(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 | 1360808-62-3

• 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-5'-((spiro-1,3-dioxolane)-1',4'-methanonaphthalene)-8'-one
• CAS: 1360808-62-3
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: USLGJAJMBBGILP-WVWOOGAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

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-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
• 作为产物：
  描述：

  环戊二烯 在 四(三苯基膦)钯 、 CHF₃O₃S*C₂₄H₂₄BNO 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (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
  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