(4aR,5S,8R)-8-(t-butyldimethylsilyloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one | 852384-60-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aR,5S,8R)-8-(t-butyldimethylsilyloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• 英文别名: (4aR,5S,8R)-8-[tert-butyl(dimethyl)silyl]oxy-4a,5-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 852384-60-2
• 化学式: C₁₈H₃₂O₂Si
• 分子量: 308.536
• InChiKey: ZUZPVJFCPQKPOQ-FDQGKXFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4aR,5S,8R)-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 (3R,4aR,5S,8R)-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
• 作为产物：
  描述：

  (rel-4aS,5R)-4a,5-dimethyl-4,4a5,6,7,8-hexahydronaphthalen-2(3H)-one 在 咪唑 、 甲醇 、 lithium hydroxide 、 Oxone 、 碳酸氢钠 、 对甲苯磺酸 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 74.5h， 生成 (4aR,5S,8R)-8-(t-butyldimethylsilyloxy)-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

文献信息

• Enantioselective Syntheses of (+)-Xylarenal A and <i>e</i><i>nt</i>-Xylarenal A
  作者：Sandra Díaz、Asensio González、Ben Bradshaw、Javier Cuesta、Josep Bonjoch

  DOI：10.1021/jo0502450

  日期：2005.4.1

  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.