N-benzyl-N'-tosylbenzimidamide

• 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-benzyl-N'-tosylbenzimidamide
• 英文别名: N'-benzyl-N-(4-methylphenyl)sulfonylbenzenecarboximidamide
• 化学式: C₂₁H₂₀N₂O₂S
• 分子量: 364.468
• InChiKey: ICMPJSKTPAZFBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  n-苄基苯甲酰胺 、 对甲苯磺酰胺 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58%的产率得到N-benzyl-N'-tosylbenzimidamide
  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

• Tandem Coupling of Azide with Isonitrile and Boronic Acid: Facile Access to Functionalized Amidines
  作者：Zhen Zhang、Baoliang Huang、Guanyu Qiao、Liu Zhu、Fan Xiao、Feng Chen、Bin Fu、Zhenhua Zhang

  DOI：10.1002/anie.201700539

  日期：2017.4.3

  Amidine is a notable nitrogen‐containing structural motif found in bioactive natural products and pharmaceuticals. Herein, a novel rhodium(I)‐catalyzed tandem reaction of readily accessible azides with isonitriles and boronic acids via a carbodiimide intermediate is achieved. This protocol offers an alternative approach toward N‐sulfonyl‐, N‐acyl‐, and N‐ phosphoryl‐functionalized, as well as general

  idine是在生物活性天然产物和药物中发现的显着的含氮结构基序。本文中，通过碳二亚胺中间体实现了易于获得的叠氮化物与异腈和硼酸的新型铑（I）催化串联反应。该协议为N-磺酰基，N-酰基和N-磷酰基官能化以及具有广泛底物范围的常规N-芳基和N-烷基am提供了另一种方法。另外，当使用胺代替时，也可以合成官能化的胍。雌酮衍生的am和格列本脲生物等排体的完成进一步揭示了该策略的实用性。
• 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.