(4aS,5R,8S)-8-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one | 852384-69-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,5R,8S)-8-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
• 英文别名: (4aS,5R,8S)-8-hydroxy-4a,5-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 852384-69-1
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: LLXGJLLSVBRJSE-ZHAHWJHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (4aS,5R,8S)-8-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 在 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 87.83h， 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：

  2,3-Dimethyl-2-(3-oxobutyl)cyclohexanone 在 sodium methylate 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 (4aS,5R,8S)-8-hydroxy-4a,5-dimethyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
  参考文献：
  名称：

  环氧eujindole A的全合成

  摘要：

  首次完成了从 Eupenicillium javanicum 中分离出的结构不寻常的吲哚二萜环氧eujindole A的全合成。该合成采用后期阳离子环化策略，该策略利用了富含电子的烯烃底物。CDE 环系统通过对映选择性共轭加成/烷基化、Luche 环化和 Nozaki-Hiyama-Kishi 反应组装。重度取代的 A 环通过 Suzuki-Miyaura 偶联和阳离子环化构建，桥连的稠合 B 环通过 Prins 反应形成。

  DOI：

  10.1021/jacs.5b09198

文献信息

• Total Syntheses of Anominine and Tubingensin A
  作者：Ming Bian、Zhen Wang、Xiaochun Xiong、Yu Sun、Carlo Matera、K. C. Nicolaou、Ang Li

  DOI：10.1021/ja302765m

  日期：2012.5.16

  A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6 pi-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.