(E)-1,1,1-trifluoro-N-(2-styrylphenyl)methanesulfonamide | 53984-17-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1,1,1-trifluoro-N-(2-styrylphenyl)methanesulfonamide
• 英文别名: 1,1,1-trifluoro-N-[2-[(E)-2-phenylethenyl]phenyl]methanesulfonamide
• CAS: 53984-17-1
• 化学式: C₁₅H₁₂F₃NO₂S
• 分子量: 327.327
• InChiKey: UHNDXYGAMQDDEI-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  (E)-1,1,1-trifluoro-N-(2-styrylphenyl)methanesulfonamide 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 三氯乙烷 为溶剂， 反应 2.0h， 以66%的产率得到N-Tf-2-phenylindole
  参考文献：
  名称：

  Metal-Free C–H Amination for Indole Synthesis

  摘要：

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

  DOI：

  10.1021/ol5015398
• 作为产物：
  描述：

  2-溴苯胺 在 吡啶 、 palladium diacetate 、 三乙胺 、 三(邻甲基苯基)磷 作用下， 反应 2.0h， 生成 (E)-1,1,1-trifluoro-N-(2-styrylphenyl)methanesulfonamide
  参考文献：
  名称：

  Metal-Free C–H Amination for Indole Synthesis

  摘要：

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.

  DOI：

  10.1021/ol5015398

文献信息

• Palladium-catalyzed denitrogenative functionalizations of benzotriazoles with alkenes and 1,3-dienes
  作者：Yuanhao Wang、Yuanhe Li、Yijun Fan、Zhiguo Wang、Yefeng Tang

  DOI：10.1039/c7cc07543j

  日期：——

  Pd-Catalyzed denitrogenative functionalizations of benzotriazoles with alkenes and 1,3-dienes have been developed, which enable the rapid access of diverse ortho-amino styrenes and 2-vinylindolines, respectively. This study shows the great potential of benzotriazoles as a [1C]-synthon in cross-coupling reactions and an aza-[3C]-synthon in cycloaddition reactions.

  已经开发了Pd催化的具有烯烃和1，3-二烯的苯并三唑的脱氮官能化，这使得能够分别快速地获得各种邻氨基苯乙烯和2-乙烯基吲哚啉。这项研究表明，苯并三唑在交叉偶联反应中作为[1C]合成子和在环加成反应中作为aza- [3C]合成子的巨大潜力。
• Antiinflammatory fluoroalkanesulfonanilides. 3. Other fluoroalkanesulfonamido diaryl systems
  作者：G. G. I. Moore、J. K. Harrington、K. F. Swingle

  DOI：10.1021/jm00238a013

  日期：1975.4

  A series of isosteres of 3-benzoyltrifluoromethanesulfonanilide involving alternatives to the carbonyl linking group was synthesized and screened for antiinflammatory activity in the carrageenan rat paw edema test. The systems examined were of the type m-CF3SO2NH-C6H4-X-C6H5, where X was -CROH-, -CHR-, -CH(OH)CH2-, -COCH2-, -CH2CO-, greater than C equal to CR2, -CR equal to CH, -C identical to C-, -CH2CH2-, CONH-, -NR-, -O-, -S(O)n- (n equal to 0,1,2), and carbon-carbon single bond. Many ortho and para derivatives were also tested. Several of these new trifluoromethanesulfonanilides proved equipotent with phenylbutazone. The effects on the anticarrageenan activity of both the nature and ring position of X are discussed.
• Metal-Free C–H Amination for Indole Synthesis
  作者：Young Ho Jang、So Won Youn

  DOI：10.1021/ol5015398

  日期：2014.7.18

  An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.