(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 | 1360808-64-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (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
• 英文别名: (1S,2R,4R,6S,8S,9R)-4-prop-2-enyl-5-oxatetracyclo[7.2.1.02,8.04,6]dodec-10-ene-3,7-dione
• CAS: 1360808-64-5
• 化学式: C₁₄H₁₄O₃
• 分子量: 230.263
• InChiKey: OSIJTAPFKAZDFM-SMQNGZJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (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 在 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 (4aS,5S,6S,7aR,8R,11S,111S)-6-allyl-3,3-dimethyl-4a,7a,8,11-hexahydro-(8,11-methanonaphthonaphtho-5,6-epoxy)-[1-d]-[1,3]dioxin-7(1H)-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
• 作为产物：
  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

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.