N-benzyl-3'-trifluoromethylphenylsulfonamide

• 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-benzyl-3'-trifluoromethylphenylsulfonamide
• 英文别名: N-benzyl-3-(trifluoromethyl)benzene-1-sulfonamide；N-benzyl-3-(trifluoromethyl)benzenesulfonamide
• 化学式: C₁₄H₁₂F₃NO₂S
• mdl: MFCD01269304
• 分子量: 315.316
• InChiKey: AYLPMXBJOWBNTH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyl-3'-trifluoromethylphenylsulfonamide 在 吡啶 、 copper(l) iodide 、 四甲基乙二胺 、 氧气 、 sodium carbonate 、 copper dichloride 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 28.33h， 生成 N,N'-(buta-1,3-diyne-1,4-diyl)bis(N-benzyl-3-(trifluoromethyl)benzenesulfonamide)
  参考文献：
  名称：

  Synergetic copper/zinc catalysis: synthesis of aryl/heteroaryl-fused 1H-pyrrolo[3,2-c]pyridines

  摘要：

  本协议重点介绍了一种新颖的单步合成芳基/杂环芳基融合的1H-吡咯[3,2-c]吡啶，使用催化量的Cu(II)和Zn(II)盐。

  DOI：

  10.1039/d1cc05514c
• 作为产物：
  描述：

  3-三氟甲基苯磺酰氯 、 苄胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-benzyl-3'-trifluoromethylphenylsulfonamide
  参考文献：
  名称：

  Ruthenium trichloride catalyzed synthesis of 2,3-unsaturated-N-glycosides via Ferrier azaglycosylation

  摘要：

  An efficient, economical and mild protocol for the synthesis of 2,3-unsaturated-N-glycosides has been developed using ruthenium(III) chloride. The Ferrier azaglycosylation of glycals with various N-nucleophiles such as sulfonamides, benzamides, carbamates and N-substituted sulfonamides proceeded smoothly to afford the corresponding 2,3-unsaturated-N-glycosides or 'N-pseudoglycals' in good yields (64-98%). High alpha-anomeric selectivity was observed with N-substituted sulfonamides such as N-benzyl or N-phenyl sulfonamides under similar conditions. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.10.024

文献信息

• Photo-induced synthesis of β-sulfonyl imides from carboxylic acids
  作者：Linwei Zeng、Jian Jin、Jixiao He、Sunliang Cui

  DOI：10.1039/d1cc02559g

  日期：——

  A photo-induced imidation process of carboxylic acids is described. Numerous carboxylic acids could convert to β-sulfonyl imides in the presence of N-sulfonyl ynamides under visible light irradiation. Control experiments and mechanistic studies demonstrate that this imidation process involves a hydroacyloxylation/radical rearrangement cascade. This protocol represents a direct imidation method from

  描述了羧酸的光诱导酰亚胺化过程。在可见光照射下，在N-磺酰基炔酰胺的存在下，许多羧酸可以转化为 β-磺酰亚胺。对照实验和机理研究表明，这种酰亚胺化过程涉及氢酰氧基化/自由基重排级联。该协议代表了一种在温和条件下从羧酸直接酰亚胺化的方法，具有广泛的范围和高原子经济性。
• Keteniminium‐Driven Umpolung Difunctionalization of Ynamides
  作者：Shubham Dutta、Shengwen Yang、Rajeshwer Vanjari、Rajendra K. Mallick、Vincent Gandon、Akhila K. Sahoo

  DOI：10.1002/anie.201915522

  日期：2020.6.26

  synthesis of novel triaryl‐substituted enamides is described. This transformation represents the first example of an umpolung regioselective unsymmetrical syn ‐1,2‐diarylation/aryl‐olefination of ynamides. The aryl moieties of the diazonium salt (electrophile) and boronic acid (nucleophile) are explicitly incorporated in the electrophilic α‐ and nucleophilic β‐position, respectively, of the ynamide

  描述了三酰胺的三组分钯催化偶联，用于合成新型的三芳基取代的酰胺类化合物。这种转变代表了区域选择性非对称合成蛋白的第一个例子酰胺的1,2-二芳基化/芳基烯化。重氮盐（亲电子）和硼酸（亲核）的芳基部分分别明确地结合到乙酰胺的亲电子α-和亲核β-位，形成了一个含氮四取代烯烃的单一异构体。范围很广（68个示例），显示出极好的功能组容限。DFT计算证实了机械循环和区域选择性的基本原理。还研究了烯酰胺产物的化学选择性和合成潜力。
• Three Component <i>syn</i> ‐1,2‐Arylmethylation of Internal Alkynes**
  作者：Shubham Dutta、Akhila K. Sahoo

  DOI：10.1002/anie.202300610

  日期：2023.3.13

  A regio- and stereoselective Pd-catalyzed three-component syn-1,2-arylmethylation of internal alkynes is reported. A library of methyl containing tetra-substituted olefins was successfully built using readily available and bench-stable coupling partners, iodo-arenes, and methyl boronic acid.

  报告了内部炔烃的区域选择性和立体选择性 Pd 催化的三组分顺式-1,2-芳基甲基化。使用现成且稳定的偶联伙伴、碘代芳烃和甲基硼酸，成功构建了一个包含四取代烯烃的甲基库。
• Copper/Zinc-Catalyzed Stitching of 2-Carbonylanilines with Bis(ynamides): Access to Pyrrolo[2,3-b]quinolines and Its Photophysical Studies
  作者：Shivani Choudhary、Gayyur、Arnab Mandal、Abhijit Patra、Ruchir Kant、Nayan Ghosh

  DOI：10.1021/acs.joc.4c00267

  日期：2024.5.3

  Herein, a one-pot desulfonylative protocol enabled by copper(II)/zinc(II) salts to access pyrrolo[2,3-b]quinolines in good to excellent yields from 2-carbonylanilines and ynamide-derived buta-1,3-diynes has been reported. Significantly, various 2-carbonylanilines carrying reactive functional groups are well tolerated. Moreover, a gram-scale synthesis and synthetic application highlight the practical

  本文中，通过铜(II)/锌(II)盐实现的一锅脱磺酰化方案能够以良好至优异的产率从2-羰基苯胺和炔酰胺衍生的buta-1,3-获得吡咯并[2,3- b ]喹啉。已有报道称二炔。值得注意的是，各种带有反应性官能团的 2-羰基苯胺具有良好的耐受性。此外，克级合成和合成应用突出了当前协议的实用性。值得注意的是，吡咯并[2,3- b ]喹啉的荧光特性已被记录，并且它们作为活细胞成像中的荧光探针的潜在用途已被证明。
• Zn(II) Triflate-Catalyzed<i>N</i>-Glycosylation: Synthesis of Sulfonamide and Amide Functionalized 2,3-Unsaturated Glycosides
  作者：Thurpu Raghavender Reddy、Suresh Kumar Battina、Sudhir Kashyap

  DOI：10.1080/07328303.2015.1018994

  日期：2015.3.24

  GRAPHICAL ABSTRACT[GRAPHICS]A highly efficient and mild method for the synthesis of glycosyl sulfonamides and glycosyl amides from glycal has been described using Zn(OTf)(2) as an economical and environmentally friendly catalyst. Various N-nucleophiles comprising sulfonamides, benzamides, and carbamates were glycosylated with glycals to obtain corresponding 2,3-unsaturated N-glycosides in good yields.