2-(5-chloro-2-methyl-1H-indol-3-yl)-3-hydroxy-6-hydroxymethylpyran-4-one | 1017279-77-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(5-chloro-2-methyl-1H-indol-3-yl)-3-hydroxy-6-hydroxymethylpyran-4-one
• CAS: 1017279-77-4
• 化学式: C₁₅H₁₂ClNO₄
• 分子量: 305.718
• InChiKey: VMNIAWPKEOKFGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.95
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  86.46
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  tert-butyl 5-chloro-2-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3- yloxymethyl]indole-1-carboxylate 以73%的产率得到2-(5-chloro-2-methyl-1H-indol-3-yl)-3-hydroxy-6-hydroxymethylpyran-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