N-(cyclohex-1-enyl)-N-[(2-iodo-4,5-methylenedioxy)benzyl]-2-iodoacetamide | 454693-40-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: N-(cyclohex-1-enyl)-N-[(2-iodo-4,5-methylenedioxy)benzyl]-2-iodoacetamide
• 英文别名: N-(cyclohexen-1-yl)-2-iodo-N-[(6-iodo-1,3-benzodioxol-5-yl)methyl]acetamide
• CAS: 454693-40-4
• 化学式: C₁₆H₁₇I₂NO₃
• 分子量: 525.125
• InChiKey: VIXAVZLHGSGWLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(cyclohex-1-enyl)-N-[(2-iodo-4,5-methylenedioxy)benzyl]-2-iodoacetamide 在 N,N-azobis(cyclohexanecarbonitrile) 、 三正丁基氢锡 、 三正丁基氟化锡 作用下， 以 苯 为溶剂， 反应 10.0h， 以29%的产率得到9,10-(methylenedioxy)-<3a-(3aα,11bβ,11cα)>-2,3,3a,4,5,7,11b,11c-octahydro-1H-pyrrolo-<3,2,1-d,e>phenanthridin-5-one
  参考文献：
  名称：

  Is an Iodine Atom Almighty as a Leaving Group for Bu₃SnH-Mediated Radical Cyclization? The Effect of a Halogen Atom on the 5-Endo-trig Radical Cyclization of N-Vinyl-α-halo Amides

  摘要：

  The effect of a halogen atom as a leaving group on Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-l-enyl) alpha-halo amides was examined. The cyclization of alpha-chloro amides occurred with a high degree of efficiency, whereas the corresponding alpha-iodo congeners gave only limited quantities of cyclization products. A detailed study revealed that these phenomena could be attributed to the initial conformations of alpha-halo amides. The cyclizing ability of alpha-iodo amides can be restored with Bu3SnCl or Bu3SnF as an additive. The cyclization of an alpha-iodo amide in the presence of Bu3SnF could be applied to a short-step synthesis of lycoranes featuring sequential 5-endo-trig and 6-endo-trig radical cyclizations.

  DOI：

  10.1021/jo020007u
• 作为产物：
  描述：

  2-iodo-4,5-(methylenedioxy)benzylamine 在 三乙胺 、 sodium iodide 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 N-(cyclohex-1-enyl)-N-[(2-iodo-4,5-methylenedioxy)benzyl]-2-iodoacetamide
  参考文献：
  名称：

  Is an Iodine Atom Almighty as a Leaving Group for Bu₃SnH-Mediated Radical Cyclization? The Effect of a Halogen Atom on the 5-Endo-trig Radical Cyclization of N-Vinyl-α-halo Amides

  摘要：

  The effect of a halogen atom as a leaving group on Bu3SnH-mediated 5-endo-trig radical cyclization of N-(cyclohex-l-enyl) alpha-halo amides was examined. The cyclization of alpha-chloro amides occurred with a high degree of efficiency, whereas the corresponding alpha-iodo congeners gave only limited quantities of cyclization products. A detailed study revealed that these phenomena could be attributed to the initial conformations of alpha-halo amides. The cyclizing ability of alpha-iodo amides can be restored with Bu3SnCl or Bu3SnF as an additive. The cyclization of an alpha-iodo amide in the presence of Bu3SnF could be applied to a short-step synthesis of lycoranes featuring sequential 5-endo-trig and 6-endo-trig radical cyclizations.

  DOI：

  10.1021/jo020007u