2-甲氧基-3,5,6-三甲基吡喃-4-酮 | 56070-87-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 中文名称: 2-甲氧基-3,5,6-三甲基吡喃-4-酮
• 英文名称: 2-methoxy-3,5,6-trimethyl-4H-pyran-4-one
• 英文别名: 3.5.6-Trimethyl-2-methoxy-4-pyron；2-methoxy-3,5,6-trimethyl-4-pyrone；2-methoxy-3,5,6-trimethyl-pyran-4-one；4H-Pyran-4-one, 2-methoxy-3,5,6-trimethyl-；2-methoxy-3,5,6-trimethylpyran-4-one
• CAS: 56070-87-2
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: QPYLDNSXXUKCRZ-UHFFFAOYSA-N

物化性质

• 熔点：
  65 °C
• 沸点：
  293.1±35.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-甲氧基-3,5,6-三甲基吡喃-4-酮 在 N-氯代丁二酰亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以67%的产率得到2-(Chloromethyl)-6-methoxy-3,5-dimethylpyran-4-one
  参考文献：
  名称：

  The first total synthesis and structural determination of actinopyrone A

  摘要：

  Actinopyrone A (1) has been synthesized by using our developed remote stereoinduction, Kocienski olefination, Horner-Wadsworth-Emmons olefination, and reductive de-conjugation of the vinylpyrone. A concise method of O-methylation to obtain the gamma-pyrone has also been established. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.05.028
• 作为产物：
  描述：

  6-(1-methyl-2-oxopropyl)-2,2,5-trimethyl-4H-1,3-dioxin-4-one 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-甲氧基-3,5,6-三甲基吡喃-4-酮
  参考文献：
  名称：

  Total Synthesis and Biological Evaluation of Verticipyrone and Analogues

  摘要：

  Total synthesis of verticipyrone, a novel NADH-fumarate reductase inhibitor, has been accomplished by a convergent approach using novel "Reverse Julia olefination" method. During total synthetic studies, we also prepared and evaluated several synthetic verticipyrone analogues, some of which exhibited more potent antiparasitic activity than the natural verticipyrone.

  DOI：

  10.1021/ol0626140

文献信息

• Flexible Total Synthesis of (±)-Aureothin, a Potent Antiproliferative Agent
  作者：Matthias Henrot、Alexandre Jean、Philippe A. Peixoto、Jacques Maddaluno、Michaël De Paolis

  DOI：10.1021/acs.joc.6b00878

  日期：2016.6.17

  Amenable to late-stage preparation of analogues, a flexible and convergent total synthesis of (±)-aureothin is presented. The strategy was based on a desymmetrization of α,α′-dimethoxy-γ-pyrone by a process combining 1,4-addition and alkylation of vinylogous enolate to stereoselectively reach the backbone of the target. Palladium-catalyzed cyanation of an elaborated and isomerizable E,Z dienyl motif

  适用于类似物的后期制备，提出了一种灵活且收敛的（±）-金黄色素的全合成方法。该策略基于α，α'-二甲氧基-γ-吡喃酮的不对称化，该过程通过结合1，4-加成和乙烯基烯醇烯酸酯的烷基化以立体选择性地到达靶标主链的过程来实现。精细和可异构化的E，Z二烯基基序的钯催化氰化反应，然后进行Pinner环化，可以构建四氢呋喃基序，而基于后期氧化的第一种方法却不成功。
• A Concise Route to α′-Methoxy-γ-pyrones and Verticipyrone Based Upon the Desymmetrization of α,α′-Dimethoxy-γ-pyrone
  作者：Michaël De Paolis、Helèna Rosso、Matthias Henrot、Cristina Prandi、Florent d'Herouville、Jacques Maddaluno

  DOI：10.1002/chem.201001780

  日期：——

  Two steps is the rule: A concise synthesis of versatile α′‐methoxy‐γ‐pyrones (see scheme) is described that uses an innovative desymmetrization of α,α′‐dimethoxy‐γ‐pyrone, relying upon conjugate addition of nucleophiles. This new strategy is applied to the preparation of α‐methyl‐ and α‐carboxaldehyde‐α′‐methoxy‐γ‐pyrones and to a short synthesis of verticipyrone.

  规则是两个步骤：描述了一种通用的α'-甲氧基-γ-吡喃酮的简明合成方法（参见方案），该方法利用创新的α，α'-二甲氧基-γ-吡喃酮的去对称性，依赖于亲核试剂的共轭加成。该新策略适用于制备α-甲基和α-甲醛，α'-甲氧基-γ-吡喃酮和维替吡酮的短合成。
• Total synthesis and stereochemical determination of yoshinone A
  作者：Seiichi Shinomiya、Arihiro Iwasaki、Osamu Ohno、Kiyotake Suenaga

  DOI：10.1016/j.phytochem.2016.10.005

  日期：2016.12

  and therefore is expected to be a lead compound for obesity drugs. To establish its absolute configuration, and to provide sufficient amounts for further research, the total synthesis of yoshinone A was achieved through synthesis of its two possible diastereomers.

  2014 年，从海洋蓝藻 Leptolyngbya sp. 中分离出含有 γ-吡喃酮的聚酮化合物 yoshinone A。并确定了其结构。Yoshinone A 抑制 3T3-L1 细胞向脂肪细胞的分化，EC50 值为 420 nM，没有任何细胞毒性，因此有望成为肥胖药物的先导化合物。为了确定其绝对构型，并为进一步研究提供足够的数量，yoshinone A 的全合成是通过合成其两种可能的非对映异构体来实现的。
• Synthesis and evaluation of verticipyrone analogues as mitochondrial complex I inhibitors
  作者：Simon J. Leiris、Omar M. Khdour、Zachary J. Segerman、Krystal S. Tsosie、Jean-Charles Chapuis、Sidney M. Hecht

  DOI：10.1016/j.bmc.2010.03.070

  日期：2010.5

  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.
• Carboalumination/Ni-catalyzed couplings. A short synthesis of verticipyrone
  作者：Bruce H. Lipshutz、Benjamin Amorelli

  DOI：10.1016/j.tetlet.2009.02.167

  日期：2009.5

  Verticipyrone (1) has been synthesized in six overall steps from commercially available ethyl-2-methylacetoacetate. This represents the first successful application of a modified Negishi carboalumination nickel-catalyzed cross-coupling reaction to a chloromethylated pyrone. (C) 2009 Elsevier Ltd. All rights reserved.