methyl 4-methoxy-6-methyl-2-oxo-2H-pyran-5-carboxylate | 668-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: methyl 4-methoxy-6-methyl-2-oxo-2H-pyran-5-carboxylate
• 英文别名: 4-methoxy-5-methoxycarbonyl-6-methyl-2-pyrone；2H-Pyran-5-carboxylic acid, 4-methoxy-6-methyl-2-oxo-, methyl ester；methyl 4-methoxy-2-methyl-6-oxopyran-3-carboxylate
• CAS: 668-40-6
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: FTRWTXSSRMFVQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 4-methoxy-6-methyl-2-oxo-2H-pyran-5-carboxylate 在 dipotassium hydrogenphosphate 、 sodium dihydrogenphosphate 作用下， 以 乙醇 、 水 为溶剂， 反应 480.0h， 以59%的产率得到2-Methoxy-6-methyl-terephthalic acid 1-methyl ester
  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：

  dipyrone methyl ether 以 sodium hydroxide 、 乙醚 为溶剂， 反应 0.42h， 生成 methyl 4-methoxy-6-methyl-2-oxo-2H-pyran-5-carboxylate
  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：

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。
• Total Syntheses of Daldiniapyrone, Annularin B, and (±)-Annularin F
  作者：Richard Hsung、Aleksey Kurdyumov、R. Muñoz

  DOI：10.1055/s-2006-942355

  日期：2006.6

  The first concise total syntheses of daldiniapyrone, annularin B, and (±)-annularin F are described.

  本文首次对达迪尼亚酮、环烯醚萜醇 B 和环烯醚萜醇 F 进行了简要的全面综述。
• 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.