5-乙酰基-4-甲氧基-6-甲基吡喃-2-酮 | 80927-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 5-乙酰基-4-甲氧基-6-甲基吡喃-2-酮
• 英文名称: 5-acetyl-4-methoxy-6-methyl-α-pyrone
• 英文别名: 5-acetyl-4-methoxy-6-methyl-2-pyrone；2H-Pyran-2-one, 5-acetyl-4-methoxy-6-methyl-；5-acetyl-4-methoxy-6-methylpyran-2-one
• CAS: 80927-97-5
• 化学式: C₉H₁₀O₄
• 分子量: 182.176
• InChiKey: HJCDDONWKNVSRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-乙酰基-4-甲氧基-6-甲基吡喃-2-酮 在 dipotassium hydrogenphosphate 、 sodium dihydrogenphosphate 作用下， 以 乙醇 、 水 为溶剂， 反应 480.0h， 以73%的产率得到4-acetyl-3-methoxy-5-methylbenzoic acid
  参考文献：
  名称：

  Sakurai, Ikuo; Miyajima, Hisae; Akiyama, Katsuyoshi, Chemical and pharmaceutical bulletin, 1988, vol. 36, p. 2003 - 2011

  摘要：

  DOI：
• 作为产物：
  描述：

  乙酰丙酮 在 silver(l) oxide 作用下， 以 氯仿 为溶剂， 反应 7.33h， 生成 5-乙酰基-4-甲氧基-6-甲基吡喃-2-酮
  参考文献：
  名称：

  Synthesis of pyrenocines A, B and pyrenochaetic acid A

  摘要：

  DOI：

  10.1016/s0040-4020(01)87700-0

文献信息

• Substrate Diversity of Macrophomate Synthase Catalyzing an Unusual Multistep Transformation from 2-Pyrones to Benzoates
  作者：Kenji WATANABE、Takashi MIE、Akitami ICHIHARA、Hideaki OIKAWA、Mamoru HONMA

  DOI：10.1271/bbb.64.530

  日期：2000.1

  Macrophomate synthase, which we have recently purified, catalyzes an unusual multistep transformation from 5-acetyl-4-methoxy-6-methyl-2-pyrone to 4-acetyl-3-methoxy-5-methyl-benzoic acid (macrophomic acid). To investigate the substrate diversity of the enzyme, 40 analogs of 2-pyrone were prepared and their relative efficiency was examined in the enzymatic conversions. The experimental results reveal the structural requirements of the substrates and the rough size of the enzyme active site, and eliminate the ambiguity caused by contamination by other enzymes in the whole-cell experiments.

  我们最近纯化了一种名为黑腐醇合酶的酶，它催化一种不寻常的多步转化过程，从5-乙酰基-4-甲氧基-6-甲基-2-吡営转变为4-乙酰基-3-甲氧基-5-甲基苯甲酸（黑腐酸）。为了研究该酶的底物多样性，我们制备了40种2-吡喃酮的类似物，并考察了它们在酶促转化中的相对效率。实验结果揭示了底物的结构要求和酶活性位点的大致尺寸，并消除了全细胞实验中因其他酶污染导致的模糊性。
• Trapping and Structural Elucidation of an Intermediate in the Macrophomate Synthase Reaction Pathway
  作者：Jörg M. Serafimov、Thomas Westfeld、Beat H. Meier、Donald Hilvert

  DOI：10.1021/ja073087y

  日期：2007.8.1

  Macrophomate synthase (MPS) catalyzes the reaction of oxaloacetate and 2-pyrones to give, over multiple steps, substituted benzoates. We detected a transient intermediate in the course of this transformation by monitoring the total time course either spectroscopically at 305 nm or by 1H NMR. This species was trapped by quenching the reaction with acetonitrile and cooling the sample to 270 K; its structure

  巨藻酸盐合酶 (MPS) 催化草酰乙酸和 2-吡喃酮的反应，通过多个步骤生成取代的苯甲酸酯。我们通过在 305 nm 光谱或 1 H NMR 上监测总时间过程，在此转化过程中检测到一个瞬态中间体。通过用乙腈淬灭反应并将样品冷却至 270 K 来捕获该物质；通过完整的 2D NMR 光谱分析确定其结构为烯丙基环己二烯醇。它是根据 Michaelis-Menten 动力学以与草酰乙酸脱羧（反应序列的第一步）一样快或更快的速率形成的。MPS 不催化该化合物脱水生成巨藻酸盐，这限制了整个过程的速率。尽管这些结果阐明了 MPS 催化的最后阶段，他们没有阐明早期的 C-C 键形成步骤。因此，将需要其他方法来解决关于这种酶是否...
• Active site mutagenesis of the putative Diels–Alderase macrophomate synthase
  作者：Jörg M. Serafimov、Hans Christian Lehmann、Hideaki Oikawa、Donald Hilvert

  DOI：10.1039/b703177g

  日期：——

  Although the macrophomate synthase active site is rich in potential functional groups, site-directed mutagenesis shows that only three residues are absolutely required for catalysis of oxaloacetate decarboxylation and trapping of the resulting enolate with a 2-pyrone; the other residues that line the binding pocket are surprisingly tolerant to substitution.

  虽然巨噬细胞酸合成酶的活性位点富含潜在的功能基团，但定点突变显示，只有三个残基是催化草酰乙酸脱羧和用 2-吡喃酮捕获所产生的烯醇酮所绝对必需的；而位于结合口袋的其他残基对取代的耐受性令人惊讶。
• Two new metabolites of hybrid strains KO 0201 and 0211 derived from Penicillium citreo-viride B. IFO 6200 and 4692
  作者：Takashi Nakada、Sho Sudo、Seiji Kosemura、Shosuke Yamamura

  DOI：10.1016/s0040-4039(99)01408-2

  日期：1999.9

  Two new metabolites, citreo-γ-pyrone and citreothiopyrane A, with interesting biological activity have been isolated from the mycelia of hybrid strains KO 0201 and 0211 derived from Penicillium citreo-viride B. IFO 6200 and 4692. Their structures have been elucidated based on their spectral data. In addition, their biological properties are also described. The structure of citreothiolactone previously

  从由青霉-青霉素B. IFO 6200和4692衍生的杂种菌株KO 0201和0211的菌丝体中分离了两种具有有趣生物活性的新的代谢物，瓜-γ-吡喃酮和瓜硫代吡喃A。他们的光谱数据。此外，还描述了它们的生物学特性。先前报道的柠硫内酯的结构已被修改。
• Reduction of a-Pyrone Derivatives with Borane-Methyl Sulfide Complex
  作者：Takeshi Shimizu、Sayoko Hiranuma、Tsumoru Watanabe

  DOI：10.3987/com-93-6509

  日期：——

  Selective reduction of the 5-carbomethoxy- and the 5-carbethoxy-4-hydroxy-2H-pyran-2-one derivatives (5a approximately 11, 19) to yield the 5-hydroxymethyl derivatives (12 approximately 18) was accomplished using 1.1 mol equivalent of borane-methyl sulfide complex. Additionally, reduction of the 3-acetyl-4-hydroxy-2H-pyran-2-one derivatives (23, 26 and 29) with borane-methyl sulfide complex afforded the binary condensed pyrone derivatives (25, 28 and 3 1) in good yields.