dimethyl N-nitroso-cis-2,6-piperidinedicarboxylate | 22910-15-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl N-nitroso-cis-2,6-piperidinedicarboxylate
• 英文别名: dimethyl (2R,6S)-1-nitrosopiperidine-2,6-dicarboxylate
• CAS: 22910-15-2
• 化学式: C₉H₁₄N₂O₅
• 分子量: 230.221
• InChiKey: RGVQTLZCZAVILP-KNVOCYPGSA-N

物化性质

• 沸点：
  350.1±42.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  85.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  甲醇 、 (2R,6S)-1-nitrosopiperidine-2,6-dicarboxylic acid 生成 dimethyl N-nitroso-cis-2,6-piperidinedicarboxylate
  参考文献：
  名称：

  Synthesis of a key intermediate in the diaminopimelate pathway to L-Lysine: 2,3,4,5-tetrahydrodipicolinic acid

  摘要：

  2,3,4,5-Tetrahydrodipicolinic acid (3) is a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7). It was synthesized as the stable racemic potassium salt (25) from dipicolinic acid (14) by esterification, hydrogenation to the cis-diester (17), followed by elimination of p-toluenesuifinic acid from the N-toluenesulfonyl derivative (24) of dimethyl cis-piperidine-2,6-dicarboxylate with concomitant cleavage of the ester groups. (+/-)-2,3,4,5-Tetrahydrodipicolinic acid is unstable in neutral or acidic solution, and in basic solution it exists in equilibrium with the corresponding enamine (27) and 2-oxo-6-aminoadipate (26).

  DOI：

  10.1016/0040-4020(95)00618-i

文献信息

• Synthesis of a key intermediate in the diaminopimelate pathway to L-Lysine: 2,3,4,5-tetrahydrodipicolinic acid
  作者：Ewan J.T. Chrystal、Lynda Couper、David J. Robins

  DOI：10.1016/0040-4020(95)00618-i

  日期：1995.9

  2,3,4,5-Tetrahydrodipicolinic acid (3) is a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7). It was synthesized as the stable racemic potassium salt (25) from dipicolinic acid (14) by esterification, hydrogenation to the cis-diester (17), followed by elimination of p-toluenesuifinic acid from the N-toluenesulfonyl derivative (24) of dimethyl cis-piperidine-2,6-dicarboxylate with concomitant cleavage of the ester groups. (+/-)-2,3,4,5-Tetrahydrodipicolinic acid is unstable in neutral or acidic solution, and in basic solution it exists in equilibrium with the corresponding enamine (27) and 2-oxo-6-aminoadipate (26).