1--5-hydroxy-5-pentane

• 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: 1--5-hydroxy-5-pentane
• 英文别名: tert-butyl (3E)-3-[5-hydroxy-5-[1-[(2-methylpropan-2-yl)oxycarbonyl]-2-oxopiperidin-3-yl]pentylidene]-2-oxopiperidine-1-carboxylate
• 化学式: C₂₅H₄₀N₂O₇
• 分子量: 480.602
• InChiKey: VMSXRGZEYCWYKB-GZTJUZNOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  34
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1--5-hydroxy-5-pentane 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以60%的产率得到tert-butyl 2-hydroxy-3-[(E)-1-hydroxy-6-(hydroxymethyl)-9-[(2-methylpropan-2-yl)oxycarbonylamino]non-5-enyl]piperidine-1-carboxylate
  参考文献：
  名称：

  Biomimetic Synthesis of Nitraramine

  摘要：

  The synthesis of a possible biosynthetic precursor (9) of nitraramine (1) is described, utilizing N-Boc-piperidone as an equivalent of didehydropiperidine 4. Heating this reactive, achiral intermediate 9 in aqueous solution results in the stereoselective formation of natural nitraramine via three successive cyclization reactions. Since nitraramine and several other Nitraria alkaloids are obtained from Nitraria species in racemic form, this synthesis provides additional support for our hypothesis of non-enzyme-catalyzed formation of these alkaloids.

  DOI：

  10.1021/jo00122a052
• 作为产物：
  描述：

  1-Boc-2-哌啶酮 在 4-甲基苯磺酸吡啶 、 三乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 丙酮 、 甲苯 为溶剂， 反应 107.0h， 生成 1--5-hydroxy-5-pentane
  参考文献：
  名称：

  Biomimetic Synthesis of Nitraramine

  摘要：

  The synthesis of a possible biosynthetic precursor (9) of nitraramine (1) is described, utilizing N-Boc-piperidone as an equivalent of didehydropiperidine 4. Heating this reactive, achiral intermediate 9 in aqueous solution results in the stereoselective formation of natural nitraramine via three successive cyclization reactions. Since nitraramine and several other Nitraria alkaloids are obtained from Nitraria species in racemic form, this synthesis provides additional support for our hypothesis of non-enzyme-catalyzed formation of these alkaloids.

  DOI：

  10.1021/jo00122a052

文献信息

• Biomimetic Synthesis of Nitraramine
  作者：Martin J. Wanner、Gerrit-Jan Koomen

  DOI：10.1021/jo00122a052

  日期：1995.9

  The synthesis of a possible biosynthetic precursor (9) of nitraramine (1) is described, utilizing N-Boc-piperidone as an equivalent of didehydropiperidine 4. Heating this reactive, achiral intermediate 9 in aqueous solution results in the stereoselective formation of natural nitraramine via three successive cyclization reactions. Since nitraramine and several other Nitraria alkaloids are obtained from Nitraria species in racemic form, this synthesis provides additional support for our hypothesis of non-enzyme-catalyzed formation of these alkaloids.