3-butoxy-3-(toluene-4-sulfonylimino)propionic acid ethyl ester | 1327166-12-0

• 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: 3-butoxy-3-(toluene-4-sulfonylimino)propionic acid ethyl ester
• 英文别名: Ethyl 3-butoxy-3-(4-methylphenyl)sulfonyliminopropanoate；ethyl 3-butoxy-3-(4-methylphenyl)sulfonyliminopropanoate
• CAS: 1327166-12-0
• 化学式: C₁₆H₂₃NO₅S
• 分子量: 341.428
• InChiKey: MXZZCUNHAPUAEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  90.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对甲苯磺酰叠氮 、 丙炔酸乙酯 、 正丁醇 在 copper(II) acetate monohydrate 、 2-氨基苯酚 作用下， 反应 0.17h， 以95%的产率得到3-butoxy-3-(toluene-4-sulfonylimino)propionic acid ethyl ester
  参考文献：
  名称：

  Highly controlling selectivity of copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) between sulfonyl azids and normal alkynes or propynoates

  摘要：

  In this article, a combination of Cu(OAc)(2).H(2)O/(2)-aminophenol was developed as a highly efficient and controlling catalytic system for sulfonyl azids involved CuAAC. By using this catalytic system, sulfonyl azids reacted with normal alkynes or propynoates to selectively give the ring products or the chain products, respectively, in excellent yields within minutes. HOAc in situ produced in the reaction has been proved to be a super protonation reagent, by which the unstable intermediate 5-cuprated 1,2,3-triazole was protonated efficiently to yield ring-product 1-sulfonyl 1,2,3-trizoles. The control experiments also proved that 2-aminophenol played dual roles as both ligand and reductant, which led to the cheap and chemically stable Cu(OAc)(2)center dot H(2)O being an efficient copper source for our purpose. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.017

文献信息

• Highly controlling selectivity of copper(I)-catalyzed azide/alkyne cycloaddition (CuAAC) between sulfonyl azids and normal alkynes or propynoates
  作者：Yantao Liu、Xinyan Wang、Jimin Xu、Qun Zhang、Yi Zhao、Yuefei Hu

  DOI：10.1016/j.tet.2011.06.017

  日期：2011.8

  In this article, a combination of Cu(OAc)(2).H(2)O/(2)-aminophenol was developed as a highly efficient and controlling catalytic system for sulfonyl azids involved CuAAC. By using this catalytic system, sulfonyl azids reacted with normal alkynes or propynoates to selectively give the ring products or the chain products, respectively, in excellent yields within minutes. HOAc in situ produced in the reaction has been proved to be a super protonation reagent, by which the unstable intermediate 5-cuprated 1,2,3-triazole was protonated efficiently to yield ring-product 1-sulfonyl 1,2,3-trizoles. The control experiments also proved that 2-aminophenol played dual roles as both ligand and reductant, which led to the cheap and chemically stable Cu(OAc)(2)center dot H(2)O being an efficient copper source for our purpose. (C) 2011 Elsevier Ltd. All rights reserved.