)-1,3,5-benzene tricarboxamide
  参考文献：
  名称：

  A new prearranged tripodant ligand N,N′,N″-trimethyl-N,N′,N″-tris(3-pyridyl)-1,3,5-benzene tricarboxamide is easily obtained via the N-methyl amide effect

  摘要：

  The N-methyl amide cis generating effect has been utilised to create a new prearranged tripodant ligand in two synthetic steps from benzene-1,3,5-tricarbuxylic acid. Crystals of rhc ligand itself and of complexes with metal sails such as silver(I) triflate, copper(I) and copper(II) chloride and ruthenium(II) chloride have been prepared and the crystal structures solved by analysis of X-ray diffraction data. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00800-0
• 作为产物：
  描述：

  3-氨基吡啶 在 吡啶 作用下， 生成 N-methyl-N-3-pyridyl-p-toluenesulfonamide
  参考文献：
  名称：

  A new prearranged tripodant ligand N,N′,N″-trimethyl-N,N′,N″-tris(3-pyridyl)-1,3,5-benzene tricarboxamide is easily obtained via the N-methyl amide effect

  摘要：

  The N-methyl amide cis generating effect has been utilised to create a new prearranged tripodant ligand in two synthetic steps from benzene-1,3,5-tricarbuxylic acid. Crystals of rhc ligand itself and of complexes with metal sails such as silver(I) triflate, copper(I) and copper(II) chloride and ruthenium(II) chloride have been prepared and the crystal structures solved by analysis of X-ray diffraction data. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00800-0

文献信息

• Acceleration of Pd-Catalyzed Amide N-Arylations Using Cocatalytic Metal Triflates: Substrate Scope and Mechanistic Study
  作者：Joseph Becica、Graham E. Dobereiner

  DOI：10.1021/acscatal.7b01317

  日期：2017.9.1

  comparison with iodobenzene (PhI). The observation of an aryl halide dependence on rate and various qualitative kinetic experiments are consistent with a mechanism in which ligand exchange of halide for amide (“transmetalation”) is turnover limiting. The mechanism may be different depending on whether PhBr or PhI is used as a coupling partner. Oxidative addition complexes (xantphos)Pd(Ph)(X) (X = Br, I;

  助催化三氟甲磺酸金属盐助剂加速了酰胺与芳基卤化物的钯/黄磷催化的交叉偶联。一项对氮亲核试剂的调查显示，当Al（OTf）3时，各种N-芳基酰胺产品的收率都有所提高除了某些例外，它被用作催化添加剂。初始催化速率表明，与溴代碘苯（PhI）相比，使用溴代苯（PhBr）时路易斯酸的加速作用更为明显。芳基卤化物对速率的依赖性以及各种定性动力学实验的观察结果与卤化物配体交换为酰胺（“过渡金属化”）受到限制的机理是一致的。该机制可能会有所不同，具体取决于将PhBr或PhI用作偶联伴侣。制备了氧化加成络合物（xantphos）Pd（Ph）（X）（X = Br，I; xantphos = 4,5-双（二苯基膦基）-9,9-二甲基x吨），可能是催化的中间体; 与Yb（OTf）3的不同相互作用 在溶液中类似于催化机理的卤化物依赖性，我们提出该机理源自催化过程中可逆的路易斯酸介导的卤化物抽象。
• Cross coupling of 3-bromopyridine and sulfonamides (R1NHSO2R2·R1=H, Me, alkyl; R2=alkyl and aryl) catalyzed by CuI/1,3-di(pyridin-2-yl)propane-1,3-dione
  作者：Xiaojun Han

  DOI：10.1016/j.tetlet.2009.11.037

  日期：2010.1

  N-(3-Pyridinyl)-substituted secondary and tertiary sulfonamides have been synthesized in good to excellent yields by the reaction of 3-bromopyridine with primary and secondary alkyl and aryl sulfonamides (MeSO2NH2, MeSO2NHMe, TolSO(2)NH(2), TolSO(2)NHMe, 1,3-propanesultam, and 1,4-butanesultam), catalyzed by CuI (20 mol %) and 1,3-di(pyridin-2-yl)propane-1,3-dione (20 mol %) with K2CO3 (200 mol %) in DMF (0.17 M for ArBr) at 110-120 degrees C over 36-40 h. 2-Bromopyridine, 4-bromopyridine, and a wide variety of substituted phenyl bromides can also be successfully coupled with sulfonamides under these reaction conditions. (C) 2009 Elsevier Ltd. All rights reserved.
• Kalatzis, Evangelos; Papadopoulos, Panayiotis, Journal of the Chemical Society. Perkin transactions II, 1981, p. 248 - 255
  作者：Kalatzis, Evangelos、Papadopoulos, Panayiotis

  DOI：——

  日期：——
• A new prearranged tripodant ligand N,N′,N″-trimethyl-N,N′,N″-tris(3-pyridyl)-1,3,5-benzene tricarboxamide is easily obtained via the N-methyl amide effect
  作者：Mikkel Jørgensen、Frederik C Krebs

  DOI：10.1016/s0040-4039(01)00800-0

  日期：2001.7

  The N-methyl amide cis generating effect has been utilised to create a new prearranged tripodant ligand in two synthetic steps from benzene-1,3,5-tricarbuxylic acid. Crystals of rhc ligand itself and of complexes with metal sails such as silver(I) triflate, copper(I) and copper(II) chloride and ruthenium(II) chloride have been prepared and the crystal structures solved by analysis of X-ray diffraction data. (C) 2001 Elsevier Science Ltd. All rights reserved.