tert-butyl 2-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxymethyl]indole-1-carboxylate | 1017279-58-1

• 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-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxymethyl]indole-1-carboxylate
• 英文别名: Tert-butyl 2-[[6-(oxan-2-yloxymethyl)-4-oxopyran-3-yl]oxymethyl]indole-1-carboxylate
• CAS: 1017279-58-1
• 化学式: C₂₅H₂₉NO₇
• 分子量: 455.508
• InChiKey: ANYVXCVVOFJOHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxymethyl]indole-1-carboxylate 反应 3.0h， 以95%的产率得到3-hydroxy-2-(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：

  tert-butyl (2-{3-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxy]prop-1-ynyl}phenyl)carbamate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以90%的产率得到tert-butyl 2-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-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

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.