cis-2,6-piperidinedicarboxamide | 99669-83-7

• 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: cis-2,6-piperidinedicarboxamide
• 英文别名: meso-piperidine-2,6-dicarboxamide；cis-piperidine-2,6-dicarboxamide；cis-Piperidin-2,6-dicarbamid；(2S,6R)-piperidine-2,6-dicarboxamide
• CAS: 99669-83-7
• 化学式: C₇H₁₃N₃O₂
• 分子量: 171.199
• InChiKey: LOVQGUOGVLKMQT-SYDPRGILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  98.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  cis-2,6-piperidinedicarboxamide 在 barium dihydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 以79%的产率得到cis-2,6-piperidinedicarboxylic acid
  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：

  2,6-二溴庚二酸二乙酯 在 氨 作用下， 反应 72.0h， 以20%的产率得到trans-2,6-piperidinedicarboxamide
  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

• Practical biocatalytic desymmetrization of meso-N-heterocyclic dicarboxamides and their application in the construction of aza-sugar containing nucleoside analogs
  作者：Peng Chen、Ming Gao、De-Xian Wang、Liang Zhao、Mei-Xiang Wang

  DOI：10.1039/c2cc18012j

  日期：——

  Amidase-catalyzed desymmetrization of meso-N-heterocyclic dicarboxamides under very mild conditions provided a highly efficient and practical method for the preparation of enantiomerically pure carbamoyl-substituted heterocyclic amino acids that were unique and versatile platforms for the construction of both antipodes of aza-sugar containing nucleoside analogs.

  在非常温和的条件下，酰胺酶催化的内消旋-N-杂环二甲酰胺的脱对称化为制备对映体纯的氨基甲酰基取代的杂环氨基酸提供了一种高效实用的方法，这是构建氮杂糖两个对映体的独特且通用的平台含有核苷类似物。
• 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).