N-(o-iodophenyl)-N-methyl-3,7-dimethyl-6-octenamide | 135190-65-7

• 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: N-(o-iodophenyl)-N-methyl-3,7-dimethyl-6-octenamide
• 英文别名: N-(2-iodophenyl)-N,3,7-trimethyloct-6-enamide
• CAS: 135190-65-7
• 化学式: C₁₇H₂₄INO
• 分子量: 385.288
• InChiKey: GBUAQXOFKDISBT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  N-(o-iodophenyl)-N-methyl-3,7-dimethyl-6-octenamide 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 苯 为溶剂， 反应 8.0h， 以84%的产率得到N-methyl-N-phenyl-5-isopropyl-2-methylcyclopentanecarboxamide
  参考文献：
  名称：

  Amide-based protecting/radical translocating (PRT) groups. Generation of radicals adjacent to carbonyls by 1,5-hydrogen transfer reactions of o-iodoanilides

  摘要：

  The o-iodoanilide group is shown to be broadly useful for the generation and subsequent reactions of radicals adjacent to carboxyl groups. The results indicate that this group is one of the best ''protecting/radical translocating'' (PRT) groups introduced to date. Beyond its good performance in radical translocation reactions, it is easy to introduce, serves as a reasonable protecting group both before and after the translocation, and (with appropriate modifications) is easy to remove.

  DOI：

  10.1016/s0040-4020(01)90466-1
• 作为产物：
  描述：

  N-(2-iodophenyl)-3,7-dimethyloct-6-enamide 、 碘甲烷 在 氢氧化钾 作用下， 生成 N-(o-iodophenyl)-N-methyl-3,7-dimethyl-6-octenamide
  参考文献：
  名称：

  Amide-based protecting/radical translocating (PRT) groups. Generation of radicals adjacent to carbonyls by 1,5-hydrogen transfer reactions of o-iodoanilides

  摘要：

  The o-iodoanilide group is shown to be broadly useful for the generation and subsequent reactions of radicals adjacent to carboxyl groups. The results indicate that this group is one of the best ''protecting/radical translocating'' (PRT) groups introduced to date. Beyond its good performance in radical translocation reactions, it is easy to introduce, serves as a reasonable protecting group both before and after the translocation, and (with appropriate modifications) is easy to remove.

  DOI：

  10.1016/s0040-4020(01)90466-1

文献信息

• Radical translocation reactions of o-iodoanilides: the use of carbon-hydrogen bonds as precursors of radicals adjacent to carbonyl groups
  作者：Dennis P. Curran、Ann C. Abraham、Hongtao Liu

  DOI：10.1021/jo00014a001

  日期：1991.7

  The treatment of o-iodoanilides with tributyltin hydride results in radical generation followed by rapid translocation to produce radicals adjacent to carbonyls. These radicals participate in cyclization and asymmetric addition reactions.