4-羟基-6-甲基-3-硝基吡喃-2-酮 | 668-43-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 中文名称: 4-羟基-6-甲基-3-硝基吡喃-2-酮
• 英文名称: 4-hydroxy-6-methyl-3-nitro-2H-pyran-2-one
• 英文别名: 4-hydroxy-6-methyl-3-nitropyran-2-one
• CAS: 668-43-9
• 化学式: C₆H₅NO₅
• mdl: MFCD06653679
• 分子量: 171.109
• InChiKey: LNAAVFQZQXHCEW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.166
• 拓扑面积：
  92.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-羟基-6-甲基-3-硝基吡喃-2-酮 在 sodium azide 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 6-methyl-4-{[(1E)-1-morpholin-4-ylbutylidene]amino}-3-nitro-2H-pyran-2-one
  参考文献：
  名称：

  Synthesis of 4-dialkylaminopyridine derivatives through ring-rearrangement of 3-nitro-2H-pyran-2-one acetamidines

  摘要：

  A new synthesis of substituted 4-dialkylaminopyridines was developed, starting from 3-nitropyran-2-one N-functionalized amidines. Secondary amines were reacted with the amidines in a sealed tube and in ethanol as the solvent yielding exclusively 4-dialkylaminopyridine derivatives or a mixture with 4-methylpyridine derivative, depending on the C-alpha-linked substituents of the starting amidine. Structural elucidation of the 4-dialkylaminopyridines revealed their existence as two tautomeric forms, depending on the solvent. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.022
• 作为产物：
  描述：

  4-羟基-6-甲基-2-吡喃酮 在 硫酸 、 硝酸 作用下， 反应 0.67h， 以79%的产率得到4-羟基-6-甲基-3-硝基吡喃-2-酮
  参考文献：
  名称：

  Syntheses of 3-[(Alkylamino)methylene]-6-methylpyridine-2,4(1H,3H)-diones, 3-Substituted 7-Methyl-2H-pyrano[3,2-c]pyridine-2,5(6H)-dione Fluorescence Probes, and Tetrahydro-1H,9H-2,10-dioxa-9-azaanthracen-1-ones

  摘要：

  Various condensation and ring-closing reactions were used for the syntheses of 3-[(alkylamino)methylene]-6-methylpyri-dine-2,4(1H,3H)-diones, bicyclic pyridinones, and tricyclic morpholinopyrones. For instance, 3-[(dialkylamino)methylene]-6-methylpyridine-2,4(1H,3H)-diones were synthesized from the condensation of dialkylamines and 3-formyl-4-hydroxy-6-methylpyridin-2(1H)-one. 3-Formyl-4-hydroxy-6-methylpyridin-2(1H)-one, derived from 3-formyl-4-hydroxy-6-methylpyridin-2(1H)-one, was used to construct a number of bicyclic pyridinones via a one-pot Knoevenagal and intramolecular lactonization reaction. Tricyclic morpholinopyrones were assembled from a dialkylation reaction involving a dinucleophile, 3-amino-4-hydroxy-6-methyl-2H-pyran-2-one, and a dielectrophile, trans-3,6-dibromocyclohexene. Depending on the reaction conditions, isomers of the tricyclic molecules can be selectively produced, and their chemical structures were unequivocally determined using single-crystal X-ray analyses and 2D COSY spectroscopy. The fluorescently active bicyclic pyridinone compounds show longer absorption (368-430 nm; maximum) and emission wavelengths (450-467 nm) than those of 7-amino-4-methylcoumarin (AMC; λ_abs,max = 350 nm; λ_em = 430 nm) suggesting these molecules, such as 3-(2-aminoacetyl)-7-methyl-2H-pyrano[3,2-c]pyridine-2,5(6H)-dione, can be employed as fluorescence activity based probes for tracing biological pathways.

  DOI：

  10.1055/s-0033-1339027

文献信息

• Akhtar, Nahid; Munawar, M. A.; Siddiq, M., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1986, vol. 25, p. 328
  作者：Akhtar, Nahid、Munawar, M. A.、Siddiq, M.

  DOI：——

  日期：——
• Dallacker,F. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 643, p. 97 - 109
  作者：Dallacker,F. et al.

  DOI：——

  日期：——
• RADL, S.;HOUSKOVA, V.;ZIKAN, V., CS. FARM., 38,(1989) N, C. 219-222
  作者：RADL, S.、HOUSKOVA, V.、ZIKAN, V.

  DOI：——

  日期：——
• HIRSCH, B.;HOFGEN, N.
  作者：HIRSCH, B.、HOFGEN, N.

  DOI：——

  日期：——
• AKHTAR NAHID; MUNAWAR M. A.; SIDDIO M., INDIAN J. CHEM., 25,(1986) N 3, 328
  作者：AKHTAR NAHID、 MUNAWAR M. A.、 SIDDIO M.

  DOI：——

  日期：——