(1'R,4'S,4'aS,6'S,7'R,8'aR)-7'-allyl-4'a-hydroxymethyl-1',4',8'a-trihydro-(1',4'-methanonaphtho-6',7'-epoxy)-5',8'-dione | 1360808-55-4

• 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-4'a-hydroxymethyl-1',4',8'a-trihydro-(1',4'-methanonaphtho-6',7'-epoxy)-5',8'-dione
• 英文别名: (1R,2S,4S,6R,8R,9S)-2-(hydroxymethyl)-6-prop-2-enyl-5-oxatetracyclo[7.2.1.02,8.04,6]dodec-10-ene-3,7-dione
• CAS: 1360808-55-4
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: LJYXCHUXPAXTOR-NRVHSXBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  66.9
• 氢给体数：
  1
• 氢受体数：
  4

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-4'a-hydroxymethyl-1',4',8'a-trihydro-(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 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 3.5h， 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：

  (1R,2S,7R,8S)-4-prop-2-enyltricyclo[6.2.1.02,7]undeca-4,9-diene-3,6-dione 在 双氧水 、 sodium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 1.92h， 生成 (1'R,4'S,4'aS,6'S,7'R,8'aR)-7'-allyl-4'a-hydroxymethyl-1',4',8'a-trihydro-(1',4'-methanonaphtho-6',7'-epoxy)-5',8'-dione
  参考文献：
  名称：

  新型生物活性环氧醌二聚体（+/-）-torreyanic acid的全合成：仿生方法。

  摘要：

  [反应：见正文]可以容易地完成由七个环组成并带有致密的，杂色的氧官能化的，复杂的，具有生物活性的二聚天然产物（+/-）-torreyanic酸的全合成。烯丙基取代的对苯醌8.我们的合成策略包括制作环氧醌单体，用于仿生级联工艺，包括串联6pi电环化和Diels-Alder二聚化。

  DOI：

  10.1021/ol0483551

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.
• Total Synthesis of the Novel, Biologically Active Epoxyquinone Dimer (±)-Torreyanic Acid:  A Biomimetic Approach
  作者：Goverdhan Mehta、Subhas Chandra Pan

  DOI：10.1021/ol0483551

  日期：2004.10.1

  [reaction: see text] A total synthesis of the complex, biologically active, dimeric natural product (+/-)-torreyanic acid, which is composed of seven rings and laced with dense, variegated oxy-functionalization, has been accomplished from readily available allyl-substituted p-benzoquinone 8. Our synthetic stratagem involves crafting an epoxyquinone monomer for use in a biomimetic cascade process involving

  [反应：见正文]可以容易地完成由七个环组成并带有致密的，杂色的氧官能化的，复杂的，具有生物活性的二聚天然产物（+/-）-torreyanic酸的全合成。烯丙基取代的对苯醌8.我们的合成策略包括制作环氧醌单体，用于仿生级联工艺，包括串联6pi电环化和Diels-Alder二聚化。