(E)-N-(2-methylstyryl)-2-naphthamide | 1393689-87-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-N-(2-methylstyryl)-2-naphthamide
• 英文别名: N-[(E)-2-(2-methylphenyl)ethenyl]naphthalene-2-carboxamide
• CAS: 1393689-87-6
• 化学式: C₂₀H₁₇NO
• 分子量: 287.361
• InChiKey: MLOFYZXBCWEPTG-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-(2-methylstyryl)-2-naphthamide 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78%的产率得到2-(naphthalen-2-yl)-5-(o-tolyl)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：

  (E)-3-(2-甲基苯基)丙-2-烯酸 在 N-溴代丁二酰亚胺(NBS) 、 copper(l) iodide 、 manganese (II) acetate tetrahydrate 、 potassium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 (E)-N-(2-methylstyryl)-2-naphthamide
  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

• 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.