(E)-N-(2-iodophenyl)-N,2-dimethyl-3-phenylacrylamide | 1390630-90-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-(2-iodophenyl)-N,2-dimethyl-3-phenylacrylamide
• 英文别名: (E)-N-(2-iodophenyl)-N,2-dimethyl-3-phenylprop-2-enamide
• CAS: 1390630-90-6
• 化学式: C₁₇H₁₆INO
• 分子量: 377.225
• InChiKey: XQCJPPXAZZCTFU-OUKQBFOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-N-(2-iodophenyl)-N,2-dimethyl-3-phenylacrylamide 、 苯硼酸频哪醇酯 在 四(三苯基膦)钯 、 caesium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 以94%的产率得到3-benzhydryl-1,3-dimethylindolin-2-one
  参考文献：
  名称：

  Domino Carbopalladation–Cross-Coupling for the Synthesis of 3,3-Disubstituted Oxindoles

  摘要：

  This study examines a domino carbopalladation-cross-coupling reaction for the formation of valuable oxindole scaffolds. Furthermore, the reaction sequence forges vicinal stereocenters In a stereospecific manner through the formation of two carbon carbon bonds and, thereby, rapidly generates complexity. The reaction gives high yields for a variety of acrylamide substrates, and various organoboranes have also been evaluated for the cross-coupling. This work offers insight into the relative rates determining a successful carbopalladation-cross-coupling reaction and how to favor the desired reaction pathway.

  DOI：

  10.1021/ol301539p
• 作为产物：
  描述：

  2-甲基-3-苯基丙烯酸 在 草酰氯 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 (E)-N-(2-iodophenyl)-N,2-dimethyl-3-phenylacrylamide
  参考文献：
  名称：

  Domino Carbopalladation–Cross-Coupling for the Synthesis of 3,3-Disubstituted Oxindoles

  摘要：

  This study examines a domino carbopalladation-cross-coupling reaction for the formation of valuable oxindole scaffolds. Furthermore, the reaction sequence forges vicinal stereocenters In a stereospecific manner through the formation of two carbon carbon bonds and, thereby, rapidly generates complexity. The reaction gives high yields for a variety of acrylamide substrates, and various organoboranes have also been evaluated for the cross-coupling. This work offers insight into the relative rates determining a successful carbopalladation-cross-coupling reaction and how to favor the desired reaction pathway.

  DOI：

  10.1021/ol301539p

文献信息

• Palladium-Catalyzed Heck-type Domino Cyclization and Carboxylation to Synthesize Carboxylic Acids by Utilizing Chloroform as the Carbon Monoxide Source
  作者：Xianglei Liu、Bin Li、Zhenhua Gu

  DOI：10.1021/acs.joc.5b01126

  日期：2015.8.7

  A palladium-catalyzed domino cyclization and carboxylation reaction for synthesis of a variety of carboxylic acids was developed, where chloroform was used as “carbon monoxide” source. The in situ generated neopentylpalladium species by Heck cyclization was efficiently trapped by dichlorocarbene to form a series of carboxylic acids. It was found that in this type of domino reaction CHCl3 is a convenient

  开发了钯催化的多米诺环化和羧化反应以合成多种羧酸，其中氯仿用作“一氧化碳”来源。通过Heck环化原位产生的新戊基钯物质被二氯卡宾有效地捕获以形成一系列羧酸。已经发现，在这种类型的多米诺反应中，CHCl 3是用于CO气体的方便且安全的替代物。