(3S,4aS,5R,8S)-3-allyl-8-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one | 852384-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4aS,5R,8S)-3-allyl-8-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• 英文别名: (3S,4aS,5R,8S)-8-hydroxy-4a,5-dimethyl-3-prop-2-enyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 852384-72-6
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: NUJJRKZHZRJYCM-MPXAEWJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3S,4aS,5R,8S)-3-allyl-8-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 在 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium periodate 、 四氧化锇 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 反应 46.0h， 生成 (3R,4aS,5R,8S)-8-decanoyloxy-3-[(1-formyl)vinyl]-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
  参考文献：
  名称：

  Enantioselective Syntheses of (+)-Xylarenal A and ent-Xylarenal A

  摘要：

  The total synthesis of the sesquiterpenoid xylarenal A is reported. This first synthetic entry to an eremophilane terpenoid with an exocyclic vinyl aldehyde unit involves the use of the bicyclic enone (+)-3, which after a gamma-oxidation and alpha '-allylation leads to the formation of the ketone (+)-8. After its acylation, an oxidative cleavage of the allyl side chain followed by alpha-methylenation of the resulting aldehyde gives (+)-xylarenal A (1). The synthesis of (-)-xylarenal A from (-)-3 is also reported. Moreover, the first total synthesis of the trinoreremophilane (+)-1 alpha-hydroxyisoondetianone (5) is described.

  DOI：

  10.1021/jo0502450
• 作为产物：
  描述：

  (4aS,5R,8S)-8-(t-butyldimethylsilyloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 在 四丁基氟化铵 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 39.83h， 生成 (3S,4aS,5R,8S)-3-allyl-8-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
  参考文献：
  名称：

  Enantioselective Syntheses of (+)-Xylarenal A and ent-Xylarenal A

  摘要：

  The total synthesis of the sesquiterpenoid xylarenal A is reported. This first synthetic entry to an eremophilane terpenoid with an exocyclic vinyl aldehyde unit involves the use of the bicyclic enone (+)-3, which after a gamma-oxidation and alpha '-allylation leads to the formation of the ketone (+)-8. After its acylation, an oxidative cleavage of the allyl side chain followed by alpha-methylenation of the resulting aldehyde gives (+)-xylarenal A (1). The synthesis of (-)-xylarenal A from (-)-3 is also reported. Moreover, the first total synthesis of the trinoreremophilane (+)-1 alpha-hydroxyisoondetianone (5) is described.

  DOI：

  10.1021/jo0502450