(E)-4-nitro-N-styrylbenzamide | 1393689-80-9

• 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)-4-nitro-N-styrylbenzamide
• 英文别名: 4-nitro-N-[(E)-2-phenylethenyl]benzamide
• CAS: 1393689-80-9
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: CVXREJIYXRCQKI-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  20
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-4-nitro-N-styrylbenzamide 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22%的产率得到2-(4-nitro-phenyl)-5-phenyl-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：

  [(Z)-2-溴乙烯基]苯 、 对硝基苯甲酰胺 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38%的产率得到(E)-4-nitro-N-styrylbenzamide
  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。
• Rhodium(III)-Catalyzed Cross-Coupling of Alkenylboronic Acids and <i>N</i>-Pivaloyloxylamides
  作者：Chao Feng、Teck-Peng Loh

  DOI：10.1021/ol501309e

  日期：2014.7.3

  Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydroboration, it enables the formal anti-Markovnikov hydroamidation of terminal alkynes, stereospecifically affording the trans-enamides in excellent yields.
• 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.