5-(1-methanesulfonyl-1H-indol-2-ylmethoxy)-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one | 1017279-52-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 5-(1-methanesulfonyl-1H-indol-2-ylmethoxy)-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one
• CAS: 1017279-52-5
• 化学式: C₂₁H₂₃NO₇S
• 分子量: 433.482
• InChiKey: IGQLJLQANIZGGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  96.97
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  5-(1-methanesulfonyl-1H-indol-2-ylmethoxy)-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one 以 甲苯 为溶剂， 反应 0.5h， 以45%的产率得到3-hydroxy-2-(1-methanesulfonyl-2-methyl-1H-indol-3-yl)-6-(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
• 作为产物：
  描述：

  5-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one 、 甲磺酰胺,N-(2-碘苯基)- 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 苯 为溶剂， 反应 12.0h， 以70%的产率得到5-(1-methanesulfonyl-1H-indol-2-ylmethoxy)-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