N,N-diethyl-N'-(naphthalen-2-ylsulfonyl)formimidamide | 1071654-25-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N-diethyl-N'-(naphthalen-2-ylsulfonyl)formimidamide
• 英文别名: N,N-diethyl-N'-naphthalen-2-ylsulfonylmethanimidamide
• CAS: 1071654-25-5
• 化学式: C₁₅H₁₈N₂O₂S
• 分子量: 290.386
• InChiKey: CWUFGEJKRHPBAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 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：

  2-naphthalenesulphonyl azide 、 三乙胺 在 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以73%的产率得到N,N-diethyl-N'-(naphthalen-2-ylsulfonyl)formimidamide
  参考文献：
  名称：

  An Unexpected Diethyl Azodicarboxylate-Promoted Dehydrogenation of Tertiaryamine and Tandem Reaction with Sulfonyl Azide

  摘要：

  It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides to give the N-sulfonyl amidine derivatives. A number of different substituted tertiaryamines and sulfonyl azides can successfully be coupled, and several functionalized groups are tolerated in this system. The reaction described here is mild, general, and efficient, thus providing an extremely preferable method for synthesis of a variety of N-sulfonyl amidine derivatives.

  DOI：

  10.1021/ja8047514

文献信息

• Air-Induced One-Pot Synthesis of <i>N</i> -Sulfonylformamidines from Sulfonyl Chlorides, NaN₃ , and Tertiary/Secondary Amines
  作者：Wen-Zhu Bi、Wen-Jie Zhang、Zi-Jie Li、Xiao-Yi Xia、Xiao-Lan Chen、Ling-Bo Qu、Yu-Fen Zhao

  DOI：10.1002/ejoc.201901048

  日期：2019.9.22

  Several of N‐sulfonylformamidines were synthesized in one‐pot using easily available sulfonyl chlorides, sodium azide and tertiary/secondary amines in the presence of 5 mol‐% CuBr2 in DCE under aerobic oxidative conditions.

  在有氧氧化条件下，在DCE中存在5 mol％CuBr 2的情况下，使用容易获得的磺酰氯，叠氮化钠和叔/仲胺，在一个锅中合成了几种N-磺酰基甲am 。
• Hexamethyldisilazane-Mediated Amidination of Sulfonamides and Amines with Formamides
  作者：Yu-Chen Chou、Wei-Han Lin、Xiu-Yi Lin、Chin-Ling Kuo、Wan-Qin Zeng、I-Chung Lu、Chien-Fu Liang

  DOI：10.1021/acs.joc.2c01902

  日期：2022.11.18

  Hexamethyldisilazane was reacted with formamides to generate N,N-disubstituent formimidamide, after which a reaction with sulfonamides was induced to form sulfonylformamidines. This protocol can be applied for arylformamidine formation in which anilines are used as substrates under optimized conditions. The advantages of this method are high efficiency, structural diversity in products with good yields

  六甲基二硅氮烷与甲酰胺反应生成N , N-二取代基甲酰亚胺，然后与磺酰胺反应生成磺酰甲脒。该协议可应用于芳基甲脒形成，其中苯胺在优化条件下用作底物。该方法的优点是效率高，产品结构多样，产率高，适用于大规模操作。
• CuCl/CCl₄-Promoted Convenient Synthesis of Sulfonyl Amidines from Tertiary Amines and Sulfonyl Azides
  作者：Xiaoliang Xu、Zhichuang Ge、Dongping Cheng、Lei Ma、Chunshan Lu、Qunfeng Zhang、Nan Yao、Xiaonian Li

  DOI：10.1021/ol1000236

  日期：2010.3.5

  Promoted by CuCl/CCl4, a variety of sulfonyl azides and tertiary amines were successfully coupled to give sulfonyl amidine derivatives in good to excellent yields. A possible mechanism for this reaction is discussed.
• An Unexpected Diethyl Azodicarboxylate-Promoted Dehydrogenation of Tertiaryamine and Tandem Reaction with Sulfonyl Azide
  作者：Xiaoliang Xu、Xiaonian Li、Lei Ma、Ning Ye、Bojie Weng

  DOI：10.1021/ja8047514

  日期：2008.10.29

  It is shown here for the first time that diethyl azodicarboxylate promotes dehydrogenation of tertiaryamines to afford enamines, which subsequently take place in tandem reactions with sulfonyl azides to give the N-sulfonyl amidine derivatives. A number of different substituted tertiaryamines and sulfonyl azides can successfully be coupled, and several functionalized groups are tolerated in this system. The reaction described here is mild, general, and efficient, thus providing an extremely preferable method for synthesis of a variety of N-sulfonyl amidine derivatives.