(1'S,4'R,4'aS,5'R,6'S,7'R,8'aS)-7'-allyl-8'a-bromo-5'-hydroxy-4'a-hydroxymethyl-1',4'-dihydro-(1',4'-methanonaphtho-6',7'-epoxy)-8'-one | 1360808-92-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (1'S,4'R,4'aS,5'R,6'S,7'R,8'aS)-7'-allyl-8'a-bromo-5'-hydroxy-4'a-hydroxymethyl-1',4'-dihydro-(1',4'-methanonaphtho-6',7'-epoxy)-8'-one
• CAS: 1360808-92-9
• 化学式: C₁₅H₁₇BrO₄
• 分子量: 341.202
• InChiKey: JZRXBFDRUVFVSR-MZYZVZIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.96
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  70.06
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (1'R,4'S,4'aS,5'R,6'S,7'R,8'aR)-7'-allyl-5'-hydroxy-4'a-hydroxymethyl-1',4',8'a-trihydro-(1',4'-methanonaphtho-6',7'-epoxy)-8'-one 在 1,2-二溴四氯乙烷 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以90%的产率得到(1'S,4'R,4'aS,5'R,6'S,7'R,8'aS)-7'-allyl-8'a-bromo-5'-hydroxy-4'a-hydroxymethyl-1',4'-dihydro-(1',4'-methanonaphtho-6',7'-epoxy)-8'-one
  参考文献：
  名称：

  Total Synthsis of (+)-Ambuic Acid: α-Bromination with 1,2-Dibromotetrachloroethane

  摘要：

  Total synthesis of (+)-ambuic acid has been accomplished from the readily available stereocontrolled Diels-Alder adduct of cyclopentadiene and iodo-1,4-benzoquinone monoketal through an efficient series of steps. A new method for the highly commendable synthesis of alpha-brominated Diels-Alder adduct is described.

  DOI：

  10.1021/jo202357s