N-(2-bromo-5-(trifluoromethyl)phenyl)propiolamide | 1477484-83-5

• 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: N-(2-bromo-5-(trifluoromethyl)phenyl)propiolamide
• 英文别名: N-[2-bromo-5-(trifluoromethyl)phenyl]prop-2-ynamide
• CAS: 1477484-83-5
• 化学式: C₁₀H₅BrF₃NO
• 分子量: 292.055
• InChiKey: QMQHGRJPAXYDTD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  N-(2-bromo-5-(trifluoromethyl)phenyl)propiolamide 在 copper(l) iodide 、 四(三苯基膦)钯 、 sodium acetate 、 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 31.5h， 生成 3-(diphenylmethylene)-1-methyl-6-(trifluoromethyl)indolin-2-one
  参考文献：
  名称：

  Synthesis of 3-(Diarylmethylene)oxindoles via a Palladium-Catalyzed One-Pot Reaction: Sonogashira-Heck-Suzuki-Miyaura Combined Reaction

  摘要：

  A novel one-pot reaction for the synthesis of 3-(diarylmethylene)oxindoles is described. The reaction involves the successive combination of three palladium-catalyzed reactions (Sonogashira, Heck, and Suzuki-Miyaura reactions). This method enables the rapid synthesis of various 3-(diarylmethylene)oxindoles from simple propiolamides. The addition of silver salts dramatically enhanced the E/Z stereoselectivity of the reaction.

  DOI：

  10.1055/s-0033-1339690
• 作为产物：
  描述：

  2-溴-5-三氟甲苯苯胺 、 丙炔酸 在 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以92%的产率得到N-(2-bromo-5-(trifluoromethyl)phenyl)propiolamide
  参考文献：
  名称：

  Synthesis of 3-(Diarylmethylene)oxindoles via a Palladium-Catalyzed One-Pot Reaction: Sonogashira-Heck-Suzuki-Miyaura Combined Reaction

  摘要：

  A novel one-pot reaction for the synthesis of 3-(diarylmethylene)oxindoles is described. The reaction involves the successive combination of three palladium-catalyzed reactions (Sonogashira, Heck, and Suzuki-Miyaura reactions). This method enables the rapid synthesis of various 3-(diarylmethylene)oxindoles from simple propiolamides. The addition of silver salts dramatically enhanced the E/Z stereoselectivity of the reaction.

  DOI：

  10.1055/s-0033-1339690

文献信息

• Synthesis of 3-(Diarylmethylene)oxindoles via a Palladium-Catalyzed One-Pot Reaction: Sonogashira-Heck-Suzuki-Miyaura Combined Reaction
  作者：Jae Seo、Guang Dong、Sunhwa Park、Dahye Lee、Kye Shin

  DOI：10.1055/s-0033-1339690

  日期：——

  A novel one-pot reaction for the synthesis of 3-(diarylmethylene)oxindoles is described. The reaction involves the successive combination of three palladium-catalyzed reactions (Sonogashira, Heck, and Suzuki-Miyaura reactions). This method enables the rapid synthesis of various 3-(diarylmethylene)oxindoles from simple propiolamides. The addition of silver salts dramatically enhanced the E/Z stereoselectivity of the reaction.