5-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one | 1017279-51-4

• 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-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one
• 英文别名: 2-(Oxan-2-yloxymethyl)-5-prop-2-ynoxypyran-4-one
• CAS: 1017279-51-4
• 化学式: C₁₄H₁₆O₅
• 分子量: 264.278
• InChiKey: KMEQCZVGAJNVLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one 、 甲胺 以 乙醇 、 水 为溶剂， 反应 3.0h， 以94%的产率得到1-methyl-5-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-1H-pyridin-4-one
  参考文献：
  名称：

  Modular Synthesis of Candidate Indole-based Insulin Mimics by Claisen Rearrangement

  摘要：

  A modular synthetic route to (indolyl)kojic acid anti-diabetes agents has been developed. Sonogashira coupling of a protected iodoaniline with a propargyl kojate was used to construct an (indole)methyl kojate. Its heteroaromatic Claisen rearrangement, followed by tautomerization to return the indole and pyrone rings, was used to create the biaryl C-C bond. This route should enable collections of insulin mimic drug candidates to be prepared from a few basic building blocks.

  DOI：

  10.1021/ol800058d
• 作为产物：
  描述：

  3-溴丙炔 、 5-hydroxy-2-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-4H-pyran-4-one 在 四丁基溴化铵 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 12.0h， 以99%的产率得到5-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one
  参考文献：
  名称：

  Modular Synthesis of Candidate Indole-based Insulin Mimics by Claisen Rearrangement

  摘要：

  A modular synthetic route to (indolyl)kojic acid anti-diabetes agents has been developed. Sonogashira coupling of a protected iodoaniline with a propargyl kojate was used to construct an (indole)methyl kojate. Its heteroaromatic Claisen rearrangement, followed by tautomerization to return the indole and pyrone rings, was used to create the biaryl C-C bond. This route should enable collections of insulin mimic drug candidates to be prepared from a few basic building blocks.

  DOI：

  10.1021/ol800058d

文献信息

• Modular Synthesis of Candidate Indole-based Insulin Mimics by Claisen Rearrangement
  作者：Xin Xiong、Michael C. Pirrung

  DOI：10.1021/ol800058d

  日期：2008.3.1

  A modular synthetic route to (indolyl)kojic acid anti-diabetes agents has been developed. Sonogashira coupling of a protected iodoaniline with a propargyl kojate was used to construct an (indole)methyl kojate. Its heteroaromatic Claisen rearrangement, followed by tautomerization to return the indole and pyrone rings, was used to create the biaryl C-C bond. This route should enable collections of insulin mimic drug candidates to be prepared from a few basic building blocks.