(5S)-7-methyl-1,7-diaza-spiro[4.6]undecane | 862410-80-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂螺环衍生物
• 英文名称: (5S)-7-methyl-1,7-diaza-spiro[4.6]undecane
• 英文别名: (5S)-10-methyl-1,10-diazaspiro[4.6]undecane
• CAS: 862410-80-8
• 化学式: C₁₀H₂₀N₂
• 分子量: 168.282
• InChiKey: HIWLSQFCZLBBHJ-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 (5S)-7-methyl-1,7-diaza-spiro[4.6]undecane 在 甲酸 作用下， 反应 24.0h， 以76%的产率得到(5S)-1,7-dimethyl-1,7-diaza-spiro[4.6]undecane
  参考文献：
  名称：

  Synthesis of enantiopure 5.7-spirodiamines: (S)-1,7-diaza[4.6]undecane and related compounds

  摘要：

  The efficient synthesis of enantiomerically pure (S)-1,7-diaza[4.6]undecane and (S)-7-methyl-1,7-diaza[4.6]undecane and related compounds is reported. These novel diamines are obtained from (S)-proline, which is reacted with chloral to give an enantiomerically pure oxazolidinone, which is alkylated at the alpha-position using cis-1,4-clibromobutene. The resulting allylbromide is then reacted with ammonia or methylamine to yield, as intermediates, allylamines, which ring close to give the corresponding spirolactams. The parent and the 7-methyl (S)-5.7-spirodiamines are obtained via reduction in two steps of the spirolactams. The expected absolute configuration was confirmed by X-ray structural analysis. Enantiomeric excess (> 99.8% ee) was determined using the Mosher amides of the spirodiamines and gas chromatography. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.030
• 作为产物：
  描述：

  (2R,5R)-5-(4-bromo-2-butenyl)-2-trichloromethyl-1-aza-3-oxabicyclo[3.3.0]octan-4-one 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 20.0 ℃ 、405.3 kPa 条件下， 反应 26.0h， 生成 (5S)-7-methyl-1,7-diaza-spiro[4.6]undecane
  参考文献：
  名称：

  Synthesis of enantiopure 5.7-spirodiamines: (S)-1,7-diaza[4.6]undecane and related compounds

  摘要：

  The efficient synthesis of enantiomerically pure (S)-1,7-diaza[4.6]undecane and (S)-7-methyl-1,7-diaza[4.6]undecane and related compounds is reported. These novel diamines are obtained from (S)-proline, which is reacted with chloral to give an enantiomerically pure oxazolidinone, which is alkylated at the alpha-position using cis-1,4-clibromobutene. The resulting allylbromide is then reacted with ammonia or methylamine to yield, as intermediates, allylamines, which ring close to give the corresponding spirolactams. The parent and the 7-methyl (S)-5.7-spirodiamines are obtained via reduction in two steps of the spirolactams. The expected absolute configuration was confirmed by X-ray structural analysis. Enantiomeric excess (> 99.8% ee) was determined using the Mosher amides of the spirodiamines and gas chromatography. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.04.030