N-(5-acetyl-6-methyl-2-oxo-2H-pyran-3-yl)acetamide | 925933-03-5

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(5-acetyl-6-methyl-2-oxo-2H-pyran-3-yl)acetamide
• 英文别名: 3-acetylamino-6-methyl-2H-pyran-2-one；N-(5-acetyl-6-methyl-2-oxopyran-3-yl)acetamide
• CAS: 925933-03-5
• 化学式: C₁₀H₁₁NO₄
• 分子量: 209.202
• InChiKey: HLBAQHORDIISHW-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C(Solv: ethanol (64-17-5))
• 沸点：
  423.1±45.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  72.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(5-acetyl-6-methyl-2-oxo-2H-pyran-3-yl)acetamide 在 sodium azide 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以86%的产率得到N-[3-acetylamino-6-methyl-2-oxo-2H-pyran-5-yl]acetamide
  参考文献：
  名称：

  Pozgan, Franc; Krejan, Maja; Polanc, Slovenko, Heterocycles, 2006, vol. 69, # 1, p. 123 - 132

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(5-acetyl-6-methyl-2-oxo-2H-pyran-3-yl)-benzamide 在 硫酸 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(5-acetyl-6-methyl-2-oxo-2H-pyran-3-yl)acetamide
  参考文献：
  名称：

  Pozgan, Franc; Krejan, Maja; Polanc, Slovenko, Heterocycles, 2006, vol. 69, # 1, p. 123 - 132

  摘要：

  DOI：

文献信息

• Ethyl Vinyl Ether as a Synthetic Equivalent of Acetylene in a DABCO-Catalyzed Microwave-Assisted Diels-Alder-Elimination Reaction Sequence Starting from 2<i>H</i>-Pyran-2-ones
  作者：Krištof Kranjc、Marijan Kočevar

  DOI：10.1055/s-0028-1083515

  日期：——

  We present a study of the Diels-Alder reaction between various electron-deficient 2H-pyran-2-ones and ethyl vinyl ether. This microwave-accelerated sequence of a cycloaddition followed by a retro-Diels-Alder reaction (the elimination of CO 2 ) and a second elimination step ofEtOH yields substituted aniline derivatives. The reaction sequence is greatly accelerated by the application of DABCO as a suitable

  我们研究了各种缺电子 2H-pyran-2-ones 与乙基乙烯基醚之间的 Diels-Alder 反应。这种微波加速的环加成顺序，随后是逆狄尔斯-阿尔德反应（CO 2 的消除）和EtOH的第二个消除步骤，产生取代的苯胺衍生物。使用 DABCO 作为合适的碱大大加快了反应顺序。
• The Participation of 2H-Pyran-2-ones in [4+2] Cycloadditions: An Experimental and Computational Study
  作者：Bogdan Štefane、Andrej Perdih、Andrej Pevec、Tomaž Šolmajer、Marijan Kočevar

  DOI：10.1002/ejoc.201000236

  日期：2010.10

  carboxylic substituents on the dienophiles 10 and 11 shifts the DA reaction with 2H-pyran-2-ones to a less polar and more synchronous concerted reaction mechanism. Calculated CT as well as values of the global electrophilicity ω and nucleophilicity N indexes revealed that 2H-pyran-2-ones act in this case as nucleophiles and reacting dienophiles 10 and 11 as electrophiles. The results are consistent with

