4-methyl-N-(3-methylenepent-4-enyl)benzenesulfonamide | 165903-17-3

• 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: 4-methyl-N-(3-methylenepent-4-enyl)benzenesulfonamide
• 英文别名: 3-methylene-5-(N-tosylamino)-1-pentene；4-methyl-N-(3-methylene-4-pentenyl)benzenesulfonamide；4-methyl-N-(3-methylidenepent-4-enyl)benzenesulfonamide
• CAS: 165903-17-3
• 化学式: C₁₃H₁₇NO₂S
• 分子量: 251.349
• InChiKey: FYWPAXSNMSAYEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-methyl-N-(3-methylenepent-4-enyl)benzenesulfonamide 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以120 mg的产率得到4-甲基-1-[(4-甲基苯基)磺酰基]-1,2,3,6-四氢吡啶
  参考文献：
  名称：

  Enyne Metathesis/Brønsted Acid-Promoted Heterocyclization

  摘要：

  The "one-pot" synthesis of nitrogen heterocycles and an oxygen heterocycle by enyne metathesis and in situ cyclization is reported.

  DOI：

  10.1021/jo802582k
• 作为产物：
  描述：

  N-tosyl-2-methyl-2-vinylazetidine 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以77%的产率得到4-methyl-N-(3-methylenepent-4-enyl)benzenesulfonamide
  参考文献：
  名称：

  Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion

  摘要：

  Ring opening reactions of 1-acetyl-4-vinyl-2-azetidinones in the presence of palladium(0)-n-Bu(3)P catalyst gave 2,4-pentadienamides in good yields, whereas 2-substituted-1,3-dienes were produced by the reaction of 1-sulfonyl-2-vinyl-2-methylazetidines. Ring opening dimerization took place to give 1,7-ditrifluoromethanesulfonyl-1,7-diazacyclododecane in the reaction of 1-trifluoromethanesulfonyl-2-vinylazetidine.

  DOI：

  10.1016/0040-4020(95)00217-v

文献信息

• Decarboxylative Ring Contractions and Olefin Insertions of Vinyl Oxazinanones
  作者：Chao Wang、Jon A. Tunge

  DOI：10.1021/ol0610744

  日期：2006.7.1

  6-Vinyl oxazinanones undergo catalytic, diastereoselective, decarboxylative ring contraction to form vinyl azetidines in good yield. Performing the decarboxylation in the presence of Michael acceptors results in decarboxylative olefin insertion to provide diastereoenriched substituted vinyl piperidines.
• Palladium-catalyzed ring-opening reactions of 1-acetyl-4-vinyl-2-azetidinones and 1-sulfonyl-2-vinylazetidines. Role of intramolecular participation of amide anion
  作者：Akiharu Satake、Hideo Ishii、Isao Shimizu、Yoichi Inoue、Hajime Hasegawa、Akio Yamamoto

  DOI：10.1016/0040-4020(95)00217-v

  日期：1995.5

  Ring opening reactions of 1-acetyl-4-vinyl-2-azetidinones in the presence of palladium(0)-n-Bu(3)P catalyst gave 2,4-pentadienamides in good yields, whereas 2-substituted-1,3-dienes were produced by the reaction of 1-sulfonyl-2-vinyl-2-methylazetidines. Ring opening dimerization took place to give 1,7-ditrifluoromethanesulfonyl-1,7-diazacyclododecane in the reaction of 1-trifluoromethanesulfonyl-2-vinylazetidine.
• Enyne Metathesis/Brønsted Acid-Promoted Heterocyclization
  作者：Kyle P. Kalbarczyk、Steven T. Diver

  DOI：10.1021/jo802582k

  日期：2009.3.6

  The "one-pot" synthesis of nitrogen heterocycles and an oxygen heterocycle by enyne metathesis and in situ cyclization is reported.