N,N-dimethyl-N′-(o-tolylsulfonyl)formimidamide | 1344029-80-6

• 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,N-dimethyl-N′-(o-tolylsulfonyl)formimidamide
• 英文别名: N,N-dimethyl-N'-(o-tolylsulfonyl)formamidine；N,N-dimethyl-N'-(o-tolylsulfonyl)formimidamide；N,N-dimethyl-N'-(2-methylphenyl)sulfonylmethanimidamide
• CAS: 1344029-80-6
• 化学式: C₁₀H₁₄N₂O₂S
• 分子量: 226.299
• InChiKey: KNECHCVXROYVRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  58.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  邻,对甲苯磺酰胺 、 N,N-二甲基甲酰胺 在 N-溴代丁二酰亚胺(NBS) 、 水 作用下， 以87%的产率得到N,N-dimethyl-N′-(o-tolylsulfonyl)formimidamide
  参考文献：
  名称：

  Otherwise inert reaction of sulfonamides/carboxamides with formamides via proton transfer-enhanced reactivity

  摘要：

  NBS介导的磺胺/羧酰胺和甲酰胺的加成-消除反应分别提供了N-磺酰亚胺和N-甲酰芳基酰胺，这取决于不同的消除机理。氢键诱导的质子转移导致反应活性增强，并被认为是反应发生的关键驱动力。该方案展示了基于非共价氢键相互作用诱导的质子转移策略构建化学键的可能性。

  DOI：

  10.1039/c3ob27351b

文献信息

• Direct Condensation of Sulfonamide and Formamide: NaI-Catalyzed Synthesis of <i>N</i>-Sulfonyl Formamidine Using TBHP as Oxidant
  作者：Shulin Chen、Yuan Xu、Xiaobing Wan

  DOI：10.1021/ol2024604

  日期：2011.12.2

  A new N-sulfonyl formamidine synthesis was developed via Nal-catalyzed direct condensation of sulfonamide and formamide. The green methodology is featured by high atom economy, easily available starting materials, the lack of need for a transition-metal catalyst, no requirement of hazardous reagent, operational simplicity, and good tolerance with diverse functional groups. Mechanistic studies suggest that the protocol proceeds based upon in situ generated TsN center dot Nal.
• Otherwise inert reaction of sulfonamides/carboxamides with formamides via proton transfer-enhanced reactivity
  作者：Zaihai Niu、Shaoxia Lin、Zhiyong Dong、Hao Sun、Fushun Liang、Jingping Zhang

  DOI：10.1039/c3ob27351b

  日期：——

  NBS-mediated addition–elimination reaction of sulfonamides/carboxamides and formamides afforded N-sulfonylamidines and N-formylarylamides, respectively, depending on the different mechanism of elimination. Hydrogen bond-induced proton transfer leads to enhanced reactivities and was proposed as the key driving force for the reaction to take place. The protocol demonstrates the possibility of constructing chemical bonds based on a proton transfer strategy induced by noncovalent hydrogen bond interaction.

  NBS介导的磺胺/羧酰胺和甲酰胺的加成-消除反应分别提供了N-磺酰亚胺和N-甲酰芳基酰胺，这取决于不同的消除机理。氢键诱导的质子转移导致反应活性增强，并被认为是反应发生的关键驱动力。该方案展示了基于非共价氢键相互作用诱导的质子转移策略构建化学键的可能性。