ethyl 5-bromo-2'-(dimethylamino)-3-oxo-3H-spiro[benzofuran-2,3'-chroman]-6'-carboxylate | 1357090-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ethyl 5-bromo-2'-(dimethylamino)-3-oxo-3H-spiro[benzofuran-2,3'-chroman]-6'-carboxylate
• CAS: 1357090-52-8
• 化学式: C₂₁H₂₀BrNO₅
• 分子量: 446.298
• InChiKey: MXTHHOACLWKFRH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-bromo-2'-(dimethylamino)-3-oxo-3H-spiro[benzofuran-2,3'-chroman]-6'-carboxylate 在 silica gel 作用下， 以 Petroleum ether 为溶剂， 生成 ethyl 3-((5-bromo-3-oxo-2,3-dihydrobenzofuran-2-yl)methyl)-4-hydroxybenzoate
  参考文献：
  名称：

  Construction of Aromatic [5,5] Spiroketals via Hypoiodite-Catalyzed Etherification Combined in Relay Cascades

  摘要：

  An approach is developed for the synthesis of bisbenzannelated spiro[5,5]ketals via a catalytic relay reaction cascade involving a new cycloetherification, which is prompted by fluoride and catalyzed by the hypoiodite species generated in situ from irradiative aerobic oxidation of an iodide ion formed in the former step of the reaction cascade.

  DOI：

  10.1021/ol300107v
• 作为产物：
  描述：

  (E)-2-dimethylaminomethylene-5-bromo-3(2H)-benzofuranone 、 ethyl 4-((tert-butyldimethylsilyl)oxy)-3-(iodomethyl)benzoate 在 四丁基氟化铵 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到ethyl 5-bromo-2'-(dimethylamino)-3-oxo-3H-spiro[benzofuran-2,3'-chroman]-6'-carboxylate
  参考文献：
  名称：

  Construction of Aromatic [5,5] Spiroketals via Hypoiodite-Catalyzed Etherification Combined in Relay Cascades

  摘要：

  An approach is developed for the synthesis of bisbenzannelated spiro[5,5]ketals via a catalytic relay reaction cascade involving a new cycloetherification, which is prompted by fluoride and catalyzed by the hypoiodite species generated in situ from irradiative aerobic oxidation of an iodide ion formed in the former step of the reaction cascade.

  DOI：

  10.1021/ol300107v