N-(2-(1H-pyrazol-1-yl)phenyl)-4-methylbenzenesulfonamide | 1379667-34-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-(2-(1H-pyrazol-1-yl)phenyl)-4-methylbenzenesulfonamide
• 英文别名: 4-methyl-N-(2-pyrazol-1-ylphenyl)benzenesulfonamide
• CAS: 1379667-34-1
• 化学式: C₁₆H₁₅N₃O₂S
• 分子量: 313.38
• InChiKey: RJPCXRDVARYWHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  72.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-(1H-pyrazol-1-yl)phenyl)-4-methylbenzenesulfonamide 以 四氢呋喃 、 甲苯 为溶剂， 反应 13.0h， 生成
  参考文献：
  名称：

  Synthesis, characterization and catalytic studies of aluminium complexes containing sulfonamido–oxazolinate or –pyrazolinate ligands

  摘要：

  A series of sulfonamido-oxazolinate ligand precursors, HNSO(2)Ph(H)Oxa, HNSO(2)Ph(Me)Oxa, HNSO(2)Ph(TriMe)Oxa, or sulfonamido-pyrazolinate ligand precursors, HNSO(2)Ph(H)Pz(H), HNSO(2)Ph(Me)Pz(H), HNSO(2)Ph(TriMe)Pz(H), HNSO(2)Ph(F)Pz(H), HNSO(2)Ph(H)Pz(Me), HNSO(2)Ph(Me)Pz(Me), HNSO(2)Ph(TriMe)Pz(Me), have been prepared. Treatment of ligand precursors, HNSO(2)Ph(A)Oxa or HNSO(2)Ph(A)Pz(B), with 1.1 equiv. of AlMe3 in THF affords aluminium sulfonamido-oxazolinate dimethyl complexes, (NSO(2)Ph(A)Oxa)AlMe2 [A = H (1); A = Me (2); A = TriMe, (3)], or aluminium sulfonamido-pyrazolinate dimethyl complexes, (NSO(2)Ph(A)Pz(B))AlMe2 [A = H, B = H (4); A = Me, B = H (5); A = TriMe, B = H (6); A = F, B = H (7); A = H, B = Me (8); A = Me, B = Me (9); A = TriMe, B = Me (10)]. The aluminium bis(sulfonamido-pyrazolinate) methyl complex 5' was isolated from recrystallization of 5 as minor product. The molecular structures of compounds 2, 5' and 8 were determined by single-crystal X-ray diffraction techniques. Their catalytic activities towards the ring opening polymerization of epsilon-caprolactone in the presence of benzyl alcohol are also under investigation. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.12.022
• 作为产物：
  描述：

  对甲苯磺酰氯 在 silver hexafluoroantimonate 、 sodium azide 、 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 sodium acetate 作用下， 以 水 、 1,2-二氯乙烷 、 丙酮 为溶剂， 反应 23.0h， 生成 N-(2-(1H-pyrazol-1-yl)phenyl)-4-methylbenzenesulfonamide
  参考文献：
  名称：

  钌催化直接Ç ？芳烃的H酰胺化，包括弱配位的芳香酮

  摘要：

  Ç  ħ激活：所述的钌催化直接SP 2 ç  ħ酰胺化，通过使用叠氮化物磺酰作为氨基源被呈现（参见方案）的芳烃。各种基材容易酰胺化，包括带有弱配位基团的芳烃。由此获得的产物的合成效用在生物活性杂环的制备中得到证明。

  DOI：

  10.1002/chem.201301025

文献信息

• Expedient C–H Amidations of Heteroaryl Arenes Catalyzed by Versatile Ruthenium(II) Catalysts
  作者：Vedhagiri S. Thirunavukkarasu、Keshav Raghuvanshi、Lutz Ackermann

  DOI：10.1021/ol401321q

  日期：2013.7.5

  Heteroaryl-substituted arenes and heteroarenes were efficiently amidated through ruthenium-catalyzed C–H bond functionalizations with a variety of sulfonyl azides. Particularly, cationic ruthenium(II) complexes proved to be most effective and allowed nitrogenations of electron-rich and electron-deficient arenes with ample substrate scope.

