(E)-2-styryl-5-(trifluoromethyl)benzamide | 1268451-37-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-2-styryl-5-(trifluoromethyl)benzamide
• 英文别名: 2-[(E)-2-phenylethenyl]-5-(trifluoromethyl)benzamide
• CAS: 1268451-37-1
• 化学式: C₁₆H₁₂F₃NO
• 分子量: 291.273
• InChiKey: GMWBVRCVSOOFFG-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 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：
  43.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(三氟甲基)苯甲酰氯 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 cesium acetate 、 potassium carbonate 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 32.0h， 生成 (E)-2-styryl-5-(trifluoromethyl)benzamide
  参考文献：
  名称：

  Rh(III)-Catalyzed Directed C−H Olefination Using an Oxidizing Directing Group: Mild, Efficient, and Versatile

  摘要：

  An efficient Rh(III)-catalyzed oxidative olefination by directed C-H bond activation of N-methoxybenzamides is reported. In this mild, practical, selective, and high-yielding process, the N-O bond acts as an internal oxidant. In addition, simply changing the substituent of the directing/oxidizing group results in the selective formation of valuable tetrahydroisoquinolinone products.

  DOI：

  10.1021/ja109676d

文献信息

• Rhodium-Catalyzed Oxidative Olefination of CH Bonds in Acetophenones and Benzamides
  作者：Frederic W. Patureau、Tatiana Besset、Frank Glorius

  DOI：10.1002/anie.201006222

  日期：2011.2.1

  A good neighborhood! The metal‐catalyzed oxidative CH functionalization of electron‐rich arenes is well‐established, but analogous reactions of electron‐poor substrates are rare. A new application makes use of common electron‐withdrawing functional groups (COMe, CONH2, CONEt2) in the rhodium‐catalyzed oxidative Heck reaction to generate complex organic molecules. Cp*= η5‐C5Me5.

  好邻居！富电子芳烃的金属催化氧化CH官能化是公认的，但贫电子底物的类似反应很少见。一项新的应用在铑催化的氧化Heck反应中利用了常见的吸电子官能团（COMe，CONH 2，CONEt 2）来生成复杂的有机分子。的Cp * =η 5 -C 5我5。
• Rh(III)-Catalyzed Directed C−H Olefination Using an Oxidizing Directing Group: Mild, Efficient, and Versatile
  作者：Souvik Rakshit、Christoph Grohmann、Tatiana Besset、Frank Glorius

  DOI：10.1021/ja109676d

  日期：2011.3.2

  An efficient Rh(III)-catalyzed oxidative olefination by directed C-H bond activation of N-methoxybenzamides is reported. In this mild, practical, selective, and high-yielding process, the N-O bond acts as an internal oxidant. In addition, simply changing the substituent of the directing/oxidizing group results in the selective formation of valuable tetrahydroisoquinolinone products.