(Z)-3-((4-acetylphenyl)(phenyl)methylene)-1-methylindolin-2-one | 1039396-08-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (Z)-3-((4-acetylphenyl)(phenyl)methylene)-1-methylindolin-2-one
• 英文别名: (3Z)-3-[(4-acetylphenyl)-phenylmethylidene]-1-methylindol-2-one
• CAS: 1039396-08-1
• 化学式: C₂₄H₁₉NO₂
• 分子量: 353.42
• InChiKey: ACUUPQMJHXEUOB-FCQUAONHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-(4-acetylphenyl)-N-methyl-N-phenylpropiolamide 、 苯 在 silver(I) acetate 、 palladium diacetate 、 三苯基膦 作用下， 反应 24.0h， 以56%的产率得到(Z)-3-((4-acetylphenyl)(phenyl)methylene)-1-methylindolin-2-one
  参考文献：
  名称：

  Selective Synthesis of 3-Aryl Quinolin-2(1H)-ones and 3-(1-Arylmethylene)oxindoles Involving a 2-Fold Arene C−H Activation Process

  摘要：

  A novel and selective palladium-catalyzed C-H activation protocol has been developed for the synthesis of 3-aryl quinolin-2(1H)-ones and 3-(1-arylmethylene)oxindoles with use of PivOH as the switch. In the presence of Pd(OAc)(2), AgOAc, and PivOH, a variety or N-methyl anilides reacted with arenes to afford the corresponding 3-aryl quinolin-2(l H)-ones in moderate yields, whereas the selectivity was shifted toward 3-(1-arylmethylene)oxindoles in the absence of PivOH.

  DOI：

  10.1021/jo901314t

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.
• Palladium-Catalyzed C−H Functionalization of <i>N</i>-Arylpropiolamides with Aryliodonium Salts: Selective Synthesis of 3-(1-Arylmethylene)oxindoles
  作者：Shi Tang、Peng Peng、Ping Zhong、Jin-Heng Li

  DOI：10.1021/jo8008808

  日期：2008.7.1

  A selective and efficient method for the synthesis of 3-(1-arylmethylene)oxindoles by palladium-catalyzed C-H functionalization of anilides with aryliodonium salts has been developed. In the presence of Pd(OAc)(2) and Et3N, a variety of anilides underwent the reaction with aryliodonium salts to afford the corresponding 3-(1-arylmethylene)oxindoles in moderate to good yields. It is noteworthy that the reaction can be conducted providing moderate yields even without bases. The mechanism of the reaction was also discussed.