(E)-N-tosylhex-2-enamide | 1017582-07-8

• 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-tosylhex-2-enamide
• 英文别名: (E)-N-(4-methylphenyl)sulfonylhex-2-enamide
• CAS: 1017582-07-8
• 化学式: C₁₃H₁₇NO₃S
• 分子量: 267.349
• InChiKey: OUANXKXMRLTEQZ-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  71.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-已烯醛 、 chloroamine-T 在 吡啶 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以62%的产率得到(E)-N-tosylhex-2-enamide
  参考文献：
  名称：

  实用的铜（I）催化的醛化酰胺化反应。

  摘要：

  通过插入廉价的，容易获得的由卤化铜（i）和吡啶原位生成的催化剂，表明通过插入醛的CH键直接合成酰胺是一种实用的方法。

  DOI：

  10.1039/b918588g

文献信息

• Iron(II)-Catalyzed Amidation of Aldehydes with Iminoiodinanes at Room Temperature and under Microwave-Assisted Conditions
  作者：Thi My Uyen Ton、Ciputra Tejo、Stefani Tania、Joyce Wei Wei Chang、Philip Wai Hong Chan

  DOI：10.1021/jo200284a

  日期：2011.6.17

  A method for the amidation of aldehydes with PhI=NTs/PhI=NNs as the nitrogen source and an inexpensive iron(II) chloride + pyridine as the in situ formed precatalyst under mild conditions at room temperature or microwave assisted conditions is described. The reaction was operationally straightforward and accomplished in moderate to excellent product yields (20-99%) and with complete chemoselectivity with the new C-N bond forming only at the formylic C-H bond in substrates containing other reactive functional groups. By utilizing microwave irradiation, comparable product yields and short reaction times of 1 h could be accomplished. The mechanism is suggested to involve insertion of a putative iron-nitrene/imido group to the formylic C H bond of the substrate via a H-atom abstraction/radical rebound pathway mediated by the precatalyst [Fe(py)(4)Cl-2] generated in situ from reaction of FeCl2 with pyridine.
• Highly Efficient Ruthenium(II) Porphyrin Catalyzed Amidation of Aldehydes
  作者：Joyce Wei Wei Chang、Philip Wai Hong Chan

  DOI：10.1002/anie.200704695

  日期：2008.1.25
• Practical copper(i)-catalysed amidation of aldehydes
  作者：Joyce Wei Wei Chang、Thi My Uyen Ton、Stefani Tania、Paul C. Taylor、Philip Wai Hong Chan

  DOI：10.1039/b918588g

  日期：——

  The direct synthesis of amides by insertion into the C-H bond of aldehydes is shown to be a practical procedure through application of cheap, readily available catalysts generated in situ from copper(i) halides and pyridine.

  通过插入廉价的，容易获得的由卤化铜（i）和吡啶原位生成的催化剂，表明通过插入醛的CH键直接合成酰胺是一种实用的方法。