(3S,4aS,5R,8S)-3-allyl-8-(t-butyldimethylsilyloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one | 852384-71-5

• 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-(t-butyldimethylsilyloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• 英文别名: (3S,4aS,5R,8S)-8-[tert-butyl(dimethyl)silyl]oxy-4a,5-dimethyl-3-prop-2-enyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 852384-71-5
• 化学式: C₂₁H₃₆O₂Si
• 分子量: 348.601
• InChiKey: XHOJVUGPTWBVFY-DFPKUZHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  (3S,4aS,5R,8S)-3-allyl-8-(t-butyldimethylsilyloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 在 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 42.0h， 生成 (1S,4R,4aS,6S)-6-allyl-4,4a-dimethyl-7-oxo-1,2,3,4,4a,5,6,7-octahydronaphthalen-1-yl decanoate
  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)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)-naphthalenone 在 咪唑 、 甲醇 、 Oxone 、 碳酸氢钠 、 对甲苯磺酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.33h， 生成 (3S,4aS,5R,8S)-3-allyl-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.