2-acetoxymethyl-5-methoxy-4H-pyran-4-one | 33777-49-0

• 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-acetoxymethyl-5-methoxy-4H-pyran-4-one
• 英文别名: 2-acetoxymethyl-5-methoxy-pyran-4-one；2-Acetoxymethyl-5-methoxy-pyran-4-on；2-Acetoxymethyl-5-methoxy-4-oxo-4H-pyran
• CAS: 33777-49-0
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: RLPAXTPIJLIUDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.71
• 重原子数：
  14.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.74
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  5-acetoxy-2-acetoxymethyl-4H-pyran-4-one 在 甲醇 、 三氯化铝 、 silver(l) oxide 作用下， 生成 2-acetoxymethyl-5-methoxy-4H-pyran-4-one
  参考文献：
  名称：

  Derivatives of Kojic Acid

  摘要：

  DOI：

  10.1021/ja01175a060

文献信息

• The Issue of Misidentification of Kojic Acid with Flufuran in Aspergillus flavus
  作者：Marina DellaGreca、Gaetano De Tommaso、Maria Michela Salvatore、Rosario Nicoletti、Andrea Becchimanzi、Mauro Iuliano、Anna Andolfi

  DOI：10.3390/molecules24091709

  日期：——

  profile of this strain showed kojic acid to be the dominant product in cultures on Czapek-Dox broth. However, an accurate review of papers documenting secondary metabolite production in A. flavus also showed that an isomer of kojic acid, identified as 5-(hydroxymethyl)-furan-3-carboxylic acid and named flufuran is reported from this species. The spectroscopic data of kojic acid were almost identical to

  在研究蜜蜂衰退的复杂现象的过程中，从工蜂的血腔中分离出了黄曲霉。对该菌株代谢组学特征的观察表明，曲酸是 Czapek-Dox 肉汤培养物中的主要产物。然而，对记录黄曲霉次生代谢物产生的论文的准确回顾也表明，该物种报告了一种曲酸异构体，被鉴定为 5-(羟甲基)-呋喃-3-羧酸，并命名为氟呋喃。曲酸的光谱数据与文献报道的氟呋喃的光谱数据几乎相同。这激发了对商业曲酸和 5-(羟甲基)-呋喃-3-羧酸的比较研究，突出了一些差异，例如两种化合物的 13C-NMR 和 UV 光谱，表明曲酸被错误地识别为5-(羟甲基)-呋喃-3-羧酸过去曾出现过。
• Brown, Journal of the Chemical Society, 1956, p. 2558
  作者：Brown

  DOI：——

  日期：——
• Pyrones: V—The mass spectra and fragmentation mechanisms of some 3(5)-methoxy-4-pyrones
  作者：David L. McGillivray、Gerald A. Poulton

  DOI：10.1002/oms.1210150110

  日期：1980.1

  AbstractThe mass spectra of methyl kojate (2‐hydroxymethyl‐5‐methoxy‐4H‐pyran‐4‐one), two deuterated analogues and 14 related 3(5)‐methoxy‐4‐pyrones have been studied. These compounds fragment according to a common mechanism, initiated by primary rearrangement of the molecular ion(s). Guidelines which indicate the presence of 3(5)‐methoxy‐4‐pyrones and allow structural determinations to be made from their mass spectra are presented. For the majority of substituents studied, the nature of the substituent has no major effect upon the fragmentation pattern; the cyano group does. The hydroxy counterparts of the above compounds are readily converted for analysis by simple methylation.