N-phenyl-N'-tosylacetimidamide | 27049-62-3

• 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-phenyl-N'-tosylacetimidamide
• 英文别名: N-phenyl-N'-(toluene-4-sulfonyl)-acetamidine；N-Phenyl-N'-(toluol-4-sulfonyl)-acetamidin；N'-(4-Methylbenzene-1-sulfonyl)-N-phenylethanimidamide；N'-(4-methylphenyl)sulfonyl-N-phenylethanimidamide
• CAS: 27049-62-3
• 化学式: C₁₅H₁₆N₂O₂S
• 分子量: 288.37
• InChiKey: FFRDBRKNVDQCDO-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  437.1±38.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  对甲苯磺酰叠氮 、 硫代乙酰苯胺 以 乙醇 为溶剂， 反应 20.0h， 以46%的产率得到N-phenyl-N'-tosylacetimidamide
  参考文献：
  名称：

  偶极矩和亲电性对硫酰胺与磺酰叠氮化物点击型偶联反应性质的评价

  摘要：

  描述了由硫代酰胺和磺酰基叠氮化物形成磺酰基am的实验和计算研究的合作。数据支持偶合反应的非证实性两步途径，并且还表明硫酰胺的偶极矩和磺酰叠氮化物的亲电性将是影响反应效率的重要因素。通过对这些因素的初步计算机评估，证明了偶联反应的简单反应性预测，由此我们成功地从库存中的几种硫代酰胺和磺酰叠氮化物中成功选出了一对具有高反应性的良好反应物。

  DOI：

  10.1016/j.tetlet.2016.02.028

文献信息

• Iodobenzene Catalyzed C–H Amination of <i>N</i>-Substituted Amidines Using <i>m</i>-Chloroperbenzoic Acid
  作者：Santhosh Kumar Alla、Rapolu Kiran Kumar、Pradeep Sadhu、Tharmalingam Punniyamurthy

  DOI：10.1021/ol400274f

  日期：2013.3.15

  The oxidative C–H amination of N″-aryl-N′-tosyl/N′-methylsulfonylamidines and N,N′-bis(aryl)amidines has been accomplished using iodobenzene as a catalyst to furnish 1,2-disubstituted benzimidazoles in the presence of mCPBA as a terminal oxidant at room temperature. The reaction is general, and the target products can be obtained in moderate to high yields.

  的氧化C-H的胺化Ñ “ -芳基- ñ '-tosyl / Ñ '-methylsulfonylamidines和N，N-双（芳基）脒已经使用碘苯作为催化剂在配料1,2-二取代的苯并咪唑完成在室温下存在m CPBA作为末端氧化剂。该反应是一般性的，可以以中等至高收率获得目标产物。
• Three component reaction of aryl diazonium salt with sulfonamide &amp; actonitrile to synthesize N-sulfonyl amidine
  作者：Yuan Zhang、Zili Chen

  DOI：10.1016/j.tetlet.2018.10.027

  日期：2018.11

  N-sulfonyl amidine compounds through three-component reaction of aryl diazonium salts with sulfonamides and acetonitrile, in which, nitrilium ion intermediate, generated from the reaction of aryldiazonium salt with nitrile, was subsequently trapped by sulfonamides. A series of N-sulfonyl amidine derivatives were synthesized by using various types of aryl diazonium salts, sulfonamides and nitriles. In addition

  开发了一种通过芳基重氮盐与磺酰胺和乙腈的三组分反应制备N-磺酰基am化合物的新方法，其中芳基重氮盐与腈反应生成的腈离子中间体随后被磺酰胺捕获。通过使用各种类型的芳基重氮盐，磺酰胺和腈合成了一系列N-磺酰基am衍生物。另外，吲哚基亚胺产物也可以通过使用吲哚作为亲核试剂来捕获腈离子中间体来制备。
• Regitz,M.; Himbert,G., Justus Liebigs Annalen der Chemie, 1970, vol. 734, p. 70 - 85
  作者：Regitz,M.、Himbert,G.

  DOI：——

  日期：——
• 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.
• Logemann; Artini, Chemische Berichte, 1958, vol. 91, p. 2574,2577
  作者：Logemann、Artini

  DOI：——

  日期：——