ethyl (E)-5-(4-methoxyphenoxy)pent-2-enoate | 1374019-06-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: ethyl (E)-5-(4-methoxyphenoxy)pent-2-enoate
• CAS: 1374019-06-3
• 化学式: C₁₄H₁₈O₄
• 分子量: 250.295
• InChiKey: XPFBSPCDBJWMIP-GQCTYLIASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  18.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl (E)-5-(4-methoxyphenoxy)pent-2-enoate 在 水 、 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 19.0h， 以2.23 g的产率得到(E)-5-(4-methoxyphenoxy)pent-2-enoic acid
  参考文献：
  名称：

  Total Synthesis of Mevashuntin

  摘要：

  The total synthesis of (+/-)-mevashuntin, a structurally unique naturally occurring pyrano-naphthoquinone-thiazolone, is described. The route is centered upon a late stage regioselective Diels-Alder reaction between two highly functionalized components, as well as an improved protocol for the one pot synthesis of benzothiazolones from ortho-bromoaryl isothiocyanates. The strategy results in a highly convergent route, providing access to the natural product in 11 steps from 3-(4-methoxyphenoxy)propanol and confirming its relative stereochemistry.

  DOI：

  10.1021/ol300221e
• 作为产物：
  描述：

  4-甲氧基苯酚 在 manganese(IV) oxide 、 potassium carbonate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 ethyl (E)-5-(4-methoxyphenoxy)pent-2-enoate
  参考文献：
  名称：

  Total Synthesis of Mevashuntin

  摘要：

  The total synthesis of (+/-)-mevashuntin, a structurally unique naturally occurring pyrano-naphthoquinone-thiazolone, is described. The route is centered upon a late stage regioselective Diels-Alder reaction between two highly functionalized components, as well as an improved protocol for the one pot synthesis of benzothiazolones from ortho-bromoaryl isothiocyanates. The strategy results in a highly convergent route, providing access to the natural product in 11 steps from 3-(4-methoxyphenoxy)propanol and confirming its relative stereochemistry.

  DOI：

  10.1021/ol300221e