4-aminomethyl-N¹-[(2-trimethylsilyl)ethoxycarbonyl]piperidine | 769954-33-8

• 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: 4-aminomethyl-N¹-[(2-trimethylsilyl)ethoxycarbonyl]piperidine
• 英文别名: 4-aminomethyl-N-[2-(trimethylsilyl)ethoxycarbonyl]piperidine；2-Trimethylsilylethyl 4-(aminomethyl)piperidine-1-carboxylate
• CAS: 769954-33-8
• 化学式: C₁₂H₂₆N₂O₂Si
• 分子量: 258.436
• InChiKey: WHJVZCHMRTWRNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-aminomethyl-N¹-[(2-trimethylsilyl)ethoxycarbonyl]piperidine 、 (S)-N-(p-nitrobenzenesulfonyl)-2-benzylaziridine 生成 N-{(1S)-2-[4-(aminomethyl)piperidin-1-yl]-1-benzylethyl}-4-nitrobenzenesulfonamide
  参考文献：
  名称：

  微波结合树脂结合的胺类化合物对活化氮丙啶的开环

  摘要：

  本文描述了在固相合成（SPS）中在微波辐射条件下，由Nosylamide活化的氮丙啶进行亲核开环的第一个研究。研究了溶剂，温度，反应时间和试剂比率对部分保护的三胺与氮丙啶和树脂结合的二胺的SPS的影响。还对该方法进行了优化，以合成新的氨基酸衍生物。

  DOI：

  10.1021/jo702612u
• 作为产物：
  描述：

  对硝基苯基三甲基硅乙基碳酸酯 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 26.0h， 生成 4-aminomethyl-N¹-[(2-trimethylsilyl)ethoxycarbonyl]piperidine
  参考文献：
  名称：

  Solid-Phase Synthesis of Rigid Acylpolyamines Using Temporary N-4,4‘-Dimethoxytrityl Protection in the Presence of Trityl Linkers

  摘要：

  An N-protection protocol employing the 4,4'-dimethoxytrityl (Dmt) group in combination with borane reduction of resin-bound polyamides was shown to be an efficient methodology that enables synthesis of novel analogues of natural acylpolyamine toxins. Thus, three philanthotoxins containing polyamine chains with piperidyl and cyclohexyl structural elements, which introduce conformational rigidity, increased lipophilicity, and altered proteolytic properties, were obtained in 39-44% overall yield.

  DOI：

  10.1021/jo049278q

文献信息

• Solid-Phase Synthesis of Rigid Acylpolyamines Using Temporary <i>N</i>-4,4‘-Dimethoxytrityl Protection in the Presence of Trityl Linkers
  作者：Christian A. Olsen、Matthias Witt、Jerzy W. Jaroszewski、Henrik Franzyk

  DOI：10.1021/jo049278q

  日期：2004.9.1

  An N-protection protocol employing the 4,4'-dimethoxytrityl (Dmt) group in combination with borane reduction of resin-bound polyamides was shown to be an efficient methodology that enables synthesis of novel analogues of natural acylpolyamine toxins. Thus, three philanthotoxins containing polyamine chains with piperidyl and cyclohexyl structural elements, which introduce conformational rigidity, increased lipophilicity, and altered proteolytic properties, were obtained in 39-44% overall yield.
• Microwave-Assisted Ring-Opening of Activated Aziridines with Resin-Bound Amines
  作者：François Crestey、Matthias Witt、Karla Frydenvang、Dan Stærk、Jerzy W. Jaroszewski、Henrik Franzyk

  DOI：10.1021/jo702612u

  日期：2008.5.1

  nosylamide-activated aziridines under microwave irradiation conditions in solid-phase synthesis (SPS). The effects of solvent, temperature, reaction time, and reagent ratio in SPS of partially protected triamines from aziridines and resin-bound diamines were investigated. The methodology was also optimized for the synthesis of novel amino acid derivatives.

  本文描述了在固相合成（SPS）中在微波辐射条件下，由Nosylamide活化的氮丙啶进行亲核开环的第一个研究。研究了溶剂，温度，反应时间和试剂比率对部分保护的三胺与氮丙啶和树脂结合的二胺的SPS的影响。还对该方法进行了优化，以合成新的氨基酸衍生物。