N-(4-nitrophenyl)-3-(phenylselanyl)piperidine | 1167445-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N-(4-nitrophenyl)-3-(phenylselanyl)piperidine
• 英文别名: 1-(4-Nitrophenyl)-3-phenylselanylpiperidine；1-(4-nitrophenyl)-3-phenylselanylpiperidine
• CAS: 1167445-46-6
• 化学式: C₁₇H₁₈N₂O₂Se
• 分子量: 361.302
• InChiKey: KLIHEYAUBBQUPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.01
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  49.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(4-nitrophenyl)-N-(pent-4-enyl)-4-methylbenzenesulfonamide 、 苯基溴化硒 在 silver hexafluoroantimonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 N-(4-nitrophenyl)-2-((phenylselanyl)methyl)pyrrolidine 、 N-(4-nitrophenyl)-3-(phenylselanyl)piperidine
  参考文献：
  名称：

  Seleniranium Ion-Triggered Reactions: New Aspects of Friedel−Crafts and N-Detosylative Cyclizations

  摘要：

  Seleniranium ions at low temperatures (-90 to -78 degrees C) will initiate effective Friedel-Crafts cyclization if a suitably placed arene is allowed to react even when the arene is unactivated. These intermediates generated from N-aryl-N-tosylamides undergo a novel, surprisingly efficient, detosylative cyclization to form 5- or 6-membered nitrogen heterocycles. A debenzylation route is preferred if both benzyl and tosyl groups are present in the substrate.

  DOI：

  10.1021/ol900961m

文献信息

• Seleniranium Ion-Triggered Reactions: New Aspects of Friedel−Crafts and N-Detosylative Cyclizations
  作者：Hwan Jung Lim、T. V. RajanBabu

  DOI：10.1021/ol900961m

  日期：2009.7.2

  Seleniranium ions at low temperatures (-90 to -78 degrees C) will initiate effective Friedel-Crafts cyclization if a suitably placed arene is allowed to react even when the arene is unactivated. These intermediates generated from N-aryl-N-tosylamides undergo a novel, surprisingly efficient, detosylative cyclization to form 5- or 6-membered nitrogen heterocycles. A debenzylation route is preferred if both benzyl and tosyl groups are present in the substrate.