(E)-N-styrylthiophene-2-carboxamide | 1393689-93-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: (E)-N-styrylthiophene-2-carboxamide
• 英文别名: N-[(E)-2-phenylethenyl]thiophene-2-carboxamide
• CAS: 1393689-93-4
• 化学式: C₁₃H₁₁NOS
• 分子量: 229.302
• InChiKey: PVMSPFYROJGZNJ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  57.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-styrylthiophene-2-carboxamide 在 dipotassium peroxodisulfate 、 烟酸乙酯 、 四丁基溴化铵 、 copper(ll) bromide 作用下， 以 乙腈 为溶剂， 反应 24.0h， 以47%的产率得到5-phenyl-2-(thiophene-2-yl)oxazole
  参考文献：
  名称：

  Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization

  摘要：

  A copper(11)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.

  DOI：

  10.1021/jo301332s
• 作为产物：
  描述：

  2-噻吩甲酰胺 、 [(Z)-2-溴乙烯基]苯 在 copper(l) iodide 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以62%的产率得到(E)-N-styrylthiophene-2-carboxamide
  参考文献：
  名称：

  Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization

  摘要：

  A copper(11)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.

  DOI：

  10.1021/jo301332s

文献信息

• Decarboxylative Enamide Synthesis from Carboxylic Acid and Alkenyl Isocyanate
  作者：Rui Wang、Wenbo H. Liu

  DOI：10.1021/acs.orglett.3c01682

  日期：2023.7.21

  protocol to access the enamide via employing carboxylic acid and alkenyl isocyanate as the precursors promoted by DMAP without involving any metal catalysts and dehydration reagents. This protocol is simple and practical and tolerates numerous functional groups. Considering the simplicity, the ready availability of both starting materials, and the significance of the enamides, we expect that this reaction

  在此，我们报道了一种通过使用羧酸和烯基异氰酸酯作为 DMAP 促进的前体来获取烯酰胺的方案，而不涉及任何金属催化剂和脱水试剂。该协议简单实用，并且能够容忍多种官能团。考虑到简单性、两种起始材料的现成性以及烯酰胺的重要性，我们预计该反应将得到广泛的应用。
• Room Temperature Copper(II)-Catalyzed Oxidative Cyclization of Enamides to 2,5-Disubstituted Oxazoles via Vinylic C–H Functionalization
  作者：Chi Wai Cheung、Stephen L. Buchwald

  DOI：10.1021/jo301332s

  日期：2012.9.7

  A copper(11)-catalyzed oxidative cyclization of enamides to oxazoles via vinylic C-H bond functionalization at room temperature is described. Various 2,5-disubstituted oxazoles bearing aryl, vinyl, alkyl, and heteroaryl substituents could be synthesized in moderate to high yields. This reaction protocol is complementary to our previously reported iodine-mediated cyclization of enamides to afford 2,4,5-trisubstituted oxazoles.