N-(2-allyl-2-cyclohexen-1-yl)-N-(2-iodophenyl)methanesulfonamide | 167102-94-5

• 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-allyl-2-cyclohexen-1-yl)-N-(2-iodophenyl)methanesulfonamide
• 英文别名: N-(2-iodophenyl)-N-(2-prop-2-enylcyclohex-2-en-1-yl)methanesulfonamide
• CAS: 167102-94-5
• 化学式: C₁₆H₂₀INO₂S
• 分子量: 417.311
• InChiKey: CSUNHDCMKNRVMK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-allyl-2-cyclohexen-1-yl)-N-(2-iodophenyl)methanesulfonamide 在 sodium periodate 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 乙醚 、 乙醇 、 水 、 丙酮 、 叔丁醇 为溶剂， 反应 21.0h， 生成 N-(2-iodophenyl)-N-[2-(oxoethyl)cyclohex-2-enyl]methanesulfonamide
  参考文献：
  名称：

  Tandem Radical Cyclizations on Iodoaryl Azides:  Synthesis of the Core Tetracycle of Aspidosperma Alkaloids

  摘要：

  A new stereoselective approach to the tetracyclic core of Aspidosperma, alkaloids is described. Selective attack by tristrimethylsilylsilyl radicals on the aryl carbon-iodine bond of iodoaryl azides was first demonstrated on the simple model 15, thus both extending the recent discoveries of Kim and co-workers on aliphatic C-I bonds and demonstrating that the selectivity can be exploited in cascade radical cyclizations. Extension to the more complex substrate 25 afforded the core ABCE tetracyclic skeleton of the alkaloids in excellent yield and with efficient control of relative stereochemistry.

  DOI：

  10.1021/jo990891x
• 作为产物：
  描述：

  2-碘苯胺 在 吡啶 、 4-二甲氨基吡啶 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 N-(2-allyl-2-cyclohexen-1-yl)-N-(2-iodophenyl)methanesulfonamide
  参考文献：
  名称：

  Tandem Radical Cyclizations on Iodoaryl Azides:  Synthesis of the Core Tetracycle of Aspidosperma Alkaloids

  摘要：

  A new stereoselective approach to the tetracyclic core of Aspidosperma, alkaloids is described. Selective attack by tristrimethylsilylsilyl radicals on the aryl carbon-iodine bond of iodoaryl azides was first demonstrated on the simple model 15, thus both extending the recent discoveries of Kim and co-workers on aliphatic C-I bonds and demonstrating that the selectivity can be exploited in cascade radical cyclizations. Extension to the more complex substrate 25 afforded the core ABCE tetracyclic skeleton of the alkaloids in excellent yield and with efficient control of relative stereochemistry.

  DOI：

  10.1021/jo990891x

文献信息

• Replacing tin in radical chemistry: N-ethylpiperidine hypophosphite in cyclisation reactions of aryl radicals
  作者：Concepcion Gonzalez Martin、John A Murphy、Christopher R Smith

  DOI：10.1016/s0040-4039(00)00010-1

  日期：2000.3

  A detailed study of aryl radical cyclisations using N-ethylpiperidine hypophosphite shows that the reagent has advantages over tributyltin hydride in radical generation and reaction.

  使用N-乙基哌啶次磷酸对芳基进行环化的详细研究表明，该试剂在自由基的产生和反应方面比氢化三丁基锡具有优势。
• Stereoselective preparation of the ABCE tetracycle of aspidospermidine and related alkaloids
  作者：Murat Kizil、John A. Murphy

  DOI：10.1039/c39950001409

  日期：——

  Tandem radical cyclisation affords Stereoselective access to the ABCE tetracyclic substructure of aspidospermidine and related alkaloids.

  串联自由基环化技术可立体选择性地获得阿司匹南苷和相关生物碱的 ABCE 四环亚结构。