methyl <5-(allyloxy)-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate | 144108-02-1

• 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: methyl <5-(allyloxy)-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate
• 英文别名: Methyl 2-hydroxy-6-(2-methoxy-2-oxoethyl)-4-prop-2-enoxybenzoate
• CAS: 144108-02-1
• 化学式: C₁₄H₁₆O₆
• 分子量: 280.277
• InChiKey: IJWBUAYRDMRRAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl <5-(allyloxy)-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 lithium chloride 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 27.0h， 生成 methyl 4-(allyloxy)-6-<(5'S,6'R,7'S,8'R)-6'-<(tert-butyldimethylsilyl)oxy>-7',8'-(cyclohexylidenedioxy)-5'-methoxy-2'-oxonon-3'(E)-enyl>-2-hydroxybenzoate
  参考文献：
  名称：

  An improved synthesis of naphthoate precursors to olivin

  摘要：

  An improved synthesis of olivin synthetic intermediate 3 is described. The synthesis involves the Homer-Wadsworth-Emmons coupling of 14 and 16, the diastereoselective vinylcuprate addition to enone 20, and the condensation of isocoumarin 25 and methyl acetate. A parallel sequence starting from allyl ether 26 has provided naphthoate 35 that is suitably differentiated for glycosylation studies.

  DOI：

  10.1021/jo00050a047
• 作为产物：
  描述：

  dimethyl 3,5-dihydroxyhomophthalate 、 3-溴丙烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以85%的产率得到methyl <5-(allyloxy)-3-hydroxy-2-(methoxycarbonyl)phenyl>acetate
  参考文献：
  名称：

  An improved synthesis of naphthoate precursors to olivin

  摘要：

  An improved synthesis of olivin synthetic intermediate 3 is described. The synthesis involves the Homer-Wadsworth-Emmons coupling of 14 and 16, the diastereoselective vinylcuprate addition to enone 20, and the condensation of isocoumarin 25 and methyl acetate. A parallel sequence starting from allyl ether 26 has provided naphthoate 35 that is suitably differentiated for glycosylation studies.

  DOI：

  10.1021/jo00050a047

文献信息

• An improved synthesis of naphthoate precursors to olivin
  作者：William R. Roush、Megan Murphy

  DOI：10.1021/jo00050a047

  日期：1992.11

  An improved synthesis of olivin synthetic intermediate 3 is described. The synthesis involves the Homer-Wadsworth-Emmons coupling of 14 and 16, the diastereoselective vinylcuprate addition to enone 20, and the condensation of isocoumarin 25 and methyl acetate. A parallel sequence starting from allyl ether 26 has provided naphthoate 35 that is suitably differentiated for glycosylation studies.