(E)-N-(2-iodophenyl)-2-methyl-3-phenylacrylamide | 1390630-95-1

• 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)-2-methyl-3-phenylacrylamide
• CAS: 1390630-95-1
• 化学式: C₁₆H₁₄INO
• 分子量: 363.198
• InChiKey: NXJLZXXWMGVDRT-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 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：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (E)-N-(2-iodophenyl)-2-methyl-3-phenylacrylamide 在 四(三苯基膦)钯 、 sodium hydride 、 caesium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 mineral oil 为溶剂， 反应 0.67h， 生成 (RS)-1,3-dimethyl-3-((RS)-1-phenylallyl)indolin-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-碘苯胺 、 ethyl (E)-2-methyl-3-phenyl-2-propenoate 在 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 0.67h， 以87%的产率得到(E)-N-(2-iodophenyl)-2-methyl-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