4,5-dimethoxycarbonyl-2(1H)-pyridone | 80658-29-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4,5-dimethoxycarbonyl-2(1H)-pyridone
• 英文别名: 4,5-bis(methoxycarbonyl)-2-pyridone；dimethyl 6-oxo-1H-pyridine-3,4-dicarboxylate
• CAS: 80658-29-3
• 化学式: C₉H₉NO₅
• 分子量: 211.174
• InChiKey: ZIPUQSTXRXYKDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.05
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  85.46
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4,5-dimethoxycarbonyl-2(1H)-pyridone 、 对甲苯磺酰氯 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以84%的产率得到Dimethyl 1-(4-methylphenyl)sulfonyl-6-oxopyridine-3,4-dicarboxylate
  参考文献：
  名称：

  Diels-Alder Reaction of 2-Pyridones Having an Acyl or a Sulfonyl Group on Nitrogen

  摘要：

  Diels-Alder (DA) reaction of 5-methoxycarbonyl-2-pyridone, which has an electron-withdrawing acyl group at nitrogen, with 1,3-diene afforded 2-quinolone derivatives in modest yields. Further, DA reaction of 5,4-dimethoxycarbonyl-1-sulfonyl-2-pyridone gave 2-quinolone and 1-isoquinolone (1:1). DA reaction of 2-sulfonyl-1-isoquinolone afforded a functionalized phenanthridone. The site-selectivity was well correlated with the corresponding activation energies calculated using an ab initio molecular orbital method.

  DOI：

  10.3987/com-08-s(f)4
• 作为产物：
  描述：

  3,4-bis(methoxycarbonyl)pyridin-1-ium-1-olate 在 乙酸酐 作用下， 以12%的产率得到4,5-dimethoxycarbonyl-2(1H)-pyridone
  参考文献：
  名称：

  （E）-β-烯胺酰胺与乙酰二羧酸二甲酯（DMAD）的反应：苯衍生物，烯胺酯和2-吡啶酮的形成

  摘要：

  （的加法调查ë）-enamino酰胺（1A - d）与DMAD已经表明，它们是由中间体的立体化学和烯胺系统的胺成分的影响。在干乙腈中，（E）-苄基（甲基）氨基-（1b），（E）-吡咯烷-1-基氨基-（1c）和（E）-哌啶-1-基氨基-（1d）丙烯酰胺，得到四甲基苯-1,2,3,4-四羧酸酯（5），（E）-氨基丁烯二酸酯（6b - d）和3,4-双甲氧基羰基吡啶-2-（1 H）-一8）。由于β-碳的不同亲核性，二甲氨基-（1a）和吗啉-1-基氨基-（1e）-丙烯酰胺形成了两性离子（11），该两性离子消除了丙醇酰胺，仅得到（E）-氨基丁烯二酸酯（6a，e）。

  DOI：

  10.1039/p19890001007

文献信息

• Correlations between carbon-13 nuclear magnetic resonance chemical shifts and reactivities of siloxybutadienes and siloxyazabutadienes in the Diels-Alder reaction with dimethyl acetylenedicarboxylate.
  作者：Jun-etsu IGARASHI、Yoshinari KAWAKAMI、Toshio KINOSHITA、Sunao FURUKAWA

  DOI：10.1248/cpb.38.1832

  日期：——

  In the reaction of silylated butadiene derivatives (1) with dimethyl acetylenedicarboxylate (DMAD), it is proposed that the reactivities of the dienes can be predicted from the carbon-13 nuclear magnetic resonance chemical shifts of the terminal methylene carbons (δ13C-4) of the dienes based on the following linear relationships, a) total electron densities against δ13C-4; b) ln k against 1/[ELUMO(DMAD)-EHOMO(diene)]; c) ln k against δ13C-4. The total electron densities and energy levels of highest occupied molecular orbitals (HOMOs) and lowest unoccupied molecular orbitals (LUMOs) of the dienes were calculated by the modified neglect of diatomic overlap (MNDO) method.

  在硅烷化丁二烯衍生物 (1) 与乙炔二甲酸二甲酯（DMAD）的反应中，建议根据二烯末端亚甲基碳（δ13C-4）的碳-13 核磁共振化学位移，按照以下线性关系预测二烯的反应活性：a) 总电子密度与δ13C-4 的关系；b) ln k 对 1/[ELUMO（DMAD）-EHOMO（二烯）]； c) ln k 对 δ13C-4。二烯的总电子密度以及最高占位分子轨道（HOMOs）和最低未占位分子轨道（LUMOs）的能级是通过修正的忽略二原子重叠（MNDO）法计算得出的。
• A highly efficient multicomponent synthesis of pyridones and pyrimidones by a [2+2+2] strategy
  作者：Lon Ghosez、Eric Jnoff、Philippe Bayard、Francy Sainte、Renaud Beaudegnies

  DOI：10.1016/s0040-4020(98)01149-1

  日期：1999.3

  :The reaction of N-silylated iminoethers with 2-substituted acetyl chlorides yields activated 2-azadienes. These were shown to react with electron-deficient acetylenic dienophiles to yield pyridones. They also react with quinones to give the corresponding aromatized cycloadducts in good yields. The reaction of a-azadienes with activated nitriles provided a very practical route towards polysubstituted pyrimidones. A multicomponent protocol is reported which combines a N-t-butyldimethylsilyl iminoether, an acetyl chloride derivative and a dienophile in the presence of triethylamine without isolation of any intermediate. This provides an extremely practical and versatile route to various mono- and polycyclic azaaromatics with a predictable substitution pattern. Yields ranged from 43 % to 94 % for the complete sequence. (C) 1999 Elsevier Science Ltd. All rights reserved.
• A Diels-Alder route to pyridone and piperidone derivatives
  作者：Francy Sainte、Beatrice Serckx-Poncin、Anne Marie Hesbain-Frisque、Leon Ghosez

  DOI：10.1021/ja00369a049

  日期：1982.3
• NUVOLE, ANTONIO;PAGLIETTI, GIUSEPPE, J. CHEM. SOC. PERKIN TRANS. PT 1,(1989) N, C. 1007-1011
  作者：NUVOLE, ANTONIO、PAGLIETTI, GIUSEPPE

  DOI：——

  日期：——
• SAINTE, F.;SERCKS-PONCIN, B.;HESBAIN-FRISQUE, A. -M.;GHOSEZ, L., J. AMER. CHEM. SOC., 1982, 104, N 5, 1428-1430
  作者：SAINTE, F.、SERCKS-PONCIN, B.、HESBAIN-FRISQUE, A. -M.、GHOSEZ, L.

  DOI：——

  日期：——