(2S)-2-methyl-4,6-dioxopiperidine | 653589-26-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S)-2-methyl-4,6-dioxopiperidine
• 英文别名: (S)-6-methylpiperidine-2,4-dione；(6S)-6-methylpiperidine-2,4-dione
• CAS: 653589-26-5
• 化学式: C₆H₉NO₂
• 分子量: 127.143
• InChiKey: ANAIVIDMOFUACM-BYPYZUCNSA-N

物化性质

• 沸点：
  337.9±35.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (2S)-2-methyl-4,6-dioxopiperidine 在 potassium hydrogencarbonate 作用下， 以 四氯化碳 、 二氯甲烷 、 氯仿 为溶剂， 反应 29.0h， 生成 (S)-4-methoxy-6-methyl-1-(1-((S)-2-methyl-1-(1-((S)-2-methyl-6-oxo-1,2,3,6-tetrahydropyridin-4-yl)piperidin-4-yl)-6-oxo-1,2,3,6-tetrahydropyridin-4-yl)piperidin-4-yl)-5,6-dihydropyridin-2(1H)-one
  参考文献：
  名称：

  基于哌啶-哌啶酮的多方面二级结构模拟物

  摘要：

  极简二级结构模拟物通常被制成类似于蛋白质-蛋白质相互作用 (PPI) 中的一个界面，从而扰乱它。我们最近提出合适的化学型可以直接与界面区域匹配，而无需考虑二级结构。在这里，我们描述了新化学型1的模块化合成，其溶液态构象集合的模拟，以及与理想二级结构和 PPI 中真实界面区域的相关性。脚手架1呈现彼此完全分离的氨基酸侧链，其方向与理想的片状或螺旋结构非常相似，在 PPI 界面具有相似的非理想结构，以及其他 PPI 界面的模拟构象与任何二级结构不相似的区域. 68 种不同的 PPI，其中1 个匹配孔的构象被识别。还提出了一种新方法来确定极简模拟晶体结构与其溶液构象的相关性。因此，dld - 1 faf以比最小能量溶液状态高0.91 kcal mol -1的构象结晶。

  DOI：

  10.1002/anie.201400927
• 作为产物：
  描述：

  Boc-L-beta-高丙氨酸 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S)-2-methyl-4,6-dioxopiperidine
  参考文献：
  名称：

  Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor

  摘要：

  tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-(OBu)-Bu-t and other beta-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy delta-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo-1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).

  DOI：

  10.1021/jo0353886

文献信息

• Protein–Protein Interface Mimicry by an Oxazoline Piperidine-2,4-dione
  作者：Xun Li、Jaru Taechalertpaisarn、Dongyue Xin、Kevin Burgess

  DOI：10.1021/ol5036547

  日期：2015.2.6

  Representative minimalist mimics 1 were prepared from amino acids. Scaffold 1 was not designed to mimic any particular secondary structure, but simulated accessible conformations of this material were compared with common ideal secondary structures and with >125,000 different protein-protein interaction (PPI) interfaces. This data mining exercise indicates that scaffolds 1 can mimic features of sheet-turn-sheets, somewhat fewer helical motifs, and numerous PPI interface regions that do not resemble any particular secondary structure.
• A Multifaceted Secondary Structure Mimic Based On Piperidine-piperidinones
  作者：Dongyue Xin、Lisa M. Perez、Thomas R. Ioerger、Kevin Burgess

  DOI：10.1002/anie.201400927

  日期：2014.4.1

  that with ideal secondary structures and real interface regions in PPIs. Scaffold 1 presents amino acid side‐chains that are quite separated from each other, in orientations that closely resemble ideal sheet or helical structures, similar non‐ideal structures at PPI interfaces, and regions of other PPI interfaces where the mimic conformation does not resemble any secondary structure. 68 different PPIs

  极简二级结构模拟物通常被制成类似于蛋白质-蛋白质相互作用 (PPI) 中的一个界面，从而扰乱它。我们最近提出合适的化学型可以直接与界面区域匹配，而无需考虑二级结构。在这里，我们描述了新化学型1的模块化合成，其溶液态构象集合的模拟，以及与理想二级结构和 PPI 中真实界面区域的相关性。脚手架1呈现彼此完全分离的氨基酸侧链，其方向与理想的片状或螺旋结构非常相似，在 PPI 界面具有相似的非理想结构，以及其他 PPI 界面的模拟构象与任何二级结构不相似的区域. 68 种不同的 PPI，其中1 个匹配孔的构象被识别。还提出了一种新方法来确定极简模拟晶体结构与其溶液构象的相关性。因此，dld - 1 faf以比最小能量溶液状态高0.91 kcal mol -1的构象结晶。
• Synthesis of Enantiopure 4-Hydroxypipecolate and 4-Hydroxylysine Derivatives from a Common 4,6-Dioxopiperidinecarboxylate Precursor
  作者：J. Marin、C. Didierjean、A. Aubry、J.-R. Casimir、J.-P. Briand、G. Guichard

  DOI：10.1021/jo0353886

  日期：2004.1.1

  tert-Butyl 2-substituted 4,6-dioxo-1-piperidinecarboxylates 4 have been prepared in good yield starting from Boc-Asp-(OBu)-Bu-t and other beta-amino acids. By analogy with chiral tetramic acids, their reduction by NaBH4 in CH2Cl2/AcOH afforded the corresponding cis-4-hydroxy delta-lactams in good yield and stereoselectivity (68-98% de). In the absence of the A(1,3) strain (reduction of 6-substituted 2,4-dioxo-1-piperidines 7), the cis-4-hydroxy isomer was still obtained as the major product but the de values were consistently lower. 4-Hydroxy-6-oxo-1,2-piperidinedicarboxylate 2a, readily accessible from Boc-Asp-OtBu (three steps, 63% overall yield), has proven to be an excellent building block for the synthesis of cis- and trans-4-hydroxypipecolates 17 and 24 (52 and 36% overall yield, respectively) and for the synthesis of a protected 4-hydroxylysine derivative 29 (41% overall yield).