(2SR,5SR)-1-tert-butyl 2-methyl 5-(methylsulfonyloxy)piperidine-1,2-dicarboxylate

• 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: (2SR,5SR)-1-tert-butyl 2-methyl 5-(methylsulfonyloxy)piperidine-1,2-dicarboxylate
• 英文别名: 1-tert-Butyl 2-methyl (2S,5S)-5-[(methylsulfonyl)oxy]piperidine-1,2-dicarboxylate；1-O-tert-butyl 2-O-methyl (2S,5S)-5-methylsulfonyloxypiperidine-1,2-dicarboxylate
• 化学式: C₁₃H₂₃NO₇S
• 分子量: 337.394
• InChiKey: RVYCMNKPCZDJEQ-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2SR,5SR)-1-tert-butyl 2-methyl 5-(methylsulfonyloxy)piperidine-1,2-dicarboxylate 在 palladium on activated charcoal sodium azide 、 氢气 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 65.0 ℃ 、101.33 kPa 条件下， 生成 (2SR,5RS)-tert-butyl 2-methyl trans-5-aminopiperidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of 5-substituted pipecolic acid derivatives as new conformationally constrained ornithine and arginine analogues

  摘要：

  Two, orthogonally protected, constrained analogues of arginine have been synthesised in a diastereodivergent manner. The key step involved an electrophilic or radical functionalisation of methyl N-Boc-5,6-dehydropipecolate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.008
• 作为产物：
  描述：

  1-叔丁基2-甲基5-氧杂哌啶-1,2-二羧酸 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 (2SR,5SR)-1-tert-butyl 2-methyl 5-(methylsulfonyloxy)piperidine-1,2-dicarboxylate
  参考文献：
  名称：

  Synthesis of 5-substituted pipecolic acid derivatives as new conformationally constrained ornithine and arginine analogues

  摘要：

  Two, orthogonally protected, constrained analogues of arginine have been synthesised in a diastereodivergent manner. The key step involved an electrophilic or radical functionalisation of methyl N-Boc-5,6-dehydropipecolate. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.008

文献信息

• Diastereoselective functionalizations of enecarbamates derived from pipecolic acid towards 5-guanidinopipecolates as arginine mimetics
  作者：Laurent Le Corre、Jean-Claude Kizirian、Camille Levraud、Jean-Luc Boucher、Véronique Bonnet、Hamid Dhimane

  DOI：10.1039/b805811c

  日期：——

  Various substituents could be diastereoselectively introduced into the 5-position of pipecolic acid via electrophilic or free-radical-initiated addition to the carbon–carbon double bond of endocyclic enecarbamates derived from pipecolic acid. This study allowed the diastereoselective synthesis of both cis- and trans-5-guanidino pipecolates, which were designed as constrained arginine mimetics and whose potential inhibition of nitric oxide synthase (NOS) was evaluated with three NOS isoforms.

  各种取代基可以通过电亲核反应或自由基引发的方式，选择性地引入到哌啶酸的5位。这是通过对来源于哌啶酸的内环烯酰胺的碳碳双键进行加成反应实现的。该研究实现了顺式和反式5-氨基脯氨酸的选择性合成，这些化合物被设计为受限的精氨酸类似物，并且对三种一氧化氮合酶（NOS）异构体的潜在抑制作用进行了评估。
• Aminopiperidine Quinolines and Their Azaisosteric Analogues with Antibacterial Activity
  申请人：Reck Folkert

  公开号：US20090131444A1

  公开（公告）日：2009-05-21

  The present invention relates to compounds that demonstrate antibacterial activity, processes for their preparation, pharmaceutical compositions containing them as the active ingredient, to their use as medicaments and to their use in the manufacture of medicaments for use in the treatment of bacterial infections in warm blooded animals such as humans. In particular this invention relates to compounds useful for the treatment of bacterial infections in warm-blooded animals such as humans, more particularly to the use of these compounds in the manufacture of medicaments for use in the treatment of bacterial infections in warm blooded animals such as humans.

  本发明涉及表现出抗菌活性的化合物、其制备过程、包含它们作为活性成分的药物组合物、它们作为药物的使用以及它们在制造用于治疗温血动物（如人类）的细菌感染的药物方面的使用。特别地，本发明涉及用于治疗温血动物（如人类）细菌感染的有用化合物，更具体地涉及使用这些化合物制造用于治疗温血动物（如人类）细菌感染的药物。
• WO2006/125974
  申请人：——

  公开号：——

  公开（公告）日：——
• Synthesis of 5-substituted pipecolic acid derivatives as new conformationally constrained ornithine and arginine analogues
  作者：Laurent Le Corre、Hamid Dhimane

  DOI：10.1016/j.tetlet.2005.09.008

  日期：2005.10

  Two, orthogonally protected, constrained analogues of arginine have been synthesised in a diastereodivergent manner. The key step involved an electrophilic or radical functionalisation of methyl N-Boc-5,6-dehydropipecolate. (c) 2005 Elsevier Ltd. All rights reserved.