(E)-N-styrylcyclohexanecarboxamide

• 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)-N-styrylcyclohexanecarboxamide
• 英文别名: N-[(E)-2-phenylethenyl]cyclohexanecarboxamide
• 化学式: C₁₅H₁₉NO
• 分子量: 229.322
• InChiKey: WGOHKZWVQSZVSR-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-styrylcyclohexanecarboxamide 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54%的产率得到2-cyclohexyl-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 (E)-N-styrylcyclohexanecarboxamide
  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

• 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。
• 10.1039/d4gc01238k
  作者：Yang, Guoqing、Jia, Jingpei、Zhu, Zile、Qiu, Youai

  DOI：10.1039/d4gc01238k

  日期：——

  Herein, a selective and efficient CO2-mediated Z to E isomerization of enamides is reported. Notably, CO2 acts as a promoter to form the key reaction intermediate. This protocol provides a novel method for the selective isomerization of enamides under mild conditions with moderate to excellent yields. The method exhibits a broad substrate scope, including late-stage modification of biorelevant molecules

  在此，报道了烯酰胺的选择性且有效的CO 2介导的Z至E异构化。值得注意的是，CO 2充当形成关键反应中间体的促进剂。该方案提供了一种在温和条件下选择性异构化烯酰胺的新方法，具有中等至优异的产率。该方法具有广泛的底物范围，包括生物相关分子的后期修饰。通过循环伏安法 (CV) 和密度泛函理论 (DFT) 计算得出的机理见解提供了证据，证明中间体通过非常规的 C 中心模式促进了反应。
• 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.
• 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.