3-formyl-4-hydroxy-6-methylpyridin-2(1H)-one | 66620-83-5

• 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: 3-formyl-4-hydroxy-6-methylpyridin-2(1H)-one
• 英文别名: 4-hydroxy-6-methyl-2-oxo-1,2-dihydro-pyridine-3-carbaldehyde；3-Pyridinecarboxaldehyde, 1,2-dihydro-4-hydroxy-6-methyl-2-oxo-；4-hydroxy-6-methyl-2-oxo-1H-pyridine-3-carbaldehyde
• CAS: 66620-83-5
• 化学式: C₇H₇NO₃
• mdl: MFCD01851085
• 分子量: 153.137
• InChiKey: ZREYDDIQAZXMOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-formyl-4-hydroxy-6-methylpyridin-2(1H)-one 在 哌啶 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 56.0h， 生成 3-(2-aminoacetyl)-7-methyl-2H-pyrano[3,2-c]pyridine-2,5(6H)-dione
  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
• 作为产物：
  描述：

  2,4-二羟基-6-甲基吡啶 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 1.5h， 生成 3-formyl-4-hydroxy-6-methylpyridin-2(1H)-one
  参考文献：
  名称：

  一些取代的 2H-吡喃并[3,2-c]吡啶-2,5(6H)-二酮的合成。它们的 3-乙酰基衍生物与 3-氨基-2-丁烯酸甲酯的反应

  摘要：

  摘要 4-羟基-6-甲基-2(1H)-吡啶酮的甲酰化和随后用维蒂希试剂或CH-酸酯环化得到一系列标题化合物。相同的起始吡啶酮与 3-氨基-2-丁烯酸甲酯直接反应生成相应的 4,7-二甲基吡喃并 [3,2-c] 吡啶。

  DOI：

  10.1080/00397919808007006

文献信息

• Sassa, Takeshi; Uchie, Kazumi; Kato, Hideyuki, Agricultural and Biological Chemistry, 1987, vol. 51, # 1, p. 271 - 272
  作者：Sassa, Takeshi、Uchie, Kazumi、Kato, Hideyuki、Onuma, Yukio

  DOI：——

  日期：——
• COMPOUNDS FOR THE TREATMENT OF INFLAMMATORY DISORDERS
  申请人：Tong Ling

  公开号：US20120015926A1

  公开（公告）日：2012-01-19

  This invention relates to compounds of the Formula (I): (Chemical formula should be inserted here as it appears on abstract in paper form) (I) or a pharmaceutically acceptable salt thereof, which can be useful for the treatment of diseases or conditions mediated by MMPs, ADAMs, TACE, aggrecanase, TNF- or combinations thereof.
• 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
  作者：Duy Hua、Allan Prior、Medha Gunaratna、Daisuke Kikuchi、John Desper、Yunjeong Kim、Kyeong-Ok Chang、Izumi Maezawa、Lee-Way Jin

  DOI：10.1055/s-0033-1339027

  日期：——

  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.
• Synthesis of Some Substituted 2<i>H</i>-Pyrano[3,2-<i>c</i>]pyridine-2,5(6<i>H</i>)-diones. Reaction of Their 3-Acetyl Derivatives with Methyl 3-Amino-2-butenoate
  作者：Edmont V. Stoyanov、Ivo C. Ivanov

  DOI：10.1080/00397919808007006

  日期：1998.5

  Formylation of 4-hydroxy-6-methyl-2(1H)-pyridones and subsequent cyclization with a Wittig reagent or with CH-acidic esters gave a series of title compounds. The same starting pyridones reacted with methyl 3-amino-2-butenoate directly to the corresponding 4,7-dimethylpyrano[3,2-c]pyridines.

  摘要 4-羟基-6-甲基-2(1H)-吡啶酮的甲酰化和随后用维蒂希试剂或CH-酸酯环化得到一系列标题化合物。相同的起始吡啶酮与 3-氨基-2-丁烯酸甲酯直接反应生成相应的 4,7-二甲基吡喃并 [3,2-c] 吡啶。