N-(2-iodophenyl)-N-methyl-6-heptenamide | 135190-55-5

• 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-iodophenyl)-N-methyl-6-heptenamide
• 英文别名: N-(2-iodophenyl)-N-methylhept-6-enamide
• CAS: 135190-55-5
• 化学式: C₁₄H₁₈INO
• 分子量: 343.208
• InChiKey: YIERPWVYTNHEPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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-(2-iodophenyl)-N-methyl-6-heptenamide 在 二甲基硫 、 偶氮二异丁腈 、 三正丁基氢锡 、 碳酸氢钠 、 臭氧 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 13.0h， 生成 cis-N-methyl-N-phenyl-2-benzylcyclopentanecarboxamide
  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：

  2-碘苯胺 在 氢氧化钾 、 三氯溴甲烷 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 8.5h， 生成 N-(2-iodophenyl)-N-methyl-6-heptenamide
  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

• Cobalt-catalyzed chemoselective dehydrogenation through radical translocation under visible light
  作者：Wan-Lei Yu、Zi-Gang Ren、Ke-Xing Ma、Hui-Qing Yang、Jun-Jie Yang、Haixue Zheng、Wangsuo Wu、Peng-Fei Xu

  DOI：10.1039/d2sc02291e

  日期：——

  corresponding saturated counterparts by the dehydrogenative strategy are a dream reaction that has remained largely underexplored. In this report, a straightforward and robust cobaloxime-catalyzed photochemical dehydrogenation strategy via intramolecular HAT is described for the first time. The reaction proceeds through an intramolecular radical translocation followed by the cobalt assisted dehydrogenation without

  通过脱氢策略从相应的饱和对应物中直接去除氢的转变是一个梦想的反应，但在很大程度上仍未得到充分探索。在本报告中，首次描述了一种通过分子内 HAT 的简单而稳健的钴肟催化光化学脱氢策略。该反应通过分子内自由基易位进行，然后进行钴辅助脱氢，不需要任何其他外部光敏剂、贵金属或氧化剂。通过这种方法，以中等至优异的产率获得了一系列有价值的不饱和化合物，例如α，β-不饱和酰胺、烯酰胺以及烯丙型和高烯丙型磺酰胺，具有良好的化学和区域选择性，并且通过一系列转化证明了合成的多功能性。并讨论了该方法的机理研究。
• 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.