(E)-N-styryl-4-(trifluoromethyl)benzamide | 1393689-79-6

• 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-styryl-4-(trifluoromethyl)benzamide
• 英文别名: N-[(E)-2-phenylethenyl]-4-(trifluoromethyl)benzamide
• CAS: 1393689-79-6
• 化学式: C₁₆H₁₂F₃NO
• 分子量: 291.273
• InChiKey: NACZITSXEYOUJW-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 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：
  4

反应信息

• 作为反应物：
  描述：

  (E)-N-styryl-4-(trifluoromethyl)benzamide 在 三氟甲磺酸三甲基硅酯 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 以77%的产率得到5-phenyl-2-(4-(trifluoromethyl)phenyl)oxazole
  参考文献：
  名称：

  Iodine(III)-Promoted Synthesis of Oxazoles through Oxidative Cyclization of N-Styrylbenzamides

  摘要：

  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.

  DOI：

  10.1055/s-0033-1339491
• 作为产物：
  描述：

  4-(三氟甲基)苯甲酰胺 在 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲苯 、 mineral oil 为溶剂， 反应 24.0h， 生成 (E)-N-styryl-4-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Iodine(III)-Promoted Synthesis of Oxazoles through Oxidative Cyclization of N-Styrylbenzamides

  摘要：

  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.

  DOI：

  10.1055/s-0033-1339491

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。
• 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.
• 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.
• 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.