tert-butyl (2-{3-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxy]prop-1-ynyl}phenyl)carbamate | 1017279-56-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: tert-butyl (2-{3-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxy]prop-1-ynyl}phenyl)carbamate
• CAS: 1017279-56-9
• 化学式: C₂₅H₂₉NO₇
• 分子量: 455.508
• InChiKey: LIZXKTBKROWUEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.46
• 重原子数：
  33.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  96.23
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  5-prop-2-ynyloxy-2-(tetrahydropyran-2-yloxymethyl)-pyran-4-one 、 N-Boc-2-碘苯胺 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62%的产率得到tert-butyl (2-{3-[4-oxo-6-(tetrahydropyran-2-yloxymethyl)-4H-pyran-3-yloxy]prop-1-ynyl}phenyl)carbamate
  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