benzyl 2-benzotriazolylpiperidine-1-carboxylate | 1027974-55-5

• 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: benzyl 2-benzotriazolylpiperidine-1-carboxylate
• 英文别名: Benzyl 2-(benzotriazol-1-yl)piperidine-1-carboxylate
• CAS: 1027974-55-5
• 化学式: C₁₉H₂₀N₄O₂
• 分子量: 336.393
• InChiKey: QXIIKZOSHWIJAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  60.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  烯丙基三甲基硅烷 、 benzyl 2-benzotriazolylpiperidine-1-carboxylate 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以93%的产率得到α-allyl-N-benzyloxycarbonylpiperidine
  参考文献：
  名称：

  Solid-Phase Synthesis of Piperidines by N-Acyliminium Ion Chemistry

  摘要：

  An efficient solid-phase procedure for the synthesis of a number of 2-substituted piperidines is reported. Starting from solid-supported carbamate-tethered delta-amino acetals, 2-benzotriazolyl-substituted (Bt-substituted) piperidines were obtained by acid-induced ring-closure followed by trapping of the transient N-acyliminium ions with benzotriazole. These 2-Bt-substituted piperidines were then used as precursors for the successful introduction of several C-nucleophiles by N-acyliminium. ion chemistry. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200209)2002:18<3133::aid-ejoc3133>3.0.co;2-h
• 作为产物：
  描述：

  5,5-diethoxy-valeronitrile 在 lithium aluminium tetrahydride 、 对甲苯磺酸 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 benzyl 2-benzotriazolylpiperidine-1-carboxylate
  参考文献：
  名称：

  Solid-Phase Synthesis of Piperidines by N-Acyliminium Ion Chemistry

  摘要：

  An efficient solid-phase procedure for the synthesis of a number of 2-substituted piperidines is reported. Starting from solid-supported carbamate-tethered delta-amino acetals, 2-benzotriazolyl-substituted (Bt-substituted) piperidines were obtained by acid-induced ring-closure followed by trapping of the transient N-acyliminium ions with benzotriazole. These 2-Bt-substituted piperidines were then used as precursors for the successful introduction of several C-nucleophiles by N-acyliminium. ion chemistry. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

  DOI：

  10.1002/1099-0690(200209)2002:18<3133::aid-ejoc3133>3.0.co;2-h

文献信息

• Solid-Phase Synthesis of Piperidines by N-Acyliminium Ion Chemistry
  作者：Johan J. N. Veerman、Jasper Klein、René W. M. Aben、Hans W. Scheeren、Chris G. Kruse、Jan H. van Maarseveen、Floris P. J. T. Rutjes、Henk Hiemstra

  DOI：10.1002/1099-0690(200209)2002:18<3133::aid-ejoc3133>3.0.co;2-h

  日期：2002.9

  An efficient solid-phase procedure for the synthesis of a number of 2-substituted piperidines is reported. Starting from solid-supported carbamate-tethered delta-amino acetals, 2-benzotriazolyl-substituted (Bt-substituted) piperidines were obtained by acid-induced ring-closure followed by trapping of the transient N-acyliminium ions with benzotriazole. These 2-Bt-substituted piperidines were then used as precursors for the successful introduction of several C-nucleophiles by N-acyliminium. ion chemistry. (C) Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.