3-乙酰基-4,6-二甲基-2(1H)-吡啶酮 | 16151-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 3-乙酰基-4,6-二甲基-2(1H)-吡啶酮
• 英文名称: 3-acetyl-4,6-dimethyl-2-pyridone
• 英文别名: 3-acetyl-4,6-dimethylpyridin-2(1H)-one；3-acetyl-4,6-dimethyl-2(1H)-pyridone；3-Acetyl-4,6-dimethyl-2(1H)-pyridon；3-acetyl-4,6-dimethyl-1H-pyridin-2-one
• CAS: 16151-14-7
• 化学式: C₉H₁₁NO₂
• mdl: MFCD00775755
• 分子量: 165.192
• InChiKey: FPZYYMHZCULYSO-UHFFFAOYSA-N

物化性质

• 熔点：
  218-219 °C
• 沸点：
  381.2±42.0 °C(Predicted)
• 密度：
  1.095±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-乙酰基-4,6-二甲基-2(1H)-吡啶酮 在 硫酸 、 lithium hydride 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 生成 5,7-dimethyl-2-trifluoromethyl-4H-pyrano[2,3-b]pyridin-4-one
  参考文献：
  名称：

  The first synthesis of 8-aza-2-polyfluoroalkylchromones

  摘要：

  The condensation of 3-acetyl-4,6-dimethyl-2-pyridone with RFCO2Et in the presence of LiH in dioxane affords corresponding R-F-containing beta-diketones, whose dehydration under the action of conc. H2SO4 gives 8-aza-5,7-dimethyl-2-polyfluoroalkylchromones. (C) 2002 Elsevier Science B.V. All rights reserved.

  DOI：

  10.1016/s0022-1139(02)00280-4
• 作为产物：
  描述：

  5,7-dimethyl-2-trifluoromethyl-4H-pyrano[2,3-b]pyridin-4-one 在 1,3-丙二胺 作用下， 以 四氢呋喃 为溶剂， 生成 3-乙酰基-4,6-二甲基-2(1H)-吡啶酮
  参考文献：
  名称：

  摘要：

  On treatment with ammonia, primary amines, and pyrrolidine, 5,7-dimethyl-2-trifluoromethyl-8-azachromone undergoes ring opening to give beta-aminovinyl ketones. The reactions with morpholine and piperidine proceed as addition to give 2-morpholino- and 2-piperidino-8-azachromanones. With ethylene diamine, diethylenetriamines, hydrazine hydrate, and hydroxylamine, this compound reacts similarly to 2-polyfluoroalkylchromones, yielding CF3-containing dihydrodiazepines, pyrazoles, and isoxazoles,with a 2-pyridone substituent.

  DOI：

  10.1023/a:1026000619881

文献信息

• Pyridine and pyrimidine ring syntheses from 4-(4-morpholino)-3-pentenone and from ethyl 3-(4-morpholino)-2-butenoate
  作者：Elaref S. Ratemi、Nivedita Namdev、Martin S. Gibson

  DOI：10.1002/jhet.5570300609

  日期：1993.12

  3-Substituted 2(1H)-pyridones are produced from reaction of 4-(4-morpholino)-3-pentenone 1 with each of the following carbon acids: cyanoacetamide, malononitrile, cyanothioacetamide, acetylacetamide, benzoyl-acetonitrile. Reaction of ethyl 3-(4-morpholino)-2-butenoate 2 with cyanoacetamide gives the corresponding hydroxypyridone. Pyrimidines are formed by reaction of 1 and of 2 with benzamidine and with S-benzylthio-urea;

  由4-（4-吗啉代）-3-戊烯酮1与以下每种碳酸反应生成3-取代的2（1 H）-吡啶酮：氰基乙酰胺，丙二腈，氰基硫代乙酰胺，乙酰基乙酰胺，苯甲酰基-乙腈。3-（4-吗啉代）-2-丁烯酸乙酯2与氰基乙酰胺反应，得到相应的羟基吡啶酮。嘧啶是通过1和2与苄am和S-苄硫脲反应形成的; 在最后一种情况下，消除的吗啉取代了苄硫基，得到了最终产物。
• 3-(Polyhaloacyl)chromones and their Hetero Analogues: Synthesis and Reactions with Amines
  作者：Vyacheslav Sosnovskikh、Roman Irgashev、Mikhail Barabanov

  DOI：10.1055/s-2006-942508

  日期：2006.8

  2-Hydroxy-2-(polyhaloalkyl)chroman-4-ones react with diethoxymethyl acetate at 140-150 °C for 15 minutes to give 3-(polyhaloacyl)chromones in good yields. The reactions of these compounds with amines proceeds at C-2 with pyrone ring-opening and formation of 2-(alkyl/arylaminomethylene)-2-hydroxy-2-(polyfluoroalkyl)chroman-4-ones.

