4-tert-butyl 1-ethyl 2-hydroxy-3-methylenesuccinate | 1447736-34-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 4-tert-butyl 1-ethyl 2-hydroxy-3-methylenesuccinate
• 英文别名: 4-O-tert-butyl 1-O-ethyl 2-hydroxy-3-methylidenebutanedioate
• CAS: 1447736-34-6
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: RVNHIASSAMYCRE-UHFFFAOYSA-N

物化性质

• 沸点：
  316.0±37.0 °C(Predicted)
• 密度：
  1.097±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-tert-butyl 1-ethyl 2-hydroxy-3-methylenesuccinate 在 三溴化磷 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以69%的产率得到4-tert-butyl 1-ethyl 3-(bromomethyl)but-2-enedioate
  参考文献：
  名称：

  Enynone dihydroxylation–cyclisation as a route to densely functionalised 3(2H)-furanone derivatives: an approach to the core of the zaragozic acids

  摘要：

  The synthesis of an advanced intermediate is described that could secure the polyoxygenated core of zaragozic acids and related natural products. The key strategy employs a two-step synthesis of the 3(2H)-furanone ring system by catalytic dihydroxylation-mercury(II)/acid-catalysed cyclisation with concomitant deprotection. The scope of the 3(2H)-furanone synthesis has been evaluated, and this ring system is shown to remain intact in multi-step reaction sequences. Access to novel, highly oxygenated 3(2H)-furanone derivatives has been achieved. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.125
• 作为产物：
  描述：

  乙醛酸乙酯 、 丙烯酸叔丁酯 在 三乙烯二胺 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 48.0h， 以58%的产率得到4-tert-butyl 1-ethyl 2-hydroxy-3-methylenesuccinate
  参考文献：
  名称：

  Enynone dihydroxylation–cyclisation as a route to densely functionalised 3(2H)-furanone derivatives: an approach to the core of the zaragozic acids

  摘要：

  The synthesis of an advanced intermediate is described that could secure the polyoxygenated core of zaragozic acids and related natural products. The key strategy employs a two-step synthesis of the 3(2H)-furanone ring system by catalytic dihydroxylation-mercury(II)/acid-catalysed cyclisation with concomitant deprotection. The scope of the 3(2H)-furanone synthesis has been evaluated, and this ring system is shown to remain intact in multi-step reaction sequences. Access to novel, highly oxygenated 3(2H)-furanone derivatives has been achieved. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2013.05.125