5-carboethoxy-4-hydroxy-6-methyl-2H-pyran-2-one | 66533-46-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 5-carboethoxy-4-hydroxy-6-methyl-2H-pyran-2-one
• 英文别名: ethyl 4-hydroxy-6-methyl-2-oxo-2H-pyran-5-carboxylate；5-ethoxycarbonyl-4-hydroxy-6-methyl-2-pyrone；2H-Pyran-5-carboxylic acid, 4-hydroxy-6-methyl-2-oxo-, ethyl ester；ethyl 4-hydroxy-2-methyl-6-oxopyran-3-carboxylate
• CAS: 66533-46-8
• 化学式: C₉H₁₀O₅
• 分子量: 198.175
• InChiKey: MNIVBCIIYSVEDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 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：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-carboethoxy-4-hydroxy-6-methyl-2H-pyran-2-one 在 偶氮二异丁腈 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 四氯化碳 、 丙酮 为溶剂， 生成 6-bromomethyl-5-ethoxycarbonyl-4-methoxy-6-methyl-2-pyrone
  参考文献：
  名称：

  合成3-酰基四丁酸的新型吡喃酮策略

  摘要：

  通过将5-乙氧基羰基-4-甲氧基-6-甲基-2-吡喃酮转化为3-乙酰基四酸，已证明了吡喃酮作为3-酰基四酸的前体的潜力。

  DOI：

  10.1016/s0040-4039(00)99205-0
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 丙二酰氯 反应 0.33h， 以2.23 g的产率得到5-carboethoxy-4-hydroxy-6-methyl-2H-pyran-2-one
  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

• A new pyrone strategy for the synthesis of 3-acyltetramic acids
  作者：Raymond C.F. Jones、Jacqueline M. Patience

  DOI：10.1016/s0040-4039(00)99205-0

  日期：——

  The potential of pyrones as precursors to 3-acyltetramic acids has been demonstrated by the conversion of 5-ethoxycarbonyl-4-methoxy-6-methyl-2-pyrone into a 3-acetyltetramic acid.

  通过将5-乙氧基羰基-4-甲氧基-6-甲基-2-吡喃酮转化为3-乙酰基四酸，已证明了吡喃酮作为3-酰基四酸的前体的潜力。
• Sakurai, Ikuo; Miyajima, Hisae; Akiyama, Katsuyoshi, Chemical and pharmaceutical bulletin, 1988, vol. 36, p. 2003 - 2011
  作者：Sakurai, Ikuo、Miyajima, Hisae、Akiyama, Katsuyoshi、Shimizu, Sakae、Yamamoto, Yuzuru

  DOI：——

  日期：——
• 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.
• Total Synthesis of Islandic Acid I Methyl Ester, Rosellisin and Rosellisin Aldehyde
  作者：Takeshi Shimizu、Sayoko Hiranuma、Tsumoru Watanabe、Masayuki Kirihara

  DOI：10.3987/com-93-6568

  日期：——

  Total synthesis of islandic acid I methyl ester (2), rosellisin (3) and rosellisin aldehyde (4) has been accomplished starting from 4-hydroxy-5-hydroxymethyl-6-methyl-2H-pyran-2-one (9a) via formylation of 9a with dichloromethyl methyl ether and titanium tetrachloride as a key step.
• JONES, RAYMOND C. F.;PATIENCE, JACQUELINE M., TETRAHEDRON LETT., 30,(1989) N4, C. 3217-3218
  作者：JONES, RAYMOND C. F.、PATIENCE, JACQUELINE M.

  DOI：——

  日期：——