tert-butyl 2-[1-methyl-4-oxo-6-(tetrahydropyran-2-yloxymethyl)-1,4-dihydropyridin-3-yloxymethyl]-indole-1-carboxylate | 1017279-95-6

• 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: tert-butyl 2-[1-methyl-4-oxo-6-(tetrahydropyran-2-yloxymethyl)-1,4-dihydropyridin-3-yloxymethyl]-indole-1-carboxylate
• CAS: 1017279-95-6
• 化学式: C₂₆H₃₂N₂O₆
• 分子量: 468.55
• InChiKey: UVVSYMNOAGBHTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.75
• 重原子数：
  34.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  80.92
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[1-methyl-4-oxo-6-(tetrahydropyran-2-yloxymethyl)-1,4-dihydropyridin-3-yloxymethyl]-indole-1-carboxylate 反应 72.0h， 以53%的产率得到3-hydroxy-6-hydroxymethyl-1-methyl-2-(2-methyl-1H-indol-3-yl)-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：

  1-methyl-5-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-1H-pyridin-4-one 、 N-Boc-2-碘苯胺 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 四丁基氟化铵 作用下， 以 苯 、 四氢呋喃 为溶剂， 反应 13.0h， 以68%的产率得到tert-butyl 2-[1-methyl-4-oxo-6-(tetrahydropyran-2-yloxymethyl)-1,4-dihydropyridin-3-yloxymethyl]-indole-1-carboxylate
  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