N-(pyrrolidin-2-ylidene)thiophene-2-sulfonamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 亚胺内酰胺
• 英文名称: N-(pyrrolidin-2-ylidene)thiophene-2-sulfonamide
• 英文别名: N-(3,4-dihydro-2H-pyrrol-5-yl)thiophene-2-sulfonamide
• 化学式: C₈H₁₀N₂O₂S₂
• 分子量: 230.312
• InChiKey: OGRWCXYOMXRFTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  95.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-吡咯烷酮 、 2-噻吩磺酰胺 在 重氮乙酸乙酯 、 manganese(II) perchlorate hexahydrate 作用下， 以 环己烷 为溶剂， 反应 12.0h， 以98%的产率得到N-(pyrrolidin-2-ylidene)thiophene-2-sulfonamide
  参考文献：
  名称：

  Interception of Secondary Amide Ylide with Sulfonamides: Catalyst-Controlled Synthesis ofN-Sulfonylamidine Derivatives

  摘要：

  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.

  DOI：

  10.1021/acs.orglett.8b00867

文献信息

• 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.