3-氧代-N-2-吡啶基丁酰胺 | 1657-28-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 中文名称: 3-氧代-N-2-吡啶基丁酰胺
• 英文名称: 3-oxo-N-(pyrid-2-yl)butyramide
• 英文别名: 3-oxo-N-(2-pyridyl)butanamide；3-Oxo-N-2-pyridylbutyramide；3-oxo-N-pyridin-2-ylbutanamide
• CAS: 1657-28-9
• 化学式: C₉H₁₀N₂O₂
• mdl: MFCD00023427
• 分子量: 178.191
• InChiKey: JSYFBSLKZLDZOC-UHFFFAOYSA-N

物化性质

• 熔点：
  113 °C
• 沸点：
  407.8±25.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.222
• 拓扑面积：
  59.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933399090
• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  3-氧代-N-2-吡啶基丁酰胺 在 硫酸 作用下， 生成 2-甲基-4H-吡啶并[1,2-a]嘧啶-4-酮
  参考文献：
  名称：

  119.杂环化合物的新合成。第十二部分。β-氨基巴豆酸乙酯与某些环am的缩合

  摘要：

  DOI：

  10.1039/jr9510000551
• 作为产物：
  描述：

  2-氨基吡啶 、 乙酰乙酸甲酯 在 六氟异丙醇 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以75%的产率得到3-氧代-N-2-吡啶基丁酰胺
  参考文献：
  名称：

  HFIP介导的针对β-氧代酰胺的策略，以及随后使用可循环利用的催化剂将Friedel-Craft型环化为2-喹啉酮

  摘要：

  以胺和β-酮酸酯为底物，描述了一种简单且经济高效的1,1,1,3,3,3-六氟-2-丙醇（HFIP）介导的合成β-氧代酰胺的方案。发现反应条件对于裂解CO键和由此以优异的产率和选择性形成产物是高度有效的。将所得到的β氧代酰胺在被进一步转化为合成有用2-喹啉酮通过芳族环的分子内弗里德尔-工艺类型环化使用铁氧体作为可回收催化剂。在反应条件下，具有多种官能团的底物的光谱被很好地耐受。文献和质谱证据充分验证了所提出的机制途径。

  DOI：

  10.1016/j.tetlet.2020.152535

文献信息

• Facile eco-friendly synthesis of novel chromeno[4,3-b]pyridine-2,5-diones and evaluation of their antimicrobial and antioxidant properties
  作者：SATYANARAYANA REDDY JAGGAVARAPU、ANAND SOLOMON KAMALAKARAN、VENTKATA PRASAD JALLI、SRAVAN KUMAR GANGISETTY、MUNUSSWAMY RAMANUJAM GANESH、GOPIKRISHNA GADDAMANUGU

  DOI：10.1007/s12039-013-0565-9

  日期：2014.1

  broad spectrum antibacterial properties against all the evaluated bacteria, compound 5g exhibited good antioxidant properties. Tricyclic chromeno[4,3-b]pyridine-2,5-diones are precipitated as pure products from the reaction of 4-chloro-3-formyl-coumarin and acetoacetamides in PEG-300 as recyclable solvent and evaluated for their antimicrobial and antioxidant properties.

  通过4-氯-3-甲酰基香豆素和乙酰乙酰胺在可回收溶剂中的4-氯-3-甲酰基香豆素和乙酰乙酰胺的温和碱催化反应，可以快速，轻松地获得新的铬[4,3-b]吡啶-2,5-二酮衍生物。在控制头孢噻肟的情况下，评估了这些化合物对3种革兰氏阳性和3种革兰氏阴性细菌（表皮葡萄球菌，副溶血弧菌，枯草芽孢杆菌，大肠杆菌，金黄色葡萄球菌和肺炎克雷伯菌）的抗菌活性。他们使用抗坏血酸对照的DPPH测试对他们进行了抗氧化剂研究。而化合物5d和5k对所有评估细菌显示出广阔的抗菌前景，化合物5g表现出良好的抗氧化特性。 从4-氯-3-甲酰基香豆素和乙酰乙酰胺在PEG-300中作为可循环溶剂的反应，以纯产物形式沉淀出三环chromeno [4,3-b]吡啶-2,5-二酮，并对其抗菌性和抗氧化剂进行了评估属性。
• The Specificity and Broad Multitarget Properties of Ligands for the Free Fatty Acid Receptors FFA3/GPR41 and FFA2/GPR43 and the Related Hydroxycarboxylic Acid Receptor HCA2/GPR109A
  作者：Egils Bisenieks、Brigita Vigante、Ramona Petrovska、Baiba Turovska、Ruslan Muhamadejev、Vitalijs Soloduns、Astrida Velena、Karlis Pajuste、Luciano Saso、Janis Klovins、Gunars Duburs、Ilona Mandrika

