5-methyl-[1,1'-biphenyl]-2-sulfonamide | 936841-54-2

• 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: 5-methyl-[1,1'-biphenyl]-2-sulfonamide
• 英文别名: 4-Methyl-2-phenylbenzene-1-sulfonamide；4-methyl-2-phenylbenzenesulfonamide
• CAS: 936841-54-2
• 化学式: C₁₃H₁₃NO₂S
• 分子量: 247.318
• InChiKey: TWELKPYCOOKHED-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  68.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-methyl-[1,1'-biphenyl]-2-sulfonamide 、 6-[(2-methoxyethyl)(methyl)amino]-1-benzofuran-2-carboxylic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以30 mg的产率得到6-[(2-methoxyethyl)(methyl)amino]-N-(5-methyl[1,1'-biphenyl]-2-sulfonyl)-1-benzofuran-2-carboxamide
  参考文献：
  名称：

  [EN] ACYL SULFONAMIDES FOR TREATING CANCER
  [FR] ACYLSULFONAMIDES POUR LE TRAITEMENT DU CANCER

  摘要：

  本发明提供了一般式(I)的酰基磺酰胺化合物：其中X、R1、R2、R3、R4、R5、R6、Ra和Rb如本文所述和定义的那样，制备所述化合物的方法，用于制备所述化合物的有用中间体化合物，包含所述化合物的药物组合物和组合物，以及利用所述化合物制造用于治疗或预防疾病的药物组合物，特别是治疗或预防过度增殖性疾病的药物组合物，作为唯一药剂或与其他活性成分结合使用，以及治疗和/或预防疾病的方法，特别是癌症，更特别是KAT6A和/或KAT6B在局部扩增的癌症，所述方法包括向需要的受试者施用至少一种式(I)化合物的有效量。

  公开号：

  WO2020216701A1
• 作为产物：
  描述：

  2-iodo-4-methyl-N-(2-phenylpropan-2-yl)benzenesulfonamide 在 四(三苯基膦)钯 caesium carbonate 、 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 24.17h， 生成 5-methyl-[1,1'-biphenyl]-2-sulfonamide
  参考文献：
  名称：

  Directed Ortho Metalation−Cross Coupling Strategies. N-Cumyl Arylsulfonamides. Facile Deprotection and Expedient Route to 7- and 4,7-Substituted Saccharins

  摘要：

  By using the powerful N-cumylsulfonamide directed metalation group (DMG), a series of 2-substituted derivatives were prepared according to the directed ortho metalation (DoM) tactic (Table 1). Mild conditions for N-decumylation and other simple transformations of the products have been achieved (Scheme 2). The 3-silyloxy sultam 12 undergoes further DoM to give formyl, thiomethyl, iodo, and amide derivatives 13a-g of potential value for saccharin synthesis (Table 2). An effective route to target 7-aryl saccharins via Suzuki cross coupling (Table 3) followed by further metalation-carbamoylation and cyclization (Table 5) is described. 4,7-Disubstituted saccharins have been obtained by similar sequences (Scheme 3). Mild TFA-mediated N-decumylation furnishes substituted primary arylsulfonamides (Table 4).

  DOI：

  10.1021/jo062385v

文献信息

• Palladium(II)/copper(I)-catalyzed sequential CH arylation and oxidative CN bond cleavage of aryl sulfonamino acids: Efficient one-pot synthesis of primary biaryl sulfonamides
  作者：Wei Liu、Yongli Zhao、Fei Yi、Junmin Chen

  DOI：10.1016/j.tet.2016.10.056

  日期：2016.12

  A versatile strategy for the one-pot synthesis of primary biaryl-based sulfonamides has been developed via a tandem process consisting of palladium-catalyzed CH arylation and subsequent copper-catalyzed oxidative CN bond cleavage of aryl sulfonamino acids. Both electron-withdrawing and electron-donating functionalities can be introduced into the ortho positions of arenes bearing a variety of substituents

  通过串联方法开发了一种通用的基于联芳基伯酰胺的单罐合成策略，该方法包括钯催化的C H芳基化和随后的铜催化的芳基磺胺酸的氧化C N键裂解。吸电子和给电子功能都可以引入带有多种取代基的芳烃的邻位。氨基酸部分不仅充当引导基团，而且充当氨合成等同物。重要的是，通过使用空气作为唯一的氧化剂，在催化CuI的存在下，该导向基团被顺利地除去。
• Palladium-Catalyzed Site-Selective C−H Functionalization of Weakly Coordinating Sulfonamides: Synthesis of Biaryl Sulfonamides
  作者：Rajeshwer Vanjari、Tirumaleswararao Guntreddi、Krishna Nand Singh

  DOI：10.1002/asia.201501385

  日期：2016.3.4

  A novel and site selective C−H functionalization of unsubstituted sulfonamides has been developed for the synthesis of ortho aryl sulfonamides. The reaction involves highly regioselective ortho mono arylation of weakly coordinating SO2NH2 directing group by means of aryl iodides. Palladium acetate in the presence of silver(I) oxide is found to be the most effective catalytic system.

  未取代的磺酰胺的一个新颖和选择性的位点C-H官能化已开发用于合成邻芳基磺酰胺。该反应涉及借助于芳基碘化物的弱配位的SO 2 NH 2导向基团的高度区域选择性邻位单芳基化。发现在氧化银（I）存在下的乙酸钯是最有效的催化体系。
• Sulfonimide catalysts for coatings
  申请人：CYTEC TECHNOLOGY CORP.

  公开号：EP0509138B1

  公开（公告）日：1995-08-02
• ACYL SULFONAMIDES FOR TREATING CANCER
  申请人：Bayer Aktiengesellschaft

  公开号：US20220226279A1

  公开（公告）日：2022-07-21

  The present invention provides acyl sulfonamide compounds of general formula (I): in which X, R 1 , R 2 , R 3 , R 4 , R 5 , R 6′ R a and R b are as described and defined herein, methods of preparing said compounds, intermediate compounds useful for preparing said compounds, pharmaceutical compositions and combinations comprising said compounds, and the use of said compounds for manufacturing pharmaceutical compositions for the treatment or prophylaxis of diseases, in particular of hyperproliferative disorders, as a sole agent or in combination with other active ingredients as well as methods of treating and/or prophylaxing diseases, particularly cancer, more particularly cancer in which KAT6A and/or KAT6B is focally amplified, said method comprising administering an effective amount of at least one compound of formula (I) to a subject in need thereof.
• US5256493A
  申请人：——

  公开号：US5256493A

  公开（公告）日：1993-10-26