(1'R,4'S,4'aS,8'aR)-7'-allyl-1',4',4'a,8'a-tetrahydro-(1',4'-methanonaphthalene)-5',8'-dione | 1360808-57-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1'R,4'S,4'aS,8'aR)-7'-allyl-1',4',4'a,8'a-tetrahydro-(1',4'-methanonaphthalene)-5',8'-dione
• 英文别名: (1S,2R,7S,8R)-4-prop-2-enyltricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione
• CAS: 1360808-57-6
• 化学式: C₁₄H₁₄O₂
• 分子量: 214.264
• InChiKey: XWNRTSJYUJVGBD-HIAZDOBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1'R,4'S,4'aS,8'aR)-7'-allyl-1',4',4'a,8'a-tetrahydro-(1',4'-methanonaphthalene)-5',8'-dione 在 双氧水 、 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以745 mg的产率得到(1'R,4'S,4'aS,6'S,7'R,8'aR)-7'-allyl-1',4',4'a,8'a-tetrahydro-(1',4'-methanonaphtho-6',7'-epoxy)-5',8'-dione
  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
• 作为产物：
  描述：

  (1'R,4'S,4'aS,8'aR)-7'-allyl-1',4',4'a,8'a-tetrahydro-5'-((spiro-1,3-dioxolane)-1',4'-methanonaphthalene)-8'-one 在 硫酸 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 0.5h， 生成 (1'R,4'S,4'aS,8'aR)-7'-allyl-1',4',4'a,8'a-tetrahydro-(1',4'-methanonaphthalene)-5',8'-dione
  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

文献信息

• Total Synthsis of (+)-Ambuic Acid: α-Bromination with 1,2-Dibromotetrachloroethane
  作者：Sun Hee Jung、Geum-Sook Hwang、Sung Il Lee、Do Hyun Ryu

  DOI：10.1021/jo202357s

  日期：2012.3.2

  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.