2,3,5,6-Tetramethyl-4H-pyran-4-one | 14901-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 2,3,5,6-Tetramethyl-4H-pyran-4-one
• 英文别名: 2,3,5,6-tetramethylpyran-4-one；2,3,5,6-tetramethyl-4-pyrone；tetramethyl-4-pyrone；tetramethyl-pyran-4-one；Tetramethyl-pyran-4-on；2,3,5,6-Tetramethyl-γ-pyron
• CAS: 14901-87-2
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: RMBZCEQCJKMJLB-UHFFFAOYSA-N

物化性质

• 熔点：
  90-91 °C(Solv: ligroine (8032-32-4))
• 沸点：
  154 °C(Press: 25 Torr)
• 密度：
  0.997±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,5,6-Tetramethyl-4H-pyran-4-one 以 水 为溶剂， 生成 2,3,4,5-tetramethyl-4,5-dihydroxycyclopent-2-enone
  参考文献：
  名称：

  Pavlik, James W.; Snead, Thomas E.; Tata, James R., Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1481 - 1483

  摘要：

  DOI：
• 作为产物：
  描述：

  3-戊酮 在 溶剂黄146 作用下， 反应 8.0h， 以46%的产率得到2,3,5,6-Tetramethyl-4H-pyran-4-one
  参考文献：
  名称：

  Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors

  摘要：

  Verticipyrone has recently been isolated from the culture broth of Verticillium sp. and shown to inhibit NADH fumarate reductase, as well as NADH oxidoreductase ( complex I) of the mitochondrial electron transport chain. In order to assess the structural elements in verticipyrone essential for complex I inhibitor, 15 structural analogues were prepared and analyzed for their effects on mitochondrial NADH oxidoreductase and NADH oxidase activities. Also measured were the abilities of several of the analogues to inhibit respiration as judged by a shift to glycolysis, and to inhibit the growth of several mammalian cell lines. The nature of the pyrone ring was shown to be important to potency of inhibition, as was the length and nature of substituents in the side chain of the analogues. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.070

文献信息

• PROCESS FOR THE PREPARATION OF SUBSTITUTED PYRIDONE CARBOXYLIC ACIDS
  申请人：KULANGARA VIJAYA RAJ KUNIYIL

  公开号：US20100076199A1

  公开（公告）日：2010-03-25

  The present invention relates to methods for the preparation of pyridone carboxylic acids for use as intermediates in the preparation of various synthetic organic compounds. The pyridone carboxylic acids can for example be used as intermediates in the production of potent antitumor agents, antifungal agents, antiviral agents, psychotherapeutic agents or contrast imaging agents for MRI.

  本发明涉及用于制备吡啶酮羧酸的方法，用作合成各种有机化合物时的中间体。吡啶酮羧酸可以作为强效抗肿瘤药物、抗真菌药物、抗病毒药物、心理治疗药物或MRI对比成像剂的中间体。
• The Acid-catalyzed Reaction of the 2-Oxabicyclo[4.1.0]hept-3-en-5-one System: Isomerization from Homo-4-pyrones into 2-Furylacetone Derivatives
  作者：Hiroshi Yamaoka、Ikuhiro Mishima、Mitsuko Miyamoto、Terukiyo Hanafusa

  DOI：10.1246/bcsj.53.469

  日期：1980.2

  monocyclopropanation of 4-pyrones with dimethyloxosulfonium methylide, using a dimethyl sulfoxide hexamethylphosphoric triamide medium in place of neat dimethyl sulfoxide, gave homo-4-pyrone derivatives, which were then rearranged into the 2-furylacetone derivatives, along with hydra ted triketones or the dehydrated naphtho[2,1-b]furan derivative, by means of strong acid catalysis at room temperature.

  4-吡喃酮与二甲基氧锍的单环丙烷化反应，使用二甲基亚砜六甲基磷三酰胺介质代替纯二甲基亚砜，得到均-4-吡喃酮衍生物，然后将其重排为 2-呋喃基丙酮衍生物，以及水合三酮或在室温下通过强酸催化制备脱水萘并[2,1-b]呋喃衍生物。
• Intramolecular carboxylic acid trapping of pyran-4-one derived zwitterions: A novel synthesis of fused bicyclic lactones
  作者：F.G. West、C.M. Amann、P.V. Fisher

  DOI：10.1016/0040-4039(94)88351-3

  日期：1994.12

  Pyran-4-ones bearing carboxylic acid side chains were prepared either by direct carboxylation with carbon dioxide or through oxidative cleavage of side chain olefins. Irradiation in a non-nucleophilic solvent yielded fused bicyclic lactones. The efficiency of the reaction was not dependent on ring substitution.

  带有羧酸侧链的吡喃-4-酮可通过用二氧化碳直接羧化或通过侧链烯烃的氧化裂解来制备。在非亲核溶剂中辐照产生稠合的双环内酯。反应的效率不取决于环取代。
• Photoisomerization of 4-hydroxypyrylium cations in concentrated sulfuric acid
  作者：James W. Pavlik、Arthur D. Patten、David R. Bolin、Kenneth C. Bradford、Edward L. Clennan

  DOI：10.1021/jo00197a040

  日期：1984.11
• Intramolecular alkene trapping of pyran-4-one-derived Zwitterions: a novel synthesis of diquinanes and hydrindans
  作者：F. G. West、Peter V. Fisher、Atta M. Arif

  DOI：10.1021/ja00057a066

  日期：1993.2