  对一系列 2H-吡喃-2-酮 1 和非对称取代的炔烃 2、10 和 11 的 Diels-Alder (DA) 反应机理进行了实验和计算 DFT 研究。几个 2H-pyran-2-ones 1 用 N,N-二乙基丙炔胺 (2) 处理。结果指向极性和异步两步机制，符合极性 Diels-Alder (P-DA) 反应机制的特点。[5] 在 1 与 2 反应过程中意外形成的少量产物 4a-d 可以通过考虑新形成的 CC 键周围容易通过的扭转势垒来合理化，该扭转势垒能够实现两种不同的环化模式。电荷转移 (CT) 和全局反应性指数分析表明，在这些反应中，2H-pyran-2-ones 作为亲电子试剂和 N，N-二乙基丙胺 (2) 作为亲核试剂反应伙伴。在亲二烯体 10 和 11 上引入吸电子羧基取代基将 DA 与 2H-吡喃-2-酮的反应转变为极性较小且更同步的协同反应机制。计算的 CT 以及全局亲电性
• Comparison of the reaction pathways and intermediate products of a microwave-assisted and high-pressure-promoted cycloaddition of vinyl-moiety-containing dienophiles on 2H-pyran-2-ones
  作者：Amadej Juranovič、Krištof Kranjc、Franc Perdih、Slovenko Polanc、Marijan Kočevar

  DOI：10.1016/j.tet.2011.03.034

  日期：2011.5

  A comparative study of the reaction pathway of the cycloaddition of various vinyl-containing dienophiles on a set of substituted 3-acylamino-2H-pyran-2-ones under microwave-assisted and high-pressure conditions is presented. In the course of the reaction both the intermediate products, i.e., the 2-oxabicyclo[2.2.2]oct-5-ene (the exo/endo selectivity depended upon the dienophile) and the alkoxycyclohexadiene systems, were isolated and comprehensively characterized; this included X-ray diffraction analyses. The role of the base (DABCO) as an organocatalyst was further elucidated. (C) 2011 Elsevier Ltd. All rights reserved.
• An expeditious synthesis of β-pyrimidyl-α,β-didehydro-α-amino acid derivatives and pyrano[2,3-d]pyrimidines using microwave-assisted conditions
  作者：Jure Hren、Franc Požgan、Alma Bunič、Vasile I. Parvulescu、Slovenko Polanc、Marijan Kočevar

  DOI：10.1016/j.tet.2009.07.072

  日期：2009.9

  An expeditious transformation of 5-acyl-2H-pyran-2-ones with various amidines as 1,3-binucleophiles into isomerically pure (E)-alpha,beta-diclehyrdro-alpha-amino acid derivatives (DDAAD) containing the 5-pyrimidyl moiety at the beta-position is described. The method was performed in ethanolic (or ethanol/water) solutions in the presence of Na2CO3 as a nontoxic base and under microwave-assisted conditions. When starting from the 5-ethoxycarbonyl-2H-pyran-2-one derivative and in the presence of DBU as a base the corresponding pyrano[2,3-d]pyrimidines were prepared. (C) 2009 Elsevier Ltd. All rights reserved.
• A 26-Membered Macrocycle Obtained by a Double Diels–Alder Cycloaddition Between Two 2H-Pyran-2-one Rings and Two 1,1'-(Hexane-1,6-diyl)bis (1H-pyrrole-2,5-dione)s
  作者：Bor Lucijan Turek、Marijan Kočevar、Krištof Kranjc、Franc Perdih

  DOI：10.17344/acsi.2017.3566

  日期：2017.12.15

  With the application of a double dienophile 1,1'-(hexane-1,6-diyl) bis(1H-pyrrole-2,5-dione) for a [4+2] cycloaddition with a substituted 2H-pyran-2-one a novel 26-membered tetraaza heteromacrocyclic system 3 was prepared via a direct method under solvent-free conditions with microwave irradiation. The macrocycle prepared is composed of two units of the dienophile and two of the diene. The structure of the macrocycle was characterized on the basis of IR, H-1 and C-13 NMR and mass spectroscopy, as well as by the elemental analysis and melting point determination. With X-ray diffraction of a single crystal of the macrocycle we have determined that the two acetyl groups (attached to the bridging double bond of the bicyclo[2.2.2] octene fragments) are oriented towards each other (and also towards the inside of the cavity of the macrocycle), therefore, mostly filling it completely.