(E)-4-methyl-N-styrylbenzamide

• 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-methyl-N-styrylbenzamide
• 英文别名: 4-methyl-N-[(E)-2-phenylethenyl]benzamide
• 化学式: C₁₆H₁₅NO
• 分子量: 237.301
• InChiKey: WMGSCYOPEAKCHI-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 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)-4-methyl-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72%的产率得到5-phenyl-2-p-tolyloxazole
  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：

  对甲苯酰胺 在 sodium hydride 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 12.0h， 生成 (E)-4-methyl-N-styrylbenzamide
  参考文献：
  名称：

  A Novel Route to N-Styrylamides

  摘要：

  A general synthesis of N-styrylamides starting from amides and phenylacetaldehyde is described. Condensation of the amide, aldehyde and benzotriazole affords N-(1-benzotriazol-1-yl-2-phenylethyl)amides 2 from which the benzotriazole molecule is smoothly eliminated.

  DOI：

  10.1080/00397919508012683

文献信息

• BETA-PHOSPHONYL-ENAMINE DERIVATIVE AND PREPARATION METHOD THEREFOR
  申请人：SOOCHOW UNIVERSITY

  公开号：US20210130377A1

  公开（公告）日：2021-05-06

  The present invention discloses the preparation method of β-phosphonyl-enamine derivative. The preparation method comprising the following steps: dissolving the enamine derivative, organic phosphine compound, manganese acetate and potassium carbonate in the solvent, reacting at room temperature to obtain the β-phosphonyl-enamine derivative. The enamine derivative was as the starting material, and the raw materials are easy to obtain and a great many varieties. The various forms of the products obtained therein can be directly applied and can be used in further reactions. The reaction conditions are mild, the reaction speed is high, the reaction operation and the post-treatment process are simple, the production is convenient, and the method is suitable for large-scale production.

  本发明公开了β-膦酰基-烯胺衍生物的制备方法。该制备方法包括以下步骤：在溶剂中溶解烯胺衍生物、有机膦化合物、醋酸锰和碳酸钾，室温下反应得到β-膦酰基-烯胺衍生物。烯胺衍生物作为起始物质，原料易得且种类繁多。所得产品的各种形式可以直接应用，并可用于进一步的反应中。反应条件温和，反应速度快，反应操作和后处理过程简单，生产方便，该方法适用于大规模生产。
• BETA-AMINO PHOSPHONIC ACID DERIVATIVE AND PREPARATION METHOD THEREFOR
  申请人：SOOCHOW UNIVERSITY

  公开号：US20210130376A1

  公开（公告）日：2021-05-06

  A method for preparing a β-amino phosphonic acid derivative includes: dissolving N-(arylvinyl)benzamide, dialkyl phosphite, manganese acetate, and potassium carbonate in a solvent and reacting at room temperature to obtain (2-benzamido-1-arylvinyl)dialkyl-phosphonate derivative; and hydrolyzing (2-benzamido-1-arylethyl) dialkylphosphonate derivative to obtain β-amino phosphonic acid derivative. The N-(arylvinyl) benzamide derivative is used as starting material. The raw materials are easy to obtain and are of many different types. A method of preparing β-aminophosphonic acid derivative includes: dissolving N-(arylvinyl)benzamide, dialkyl phosphite, manganese acetate and potassium carbonate in a solvent, reacting at room temperature to obtain (2-benzamide-1-arylvinyl) dialkyl phosphonate derivative, and then reducing and hydrolyzing the compound to obtain β-aminophosphonic acid derivative. The method of the invention has the advantages of short synthesis route, mild reaction conditions, simple reaction operation and post-treatment process, good yield, and is suitable for large-scale production.

  一种制备β-氨基膦酸衍生物的方法包括：将N-(芳基乙烯基)苯甲酰胺、二烷基膦酸酯、乙酸锰和碳酸钾溶解于溶剂中，在室温下反应以获得(2-苯甲酰胺-1-芳基乙烯基)二烷基膦酸酯衍生物; 然后水解(2-苯甲酰胺-1-芳基乙基)二烷基膦酸酯衍生物以获得β-氨基膦酸衍生物。N-(芳基乙烯基)苯甲酰胺衍生物用作起始材料。原材料易于获得且种类繁多。该发明的方法具有合成路线短、反应条件温和、反应操作和后处理过程简单、收率高、适合大规模生产等优点。
• Synthesis of Linear Enamides and Enecarbamates <i>via</i> Photoredox Acceptorless Dehydrogenation
  作者：Ritu、Daniel Kolb、Nidhi Jain、Burkhard König

  DOI：10.1002/adsc.202201259

  日期：2023.2.21

  decatungstate (TBADT) as hydrogen atom transfer (HAT) agent and a cobaloxime co-catalyst for dihydrogen evolution for the dehydrogenative preparation of linear enamides and enecarbamates from saturated precursors. The substrate scope includes several natural products and drug derivatives. The reaction does not require noble metal catalysts, exhibits short reaction times compared to previous methods and is suitable

  近年来，在光氧化还原和过渡金属催化的独特组合的推动下，开发了几种直接使脂肪族化合物去饱和的方法。因此，可以以简单的方式制备具有高功能化潜力的烯烃。我们采用了先前报道的系统，该系统涉及四丁基十钨酸铵 (TBADT) 作为氢原子转移 (HAT) 剂和用于从饱和前体脱氢制备线性烯酰胺和烯氨基甲酸酯的双氢析出的钴肟助催化剂。底物范围包括几种天然产物和药物衍生物。该反应不需要贵金属催化剂，与以往方法相比反应时间短，适用于药物衍生物的后期功能化。
• 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。
• A Novel Route to N-Styrylamides
  作者：A. R. Katritzky、A. V. Ignatchenko、H. Lang

  DOI：10.1080/00397919508012683

  日期：1995.4

  A general synthesis of N-styrylamides starting from amides and phenylacetaldehyde is described. Condensation of the amide, aldehyde and benzotriazole affords N-(1-benzotriazol-1-yl-2-phenylethyl)amides 2 from which the benzotriazole molecule is smoothly eliminated.