1-amino-2(S)-(benzylamino)pentane | 150482-71-6

• 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: 1-amino-2(S)-(benzylamino)pentane
• 英文别名: (2S)-2-N-benzylpentane-1,2-diamine
• CAS: 150482-71-6
• 化学式: C₁₂H₂₀N₂
• 分子量: 192.304
• InChiKey: RFJIMTUIPSHUSL-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-amino-2(S)-(benzylamino)pentane 在 palladium on barium sulfate 氢气 、 三乙胺 作用下， 以 甲醇 、 乙醇 为溶剂， 25.0 ℃ 、310.27 kPa 条件下， 反应 25.5h， 生成 6-<(2(S)-aminopentyl)amino>-2,5-diamino-4(3H)-pyrimidinone
  参考文献：
  名称：

  Synthesis of tetrahydropteridine C6-stereoisomers, including N5-formyl-(6S)-tetrahydrofolic acid

  摘要：

  Chiral N1-protected vicinal diamines derived from amino acids were condensed with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone, the nitro group reduced, and the amine deprotected. oxidative cyclization of the resulting triaminopyrimidinone via quinoid pyrimidine intermediates gave a quinoid dihydropteridine, which was then reduced to a tetrahydropteridine C6-stereoisomer. Thus, 6(R)- and 6(S)-propyltetrahydropterin were stereospecifically synthesized (99% enantiomeric purity) in good yield from D- and L-norvaline, respectively. Reductive alkylation of (p-aminobenzoyl)-L-glutamate with a nitropyrimidine aldehyde derived from D- or L-serine similarly afforded, after cyclization and reduction, (6R)- or (6S)-tetrahydrofolic acid. The latter was then converted to the natural isomer of leucovorin by regioselective N5-formylation with carbonyl diimidazole/formic acid without loss of enantiomeric purity.

  DOI：

  10.1021/jo00042a030
• 作为产物：
  描述：

  N-benzylidene-L-norvalinamide 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 生成 1-amino-2(S)-(benzylamino)pentane
  参考文献：
  名称：

  Synthesis of tetrahydropteridine C6-stereoisomers, including N5-formyl-(6S)-tetrahydrofolic acid

  摘要：

  Chiral N1-protected vicinal diamines derived from amino acids were condensed with 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone, the nitro group reduced, and the amine deprotected. oxidative cyclization of the resulting triaminopyrimidinone via quinoid pyrimidine intermediates gave a quinoid dihydropteridine, which was then reduced to a tetrahydropteridine C6-stereoisomer. Thus, 6(R)- and 6(S)-propyltetrahydropterin were stereospecifically synthesized (99% enantiomeric purity) in good yield from D- and L-norvaline, respectively. Reductive alkylation of (p-aminobenzoyl)-L-glutamate with a nitropyrimidine aldehyde derived from D- or L-serine similarly afforded, after cyclization and reduction, (6R)- or (6S)-tetrahydrofolic acid. The latter was then converted to the natural isomer of leucovorin by regioselective N5-formylation with carbonyl diimidazole/formic acid without loss of enantiomeric purity.

  DOI：

  10.1021/jo00042a030