(2R)-2-哌嗪羧酰胺 | 138681-31-9

• 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
• 中文名称: (2R)-2-哌嗪羧酰胺
• 英文名称: R-(+)-Piperazine-2-carboxamide
• 英文别名: (R)-piperazine-2-carboxamide；(2R)-piperazine-2-carboxamide
• CAS: 138681-31-9
• 化学式: C₅H₁₁N₃O
• 分子量: 129.162
• InChiKey: BRYCUMKDWMEGMK-SCSAIBSYSA-N

物化性质

• 沸点：
  364.2±37.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  67.2
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-2-哌嗪羧酰胺 在 盐酸 作用下， 反应 4.0h， 生成 (R)-哌嗪-2-羧酸
  参考文献：
  名称：

  Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells

  摘要：

  Whole bacterial cells containing stereospecific amidases were used for the kinetic resolution of racemic piperazine-2-carboxamide and piperidine-2-carboxamide to (S)- and (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid, respectively. (S)-Piperazinecarboxylic acid dihydrochloride produced with the biocatalysts Klebsiella terrigena DSM 9174 had an ee value of 99.4% (41% yield), and the ee value of (R)-piperazinecarboxylic acid dihydrochloride obtained with Burkholderia sp. DSM 9925 was 99.0% (22% yield). Using Pseudomonas fluorescens DSM 9924 (S)-piperidine-2-carboxylic acid with an ee value of 97.3% (20% yield) was isolated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00256-5
• 作为产物：
  描述：

  吡嗪酰胺 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 85.0 ℃ 、2.0 MPa 条件下， 反应 5.0h， 生成 (2R)-2-哌嗪羧酰胺
  参考文献：
  名称：

  Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells

  摘要：

  Whole bacterial cells containing stereospecific amidases were used for the kinetic resolution of racemic piperazine-2-carboxamide and piperidine-2-carboxamide to (S)- and (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid, respectively. (S)-Piperazinecarboxylic acid dihydrochloride produced with the biocatalysts Klebsiella terrigena DSM 9174 had an ee value of 99.4% (41% yield), and the ee value of (R)-piperazinecarboxylic acid dihydrochloride obtained with Burkholderia sp. DSM 9925 was 99.0% (22% yield). Using Pseudomonas fluorescens DSM 9924 (S)-piperidine-2-carboxylic acid with an ee value of 97.3% (20% yield) was isolated. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00256-5

文献信息

• Adenosine re-uptake inhibiting derivatives of diphenyl oxazoles,
  申请人：Bristol-Myers Squibb Company

  公开号：US05382584A1

  公开（公告）日：1995-01-17

  A series of 1-piperazinyl-N-phenylacetamide derivatives of 4,5-diphenyl-oxazoles, thiazoles, and imidazoles which are novel adenosine transport inhibitors have been found to provide effective antiischemic protection for CNS and cardiac tissue, particularly neurons. A method of treatment to protect against CNS ischemia, such as that resulting from trauma, stroke, or other ischemic conditions, comprises administration of these novel compounds to an individual in need of such treatment.

  一系列1-哌嗪基-N-苯乙酰胺衍生物的4,5-二苯基噁唑，噻唑和咪唑被发现是新型的腺苷转运抑制剂，可为中枢神经系统和心脏组织，尤其是神经元提供有效的抗缺血保护。一种治疗方法，用于保护中枢神经系统缺血，例如由创伤，中风或其他缺血病症引起，包括向需要此类治疗的个体投药这些新型化合物。
• Biocatalyst Immobilization and Process Intensification: Production of (<i>S</i>)-Piperazine-2-carboxylic Acid Dihydrochloride
  作者：David Roura Padrosa、Dennis Wetzl、Stefan Hildbrand、Paolo Tosatti、Joerg Sedelmeier、Kurt Puentener、Hans Iding、Francesca Paradisi

  DOI：10.1021/acs.oprd.3c00347

  日期：——

  (LAP2) for the chiral resolution of racemic piperazine-2-carboxamide into enantiopure (S)-piperazine-2-carboxylic acid. After characterizing the free enzyme, we also achieved its first immobilization at high loadings (>20 mgprotein/gsupport) by testing different commercially available methacrylic resins. The immobilized catalyst showed 48–67% of retained activity and could be reused for more than 10 cycles

  生物催化，即利用酶来生产化学品，与传统有机化学相比具有许多优势。最重要的是可以实现的优异的区域选择性、化学选择性和立体选择性、高官能团耐受性以及生物催化转化通常可以在纯水中进行这一事实。在这项工作中，我们应用来自米曲霉(LAP2) 的半纯化氨肽酶将外消旋哌嗪-2-甲酰胺手性拆分成对映体纯 ( S )-哌嗪-2-羧酸。在表征游离酶后，我们还通过测试不同的市售甲基丙烯酸树脂实现了其在高负载量（> 20 mg蛋白质/g支持物）下的首次固定。固定化催化剂显示出 48-67% 的保留活性，并且可以批量重复使用 10 次以上，而没有任何明显的活性损失。此外，我们还将固定化酶集成到连续流动模式中，这使得生产率显着提高，并允许连续运行超过24小时而不影响反应产率。
• Preparation of (S)-piperazine-2-carboxylic acid, (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid by kinetic resolution of the corresponding racemic carboxamides with stereoselective amidases in whole bacterial cells
  作者：Eric Eichhorn、Jean-Paul Roduit、Nicholas Shaw、Klaus Heinzmann、Andreas Kiener

  DOI：10.1016/s0957-4166(97)00256-5

  日期：1997.8

  Whole bacterial cells containing stereospecific amidases were used for the kinetic resolution of racemic piperazine-2-carboxamide and piperidine-2-carboxamide to (S)- and (R)-piperazine-2-carboxylic acid, and (S)-piperidine-2-carboxylic acid, respectively. (S)-Piperazinecarboxylic acid dihydrochloride produced with the biocatalysts Klebsiella terrigena DSM 9174 had an ee value of 99.4% (41% yield), and the ee value of (R)-piperazinecarboxylic acid dihydrochloride obtained with Burkholderia sp. DSM 9925 was 99.0% (22% yield). Using Pseudomonas fluorescens DSM 9924 (S)-piperidine-2-carboxylic acid with an ee value of 97.3% (20% yield) was isolated. (C) 1997 Elsevier Science Ltd.