Tert-butyl 3-[2-(4-nitrophenyl)ethyl]-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate | 1017803-44-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: Tert-butyl 3-[2-(4-nitrophenyl)ethyl]-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate
• CAS: 1017803-44-9
• 化学式: C₂₆H₃₂N₄O₅
• 分子量: 480.564
• InChiKey: DJGZOMATSMMMTN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  98.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-硝基苯乙基溴 、 tert-butyl 4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate 在 sodium hydride 作用下， 以 甲苯 为溶剂， 以8%的产率得到Tert-butyl 3-[2-(4-nitrophenyl)ethyl]-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate
  参考文献：
  名称：

  Practical Synthesis ofp‐Aminophenethylspiperone (NAPS), a High‐Affinity, Selective D₂‐Dopamine Receptor Antagonist

  摘要：

  Because attempts to scale up the published synthetic preparation of p-aminophenethylspiperone (NAPS) by N-alkylation of spiperone with 4-nitrophenethyl bromide followed by reduction gave poor yields and difficulties during purification, an alternative synthetic approach has been developed. Use of 4-(N-tert-butyloxycarbonyl) aminophenethyl bromide to alkylate spiperone followed by the Boc group deprotection gave NAPS in 56% yield. This procedure provides an improved and efficient synthesis of the important high-affinity, selective D-2-dopamine receptor antagonist NAPS.

  DOI：

  10.1080/00397910701821135

文献信息

• Practical Synthesis of<i>p</i>‐Aminophenethylspiperone (NAPS), a High‐Affinity, Selective D₂‐Dopamine Receptor Antagonist
  作者：Chunyang Jin、Louise D. Mayer、Anita H. Lewin、Kenneth S. Rehder、George A. Brine

  DOI：10.1080/00397910701821135

  日期：2008.2.13

  Because attempts to scale up the published synthetic preparation of p-aminophenethylspiperone (NAPS) by N-alkylation of spiperone with 4-nitrophenethyl bromide followed by reduction gave poor yields and difficulties during purification, an alternative synthetic approach has been developed. Use of 4-(N-tert-butyloxycarbonyl) aminophenethyl bromide to alkylate spiperone followed by the Boc group deprotection gave NAPS in 56% yield. This procedure provides an improved and efficient synthesis of the important high-affinity, selective D-2-dopamine receptor antagonist NAPS.