dimethyl N-toluenesulfonyl-cis-2,6-piperidinedicarboxylate | 142055-40-1

• 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-toluenesulfonyl-cis-2,6-piperidinedicarboxylate
• CAS: 142055-40-1
• 化学式: C₁₆H₂₁NO₆S
• 分子量: 355.412
• InChiKey: VDBQQBVKAWILFN-OKILXGFUSA-N

物化性质

• 沸点：
  467.2±55.0 °C(Predicted)
• 密度：
  1.286±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.25
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  89.98
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl N-toluenesulfonyl-cis-2,6-piperidinedicarboxylate 在 potassium tert-butylate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以41%的产率得到potassium salt of (+/-)-2,3,4,5-tetrahydrodipicolinate
  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
• 作为产物：
  描述：

  dimethyl (2R,6S)-piperidine-2,6-dicarboxylate 生成 dimethyl N-toluenesulfonyl-cis-2,6-piperidinedicarboxylate
  参考文献：
  名称：

  Synthesis of the potassium salt of 2,3,4,5-tetrahydrodipicolinic acid, a key intermediate in the diaminopimelate pathway to L-lysine

  摘要：

  The potassium salt (13) of 2,3,4,5-tetrahydrodipicolinic acid, a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7), has been prepared by elimination of p-toluenesulphinic acid from the N-toluenesulphonyl derivative (12) of dimethyl cis-piperidine-2,6-dicarboxylate with simultaneous cleavage of the ester groups. 2,3,4,5-Tetrahydrodipicolinic acid exists in solution in equilibrium with the corresponding enamine (15) and an open chain form (14), and serves as a substrate for meso-DAP dehydrogenase on the biosynthetic pathway to L-lysine (7).

  DOI：

  10.1016/s0040-4039(00)79065-4

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

  DOI：10.1016/s0040-4039(00)79065-4

  日期：1992.5

  The potassium salt (13) of 2,3,4,5-tetrahydrodipicolinic acid, a key intermediate in the diaminopimelate (DAP) pathway to L-lysine (7), has been prepared by elimination of p-toluenesulphinic acid from the N-toluenesulphonyl derivative (12) of dimethyl cis-piperidine-2,6-dicarboxylate with simultaneous cleavage of the ester groups. 2,3,4,5-Tetrahydrodipicolinic acid exists in solution in equilibrium with the corresponding enamine (15) and an open chain form (14), and serves as a substrate for meso-DAP dehydrogenase on the biosynthetic pathway to L-lysine (7).