m-nitrobenzoic acid (E)-styryl amide

• 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: m-nitrobenzoic acid (E)-styryl amide
• 英文别名: (E)-3-nitro-N-styrylbenzamide；3-nitro-N-[(E)-2-phenylethenyl]benzamide
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: XKPIUOUDSDNUTP-MDZDMXLPSA-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：

  m-nitrobenzoic acid (E)-styryl amide 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44%的产率得到2-(3-nitrophenyl)-5-phenyloxazole
  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)-β-phenylepoxyethyltrimethylsilane 在 lithium aluminium tetrahydride 、 sodium azide 、 potassium tert-butylate 、 氯化铵 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 水 为溶剂， 生成 m-nitrobenzoic acid (E)-styryl amide
  参考文献：
  名称：

  Stereoselective Synthesis of Enamides by a Peterson Reaction Manifold

  摘要：

  [GRAPHICS]Vinylsilanes are converted into enamides by a sequence comprising epoxidation, nucleophilic ring opening of the resulting epoxysilanes with NaN3, and reduction of the azide, followed by a "one-pot" N-acylation/Peterson elimination process. This method is distinguished by its wide applicability and stereoselective course.

  DOI：

  10.1021/ol016848p

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.
• Iodine(III)-Promoted Synthesis of Oxazoles through Oxidative Cyclization of N-Styrylbenzamides
  作者：Boris Nachtsheim、Christian Hempel

  DOI：10.1055/s-0033-1339491

  日期：——

  The hypervalent iodine reagent PhI(OTf)(2), generated in situ, has been successfully utilized in an intramolecular oxidative cyclization of N-styrylbenzamides. In remarkably short reaction times, the desired 2,5-disubstituted oxazoles were isolated in high yields in this metal-free oxidative C-O bond-forming reaction.
• Stereoselective Synthesis of Enamides by a Peterson Reaction Manifold
  作者：Alois Fürstner、Christof Brehm、Yolanda Cancho-Grande

  DOI：10.1021/ol016848p

  日期：2001.11.1

  [GRAPHICS]Vinylsilanes are converted into enamides by a sequence comprising epoxidation, nucleophilic ring opening of the resulting epoxysilanes with NaN3, and reduction of the azide, followed by a "one-pot" N-acylation/Peterson elimination process. This method is distinguished by its wide applicability and stereoselective course.