N-(2-phenylethynyl)-N-4-methoxybenzenesulfonylbutanamine | 1160723-36-3

• 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-(2-phenylethynyl)-N-4-methoxybenzenesulfonylbutanamine
• 英文别名: N-butyl-4-methoxy-N-(2-phenylethynyl)benzenesulfonamide
• CAS: 1160723-36-3
• 化学式: C₁₉H₂₁NO₃S
• 分子量: 343.447
• InChiKey: DKGFGNPNZXRXHH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-phenylethynyl)-N-4-methoxybenzenesulfonylbutanamine 、 烯丙醇 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以88.889%的产率得到
  参考文献：
  名称：

  Stereoselective Synthesis of (2Z)-2,4-Dienamides via NBS-Mediated Allyloxyl Addition–Claisen Rearrangement–Dehydrobromination Cascade Reaction of Ynsulfonamides

  摘要：

  An NBS-promoted allyloxyl addition-Claisen reatrangement-dehydrobtomination cascade reaction has been developed. More than 20 substituted alkynylsulfonamides were reacted with allyl alcohols to generate (2Z)-2,4-dienamides in moderate to high yields. A mechanistic model has been proposed to account for the overall reaction sequence including the stereochemical outcome. Theoretical calculations suggested that a [3,3] sigmatropic rearrangement be the rate-limiting step.

  DOI：

  10.1021/acs.orglett.5b01859
• 作为产物：
  描述：

  N-butyl-4-methoxybenzenesulfonamide 、 苯基溴乙炔 在 iron(III) chloride hexahydrate 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以96%的产率得到N-(2-phenylethynyl)-N-4-methoxybenzenesulfonylbutanamine
  参考文献：
  名称：

  Iron-Catalyzed Amidation of Alkynyl Bromides: A Facile Route for the Preparation of Ynamides

  摘要：

  A facile route to obtain ynamides in high yields was described. The products were achieved through the iron-catalyzed C-N coupling reaction of amides with alkynyl bromides in the presence of 20 mol % of N,N'-dimethylethane-1,2-diamine (DMEDA).

  DOI：

  10.1021/jo900595c

文献信息

• Stereoselective Synthesis of (2<i>Z</i>)-2,4-Dienamides via NBS-Mediated Allyloxyl Addition–Claisen Rearrangement–Dehydrobromination Cascade Reaction of Ynsulfonamides
  作者：Runbo Ding、Yun Li、Cheng Tao、Bin Cheng、Hongbin Zhai

  DOI：10.1021/acs.orglett.5b01859

  日期：2015.8.21

  An NBS-promoted allyloxyl addition-Claisen reatrangement-dehydrobtomination cascade reaction has been developed. More than 20 substituted alkynylsulfonamides were reacted with allyl alcohols to generate (2Z)-2,4-dienamides in moderate to high yields. A mechanistic model has been proposed to account for the overall reaction sequence including the stereochemical outcome. Theoretical calculations suggested that a [3,3] sigmatropic rearrangement be the rate-limiting step.
• Iron-Catalyzed Amidation of Alkynyl Bromides: A Facile Route for the Preparation of Ynamides
  作者：Bangben Yao、Zunjun Liang、Tianmin Niu、Yuhong Zhang

  DOI：10.1021/jo900595c

  日期：2009.6.19

  A facile route to obtain ynamides in high yields was described. The products were achieved through the iron-catalyzed C-N coupling reaction of amides with alkynyl bromides in the presence of 20 mol % of N,N'-dimethylethane-1,2-diamine (DMEDA).