(E)-N,N-dimethyl-N'-tosylformimidamide

• 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: (E)-N,N-dimethyl-N'-tosylformimidamide
• 英文别名: N,N-dimethyl-N'-tosylformamidine；N-[(e)-(dimethylamino)methylidene]-4-methylbenzenesulfonamide；N,N-dimethyl-N'-(4-methylphenyl)sulfonylmethanimidamide
• 化学式: C₁₀H₁₄N₂O₂S
• 分子量: 226.299
• InChiKey: AWICAOQZHLERQF-DHZHZOJOSA-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

• 作为反应物：
  描述：

  (E)-N,N-dimethyl-N'-tosylformimidamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以94%的产率得到对甲苯磺酰胺
  参考文献：
  名称：

  由草酰氯介导的 Vilsmeier 试剂的原位形成：一种用于选择性合成 N-磺酰甲脒的工具

  摘要：

  N-磺酰基甲脒由磺酰胺或N-酰化磺酰胺使用从N,N-二取代甲酰胺和草酰氯原位获得的Vilsmeier试剂制备。光学活性底物在该过程中没有外消旋。N-磺酰基甲脒的有效和温和裂解可以通过水合肼在乙醇中实现。整个过程构成了一种简单的方法来保护和去保护磺酰胺部分。

  DOI：

  10.1002/ejoc.201300402
• 作为产物：
  描述：

  三甲基-(4-甲基苯基)锡烷 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 (E)-N,N-dimethyl-N'-tosylformimidamide
  参考文献：
  名称：

  Tin for organic synthesis. 10. Unconventional regiospecific syntheses of aromatic carbonamides and thiocarbonamides by means of tin-mediated Friedel-Crafts reactions

  摘要：

  Friedel-Crafts reactions of stannylarenes 1 with tosyl isocyanate (TsNCO, 2) give N-tosylcarbonamides 3 via ipso substitution of the stannyl group. Thus, unconventionally substituted aromatic carbonamides can be obtained. The combination of the reaction of 1 and 2 with that of 1 and chlorosulfonyl isocyanate (14) allows one-pot syntheses of N-(arylsulfonyl)-substituted aromatic carbonamides with optional substitution patterns on both aromatic rings. The known ipso-specific substitutions of stannylarenes with 14 are extended to bi- and tricyclic arenes as well as to thiophenes 6 and 22. One stannyl group can serve as a leaving group for two aromatic systems, as shown with diaryldialkyltins 29. Also, stannylalkanes such as 27 react with 14 to afford alkylsulfonyl isocyanates and products of further reactions, such as 28. From the reactions of 1 with ethoxycarbonyl isothiocyanate (32), ortho- and meta-substituted aromatic thiocarbonamides 33 which are potential precursors for further syntheses, are accessible. The scope, limitations, and mechanism of these electrophilic substitutions are outlined.

  DOI：

  10.1021/jo00077a020

文献信息

• Three-component synthesis of N-sulfonylformamidines in the presence of magnetic cellulose supported N-heterocyclic carbene-copper complex, as an efficient heterogeneous nanocatalyst
  作者：Salman Shojaei、Zarrin Ghasemi、Aziz Shahrisa

  DOI：10.1016/j.tetlet.2017.08.075

  日期：2017.10

  A cellulose based magnetic nanocomposite possessing NHC-Cu Complex has been synthesized and characterized. It was then applied as a highly active catalyst in one-pot three-component reaction of sulfonyl azides, secondary amines and triethylamine to afford N-sulfonylformamidines. Copper catalyzed oxidative transformation of C-N bond of triethylamine is a key step to give desired products. In contrast

  已经合成并表征了具有NHC-Cu配合物的纤维素基磁性纳米复合材料。然后将其用作高活性催化剂，用于磺酰叠氮化物，仲胺和三乙胺的一锅三组分反应，得到N-磺酰基甲am。铜催化三乙胺的CN键的氧化转化是获得所需产物的关键步骤。与常规仲胺的良好反应性相反，芳族胺和含NH的杂芳族化合物在这些反应中没有活性。而且，所使用的可以被外磁体回收的纳米催化剂多次显示出合理的催化活性。
• Electrochemically generated <i>N</i>-iodoaminium species as key intermediates for selective methyl sulphonylimination of tertiary amines
  作者：Binbin Huang、Chao Yang、Jia Zhou、Wujiong Xia

  DOI：10.1039/c9cc09869k

  日期：——

  This study presents a straightforward protocol for approaching N-sulphonylamidines via an electricity-driven, iodine-mediated cross dehydrogenative condensation (CDC) between sulphonamides and tertiary amines.

  这项研究展示了一个直接的协议，用于通过电驱动、碘介导的磺酰胺和三级胺之间的交叉脱氢缩合反应（CDC）来合成N-磺酰亚胺。
• Bromoform reaction of tertiary amines with N,N-dibromosulfonamides or NBS/sulfonamides
  作者：Jie Chen、Yu-Ping Guo、Ming-Hui Sun、Guo-Tao Fan、Ling Zhou

  DOI：10.1039/c4cc05578k

  日期：——

  A new bromoform reaction of tertiary amines with N,N-dibromosulfonamides or NBS/sulfonamides has been developed. A series of amidines were prepared with moderate to good yields via a Csp(3)-Csp(3) bond cleavage.

  已经开发出叔胺与N，N-二溴磺酰胺或NBS /磺酰胺的新的溴仿反应。通过Csp（3）-Csp（3）键裂解制备了一系列中等至良好收率的am。
• Visible-Light-Mediated Sulfonylimination of Tertiary Amines with Sulfonylazides Involving C_sp³–C_sp³ Bond Cleavage
  作者：Jiao Gui、Haisheng Xie、Huanfeng Jiang、Wei Zeng

  DOI：10.1021/acs.orglett.9b00786

  日期：2019.4.19

  Visible-light-induced cross-coupling of arylsulfonyl azides with tertiaryamines in the presence of Eosin Y at room temperature has been achieved. This transformation features alkyl C–C bond cleavage and provides a green approach to N-sulfonylamidines under mild conditions.

  在室温下，在曙红Y存在下，已经实现了可见光诱导的芳基磺酰叠氮化物与叔胺的交叉偶联。这种转化具有烷基C–C键断裂的特性，并在温和条件下为N-磺酰lam提供了绿色的方法。
• Catalyst-free one-pot, four-component approach for the synthesis of di- and tri-substituted<i>N</i>-sulfonyl formamidines
  作者：Ai-Ran Liu、Lei Zhang、Jiao Li、Abudureheman Wusiman

  DOI：10.1039/d1ra00772f

  日期：——

  A straightforward one-pot, multicomponent approach was developed to synthesize di- and tri-substituted N-sulfonyl formamidines from sulfonyl chlorides, NaN3, ethyl propiolate, and primary/secondary amines under mild conditions without catalysts or additives. Structural analysis of the di-substituted sulfonyl formamidines indicated formation of the E-syn/anti isomeric form. Tri-substituted analogues

  开发了一种简单的一锅多组分方法，在温和条件下，无需催化剂或添加剂，由磺酰氯、NaN3、丙炔酸乙酯和伯/仲胺合成二取代和三取代的 N-磺酰基甲脒。双取代磺酰甲脒的结构分析表明形成了E-顺式/反式异构体形式。三取代的类似物仅形成E-异构体。