Methyl 1-(4-methylphenyl)sulfonyl-4-oxopiperidine-3-carboxylate | 1548597-52-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 1-(4-methylphenyl)sulfonyl-4-oxopiperidine-3-carboxylate
• CAS: 1548597-52-9
• 化学式: C₁₄H₁₇NO₅S
• 分子量: 311.359
• InChiKey: XUEBXCQTTOILCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  89.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 1-(4-methylphenyl)sulfonyl-4-oxopiperidine-3-carboxylate 在 potassium carbonate 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 N-(4-hydroxy-6-tosyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)-2-propylpentanamide
  参考文献：
  名称：

  Discovery of tetrahydropyrido[4,3-d]pyrimidine derivatives for the treatment of neuropathic pain

  摘要：

  A series of tetrahydropyridopyrimidine derivatives were synthesized and evaluated for neurotoxicity and peripheral analgesic activity followed by assessment of antiallodynic and antihyperalgesic potential in two peripheral neuropathic pain models, the chronic constriction injury (CCI) and partial sciatic nerve ligation (PSNL). Compounds (4b and 4d) exhibiting promising efficacies in four behavioral assays of allodynia and hyperalgesia (spontaneous pain, tactile allodynia, cold allodynia and mechanical hyperalgesia) were quantified for their ED50 values (15.12-65.10 mg/kg). Studies carried out to assess the underlying mechanism revealed that the compounds suppressed the inflammatory component of the neuropathic pain and prevented oxidative and nitrosative stress. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.007
• 作为产物：
  描述：

  4-哌啶酮 在 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 Methyl 1-(4-methylphenyl)sulfonyl-4-oxopiperidine-3-carboxylate
  参考文献：
  名称：

  Discovery of tetrahydropyrido[4,3-d]pyrimidine derivatives for the treatment of neuropathic pain

  摘要：

  A series of tetrahydropyridopyrimidine derivatives were synthesized and evaluated for neurotoxicity and peripheral analgesic activity followed by assessment of antiallodynic and antihyperalgesic potential in two peripheral neuropathic pain models, the chronic constriction injury (CCI) and partial sciatic nerve ligation (PSNL). Compounds (4b and 4d) exhibiting promising efficacies in four behavioral assays of allodynia and hyperalgesia (spontaneous pain, tactile allodynia, cold allodynia and mechanical hyperalgesia) were quantified for their ED50 values (15.12-65.10 mg/kg). Studies carried out to assess the underlying mechanism revealed that the compounds suppressed the inflammatory component of the neuropathic pain and prevented oxidative and nitrosative stress. (C) 2013 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bioorg.2013.11.007

文献信息

• Efficient Synthesis of 3<i>H</i>-Indoles Enabled by the Lead-Mediated α-Arylation of β-Ketoesters or γ-Lactams Using Aryl Azides
  作者：Fei Zhou、Tom G. Driver

  DOI：10.1021/ol5010615

  日期：2014.6.6

  of a lead-mediated α-arylation reaction between aryl azides and β-ketoesters or γ-lactams that facilitates the formation of 3H-indoles is disclosed. Twenty-five examples are included which demonstrate the generality of this reaction to access aryl azides bearing tetrasubstituted o-alkyl substituents. When paired with a Staudinger reduction, this reaction streamlines the synthesis of functionalized 3H-indoles

  公开了在芳基叠氮化物和β-酮酯或γ-内酰胺之间促进3 H-吲哚形成的铅介导的α-芳基化反应的发展。包括的二十五个例子证明了该反应的普遍性，以获得带有四取代的邻烷基取代基的芳基叠氮化物。当与施陶丁格还原配对时，该反应简化了功能化 3 H-吲哚的合成。
• Effect of a <i>cis</i>-4-aminopiperidine-3-carboxylic acid (<i>cis</i>-APiC) residue on mixed-helical folding of unnatural peptides
  作者：Sunglim Choi、Jihyun Shim、Philjae Kang、Soo Hyuk Choi

  DOI：10.1039/d1ob02223g

  日期：——

  solubility in aqueous solution. In this regard, we chose cis-4-aminopiperidine-3-carboxylic acid (cis-APiC) as a foldamer building block that can provide both sufficient aqueous solubility and mixed-helical propensity. Conformational analyses of α/β- and β-peptides containing a cis-APiC residue by circular dichroism spectroscopy and single-crystal X-ray crystallography suggest that the incorporation of cis-APiC

  α/β-肽11/9-螺旋和β-肽12/10-螺旋属于“混合”螺旋，其中两种方向相反的氢键沿螺旋轴交替。与其他无环 β-残基相比，顺式-2-氨基环己烷羧酸 ( cis -ACHC) 已知能促进这些混合螺旋并更稳定螺旋倾向。混合螺旋骨架的应用仍然需要在水溶液中具有足够的溶解度。在这方面，我们选择了顺式-4-氨基哌啶-3-羧酸（顺式-APiC）作为折叠体结构单元，它可以提供足够的水溶性和混合螺旋倾向。含有顺式的α/β-和β-肽的构象分析圆二色光谱和单晶X射线晶体学的-APiC残基表明，顺式-APiC而不是顺式-ACHC的掺入可以增强混合螺旋肽的水溶性，而对螺旋折叠没有任何不利影响。此外，β-肽的右手和左手 12/10-螺旋之间的比率可以通过cis -APiC 残基的局部构象之间的相对能量来合理化。