  2-Hydroxy-2-(polyhaloalkyl)chroman-4-ones 与乙酸二乙氧基甲酯在 140-150 °C 下反应 15 分钟，以良好的收率得到 3-(polyhaloacyl)chromones。这些化合物与胺的反应在 C-2 进行，吡喃酮开环并形成 2-(烷基/芳基氨基亚甲基)-2-羟基-2-(多氟烷基)色满-4-酮。
• A Novel Redox Reaction between 8-Aza-5,7-dimethyl-2-trifluoromethylchromone and Alkyl Mercaptoacetates. Facile Synthesis of CF₃-Containing 2-Pyridone Derivatives
  作者：Vyacheslav Ya. Sosnovskikh、Mikhail A. Barabanov、Boris I. Usachev

  DOI：10.1021/jo049117m

  日期：2004.11.1

  8-Aza-5,7-dimethyl-2-trifluoromethylchromone reacts with alkyl mercaptoacetates in the presence of triethylamine to give pyrido derivatives of 2-oxa-7-thiabicyclo[3.2.1]octane, which undergo the reductive ring opening to alkyl 2-[3-(4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)-3-oxo-1-(trifluoromethyl)propyl]sulfanyl}acetates.The latter can be also obtained directly from 8-aza-5,7-dimethyl-2-trifluoromethylchromone

  8-Aza-5,7-二甲基-2-三氟甲基色酮在三乙胺的存在下与巯基乙酸烷基酯反应，生成2-oxa-7-硫代双环[3.2.1]辛烷的吡啶基衍生物，该衍生物经还原性开环反应成烷基2 -[[3-（4,6-二甲基-2-氧代-1,2-二氢吡啶基-3-基）-3-氧代-1-（三氟甲基）丙基]硫烷基}乙酸酯。后者也可以直接从8-氮杂5,7-二甲基-2-三氟甲基色酮，表现为被掩盖的α，β-不饱和酮，4,6-二甲基-3-（4,4,4-三氟丁-2-烯酰基）吡啶-2（ 1 H）-一。该化合物是由3-乙酰基-4,6-二甲基-2-吡啶酮独立合成的，并对其合成潜力进行了研究。已经以良好至中等的产率制备了多种包含CF 3基团的2-吡啶酮衍生物。
• The structure of products of phenacylation and subsequent (re)cyclizations of 3-acetyl-4,6-dimethylpyridin-2(1H)-one according to X-ray structural analysis
  作者：Ekaterina M. Okul’、Victor B. Rybakov、Eugene V. Babaev

  DOI：10.1007/s10593-017-2161-2

  日期：2017.9

  first time, where isomeric O- and N-substitution products were formed which then underwent cyclization under basic conditions with the formation of furo[2,3-b]pyridine and indolizin-5-one. Cyclization of the N-isomer under acidic conditions lead to an [1,3]oxazolo[3,2-a]pyridin-1-ium salt, which transformed into 5-morpholinoindolizine by the action of morpholine, and into oxazolylpyridine by the action

  首次描述了乙酰吡啶酮的新型苯甲酰化反应，形成了异构的O-和N-取代产物，然后在碱性条件下进行环化，形成呋喃[2,3- b ]吡啶和吲哚嗪-5。 -一。N-异构体在酸性条件下的环化反应产生[1,3]恶唑并[3,2 - a ]吡啶-1-鎓盐，该盐在吗啉作用下转化为5-吗啉代吲哚嗪，在该作用下转化为恶唑基吡啶氨 通过X射线结构分析确定产物的结构。
• Use of Cinnamoyl Compound
  申请人：Shiraki Hiroaki

  公开号：US20090143368A1

  公开（公告）日：2009-06-04

  A composition for inhibiting the extracellular matrix gene transcription comprising a cinnamoyl compound represented by the formula (I): and an inert carrier, or the like.

  一种用于抑制细胞外基质基因转录的组合物，包括由式（I）表示的肉桂酰化合物和惰性载体等。