(E)-5-(4-methoxyphenoxy)pent-2-enoic acid | 1374019-07-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-5-(4-methoxyphenoxy)pent-2-enoic acid
• CAS: 1374019-07-4
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: ZYAZCEGLOQWXHT-DUXPYHPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (E)-5-(4-methoxyphenoxy)pent-2-enoic acid 在 甲醇 、 草酰氯 、 magnesium 、 1,2-二溴乙烷 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.5h， 生成 methyl 2-isopentyl-6-(2-(4-methoxyphenoxy)ethyl)-4-oxo-5,6-dihydropyran-3-carboxylate
  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：

  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

文献信息

• Total Synthesis of Mevashuntin
  作者：Christopher C. Nawrat、Christopher J. Moody

  DOI：10.1021/ol300221e

  日期：2012.3.16

  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.