4-tert-butyl 1-ethyl 3-(bromomethyl)but-2-enedioate | 1447736-35-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-tert-butyl 1-ethyl 3-(bromomethyl)but-2-enedioate
• 英文别名: 1-tert-butyl 4-ethyl 2-(bromomethyl)but-2-enedioate；1-O-tert-butyl 4-O-ethyl 2-(bromomethyl)but-2-enedioate
• CAS: 1447736-35-7
• 化学式: C₁₁H₁₇BrO₄
• 分子量: 293.158
• InChiKey: YWYAIKRQPNOKLZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-tert-butyl 1-ethyl 3-(bromomethyl)but-2-enedioate 、 苯甲醇 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.17h， 以59%的产率得到4-tert-butyl 1-ethyl 2-benzyloxy-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
• 作为产物：
  描述：

  丙烯酸叔丁酯 在 三乙烯二胺 、 三溴化磷 作用下， 以 1,4-二氧六环 、 乙醚 、 甲苯 为溶剂， 反应 49.0h， 生成 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