4-methyl-N-(pyrrolidin-2-ylidene)benzenesulfonamide

• 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-(pyrrolidin-2-ylidene)benzenesulfonamide
• 英文别名: N-(3,4-dihydro-2H-pyrrol-5-yl)-4-methylbenzenesulfonamide
• 化学式: C₁₁H₁₄N₂O₂S
• 分子量: 238.31
• InChiKey: VUOHLZBDUGRFMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-吡咯烷酮 、 对甲苯磺酰胺 在 三乙胺 、 三氯氧磷 作用下， 以 氯苯 为溶剂， 反应 5.0h， 以65%的产率得到4-methyl-N-(pyrrolidin-2-ylidene)benzenesulfonamide
  参考文献：
  名称：

  Facile One-Pot Synthesis of Cyclic N-Sulfonylamidines from Lactam and Sulfonamide

  摘要：

  A simple method has been developed for one-pot synthesis of five-, six- and seven-membered cyclic N-sulfonylamidines from lactams and sulfonamides under mild conditions. The method involves a Vilsmeier like reaction promoted by phosphoryl chloride. Detailed synthetic studies showed that the corresponding substituted N-sulfonylamidines were obtained in moderate to good yields.

  DOI：

  10.3987/com-15-13307

文献信息

• Dirhodium(II) Complexes of 2-(Sulfonylimino)pyrrolidine: Synthesis and Application in Catalytic Benzylic Oxidation
  作者：Abudureheman Wusiman、Xiarepati Tusun、Chong-Dao Lu

  DOI：10.1002/ejoc.201200292

  日期：2012.6

  A new class of dirhodium(II) tetraamidinates derived from 2-(sulfonylimino)pyrrolidines has been prepared through ligand substitution by using dirhodium(II) acetate, in which (3,1) geometric isomers are formed predominantly. Among these complexes, (3,1)-Rh2(Msip)4, exhibits good catalytic performance in benzylic oxidation. In the presence of (3,1)-Rh2(Msip)4 a variety of benzylic derivatives, including

  使用乙酸二铑（II）通过配体取代制备了一类新的衍生自 2-（磺酰基亚氨基）吡咯烷的四脒二铑 (II)，其中主要形成 (3,1) 几何异构体。在这些配合物中，(3,1)-Rh2(Msip)4 在苄基氧化中表现出良好的催化性能。在 (3,1)-Rh2(Msip)4 存在下，多种苄基衍生物，包括强缺电子的芳基烷烃，如 1-乙基-4-硝基苯，在水中很容易被廉价的氧化剂 T-HYDRO 氧化。 R) (70 wt.-% 叔丁基氢过氧化物水溶液)。
• Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis of<i>N</i>-Sulfonylamidine Derivatives
  作者：Jijun Chen、Wenhao Long、Yonggang Yang、Xiaobing Wan

  DOI：10.1021/acs.orglett.8b00867

  日期：2018.5.4

  A novel, secondary amide activation strategy has been developed through the in situ generation of ylides from amides and diazoacetates. Under the developed reaction conditions, Mn-catalyzed ylide formation and interception reaction by sulfonamide delivered a variety of N-sulfonylamidines. Notably, when highly active Zn(OTf)(2) was used as the catalyst, further N-H insertion products were obtained. In contrast with traditional methods, our amide activation strategy is distinguished by accessible starting material, inexpensive catalyst, and broad substrate scope.