  杂芳基取代的芳烃和杂芳烃通过钌催化的各种磺酰叠氮化物的C–H键官能化反应而得到有效酰胺化。特别是，阳离子钌（II）配合物被证明是最有效的方法，可以使富电子和缺电子的芳烃在足够的底物范围内进行氮化。
• Rhodium-Catalyzed Intermolecular Amidation of Arenes with Sulfonyl Azides via Chelation-Assisted C–H Bond Activation
  作者：Ji Young Kim、Sae Hume Park、Jaeyune Ryu、Seung Hwan Cho、Seok Hwan Kim、Sukbok Chang

  DOI：10.1021/ja303527m

  日期：2012.6.6

  We report the direct amidation of arene C-H bonds using sulfonyl azides as the amino source to release N(2) as the single byproduct. The reaction is catalyzed by a cationic rhodium complex under external oxidant-free conditions in the atmospheric environment. A broad range of chelate group-containing arenes are selectively amidated with excellent functional group tolerance, thus opening a new avenue

  我们报告使用磺酰叠氮化物作为氨基源释放 N(2) 作为单一副产品的芳烃 CH 键的直接酰胺化。该反应在大气环境中的外部无氧化剂条件下由阳离子铑络合物催化。广泛的含螯合基团的芳烃被选择性酰胺化，具有优异的官能团耐受性，从而为实际分子间 CN 键的形成开辟了新途径。
• Manganese-Catalyzed C−H Amidation of Heteroarenes in Water
  作者：Xianqiang Kong、Long Lin、Bo Xu

  DOI：10.1002/adsc.201800544

  日期：2018.8.6

  We have developed an efficient manganese‐catalyzed amidation of various heteroarenes via C−H bond activation using readily available sulfonyl azides. The key step is heteroarene directed electrophilic aromatic metalation using MnBr(CO)5 as catalyst. This method offers excellent chemical yields and regioselectivity with good functional group tolerance. This base metal catalyzed reaction proceeds efficiently

  我们已经开发出了一种高效的锰催化的酰胺化方法，可以使用现成的磺酰叠氮化物通过CH键活化各种杂芳烃。关键步骤是使用MnBr（CO）5作为催化剂的杂芳烃定向亲电芳族金属化。该方法具有出色的化学收率和区域选择性，并具有良好的官能团耐受性。该贱金属催化的反应使用水作为唯一的溶剂并且氮气是唯一的副产物有效地进行。
• Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp²)–H, C(sp³)–H, and Late-Stage Functionalizations
  作者：Xu-Hong Hu、Xiao-Fei Yang、Teck-Peng Loh

  DOI：10.1021/acscatal.6b02015

  日期：2016.9.2

  Air-stable and convenient amidobenziodoxolones as an amidating reagent were disclosed to enable direct amidation on a wide range of C(sp2)–H bonds of (hetero)arenes and alkenes, as well as unactivated C(sp3)–H bonds under RhIII catalysis. The approach to access 49 examples of structurally diverse amides is featured by mild conditions, complete chemoselectivity and regioselectivity, broad substrate scope

  公开了一种空气稳定且方便的酰胺基苯并恶唑烷酮作为酰胺化试剂，可以直接酰胺化广泛的（杂）芳烃和烯烃的C（sp 2）-H键，以及未活化的C（sp 3）-H键Rh III催化。获得49种结构多样的酰胺实例的方法的特点是温和条件，完全的化学选择性和区域选择性，广泛的底物范围（不限于强杂环配位基团）以及对有价值的功能性取代基（如未保护的胺和羟基）的耐受性。该协议的合成适用性也通过生物学上重要的支架的后期功能化得到证明。
• Rhodium(III)-Catalyzed Intermolecular N-Chelator-Directed Aromatic C–H Amidation with Amides
  作者：Huaiqing Zhao、Yaping Shang、Weiping Su

  DOI：10.1021/ol4024776

  日期：2013.10.4

  Rh(III)-catalyzed intermolecular direct aromatic C–H bond amidation with amides has been accomplished under mild reaction conditions. This protocol is applicable to a broad range of N-chelator-containing arenes amidated with aromatic and aliphatic sulfonamides. A possible mechanism is proposed according to the experimental results.

  Rh（III）催化的酰胺间分子间直接芳族C–H酰胺化反应在温和的反应条件下完成。该方案适用于广泛的含芳香族和脂肪族磺酰胺酰胺化的含N螯合剂的芳烃。根据实验结果提出了一种可能的机理。