  DOI：10.3390/ph14100987

  日期：——

  The paradigm of ligand-receptor interactions postulated as “one compound—one target” has been evolving; a multi-target, pleiotropic approach is now considered to be realistic. Novel series of 1,4,5,6,7,8-hexahydro-5-oxoquinolines, pyranopyrimidines and S-alkyl derivatives of pyranopyrimidines have been synthesized in order to characterise their pleiotropic, multitarget activity on the FFA3/GPR41, FFA2/GPR43, and HCA2/GPR109A receptors. Hexahydroquinoline derivatives have been known to exhibit characteristic activity as FFA3/GPR41 ligands, but during this study we observed their impact on FFA2/GPR43 and HCA2/GPR109A receptors as well as their electron-donating activity. Oxopyranopyrimidine and thioxopyranopyrimidine type compounds have been studied as ligands of the HCA2/GPR109A receptor; nevertheless, they exhibited equal or higher activity towards FFA3/GPR41 and FFA2/GPR43 receptors. S-Alkyl derivatives of pyranopyrimidines that have not yet been studied as ligands of GPCRs were more active towards HCA2/GPR109A and FFA3/GPR41 receptors than towards FFA2/GPR43. Representative compounds from each synthesized series were able to decrease the lipopolysaccharide-induced gene expression and secretion of proinflammatory cytokines (IL-6, TNF-α) and of a chemokine (MCP-1) in THP-1 macrophages, resembling the effect of HCA2/GPR109A ligand niacin and the endogenous ligand propionate. This study revealed groups of compounds possessing multitarget activity towards several receptors. The obtained data could be useful for further development of multitarget ligands.

  配体-受体相互作用范式被提出为“一个化合物-一个靶标”，正在演变；多靶点、多效应途径现在被认为是现实的。为了表征它们在FFA3/GPR41、FFA2/GPR43和HCA2/GPR109A受体上的多效应、多靶点活性，已经合成了新的1,4,5,6,7,8-六氢-5-氧喹啉、吡喃吡嘧啶和吡喃吡嘧啶的S-烷基衍生物系列。已知六氢喹啉衍生物表现出作为FFA3/GPR41配体的特征活性，但在这项研究中，我们观察到它们对FFA2/GPR43和HCA2/GPR109A受体的影响，以及它们的电子给体活性。氧代吡喃吡嘧啶和硫代吡喃吡嘧啶类化合物已被研究为HCA2/GPR109A受体的配体；然而，它们表现出对FFA3/GPR41和FFA2/GPR43受体相同或更高的活性。尚未作为GPCR配体研究的吡喃吡嘧啶的S-烷基衍生物对HCA2/GPR109A和FFA3/GPR41受体的活性比对FFA2/GPR43更高。每个合成系列的代表性化合物能够降低THP-1巨噬细胞中脂多糖诱导的炎症细胞因子（IL-6、TNF-α）和趋化因子（MCP-1）的基因表达和分泌，类似于HCA2/GPR109A配体烟酸和内源性配体丙酸的作用。这项研究揭示了一些具有多靶点活性的化合物群。获得的数据对于进一步开发多靶点配体可能是有用的。
• Intramolecular hydrogen bonding-assisted cyclocondensation of α-diazoketones with various amines: a strategy for highly efficient Wolff 1,2,3-triazole synthesis
  作者：Zikun Wang、Xihe Bi、Peiqiu Liao、Rui Zhang、Yongjiu Liang、Dewen Dong

  DOI：10.1039/c2cc33157h

  日期：——

  A catalytic and highly efficient Wolff's cyclocondensation of α-diazoketones with aromatic and aliphatic amines has been realized for the first time by utilizing the strategy of an intramolecular hydrogen bonding-activating carbonyl group. This approach successfully solved the challenging problem of poor condensation efficiency in Wolff 1,2,3-triazole synthesis, and constitutes a powerful method for the synthesis of highly functionalized 1,2,3-triazoles.

  通过利用分子内氢键活化羰基的策略，实现了催化高效Wolff酮内α-重氮酮与芳香胺和脂肪胺的环化缩合反应，成功解决了Wolff型1,2,3-三氮唑合成中缩合效率低下的难题，成为合成高度功能化1,2,3-三氮唑的有力方法。
• Formal [4+1] annulation of α,α-dialkyl β-oxo amides and dimethylsulfoxonium methylide: a synthetic route to β-hydroxy-γ-lactams
  作者：Dingyuan Zhang、Qian Zhang、Ning Zhang、Rui Zhang、Yongjiu Liang、Dewen Dong

  DOI：10.1039/c3cc43317j

  日期：——

  A facile and efficient one-pot synthesis of β-hydroxy-γ-lactams from α,α-dialkyl β-oxo amides and trimethylsulfoxonium iodide in the presence of sodium hydride via a tandem Corey–Chaykovsky reaction and an intramolecular lactamization process is developed.

  开发了一种简便高效的一锅法合成β-羟基-γ-内酰胺的方法，该方法利用α,α-二烷基β-氧代酰胺与三甲基亚磺酰碘在氢化钠存在下通过串联的Corey-Chaykovsky反应和分子内内酰胺化过程合成。
• Acetoacetanilides as Masked Isocyanates: Facile and Efficient Synthesis of Unsymmetrically Substituted Ureas
  作者：Ying Wei、Jing Liu、Shaoxia Lin、Hongqian Ding、Fushun Liang、Baozhong Zhao

  DOI：10.1021/ol101474f

  日期：2010.10.1

  A general and practical method for the preparation of unsymmetrically substituted ureas has been developed. By the reactions of acetoacetanilides with various amines including primary/secondary amines, a series of substituted aryl ureas were achieved in high yields. Acetoacetanilide substrates can be considered as masked reagents that liberate reactive isocyanates in situ.

  已经开发了制备不对称取代的脲的通用且实用的方法。通过乙酰乙酰苯胺与各种胺（包括伯/仲胺）的反应，可以高收率获得一系列取代的芳基脲。乙酰乙酰苯胺底物可视为可在现场释放反应性异氰酸酯的掩蔽试剂。

表征谱图