4,4a,5,6,7,8-hexahydro-8-hydroxy-4a,5-dimethylnaphthalen-2(3H)-one | 76015-87-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,4a,5,6,7,8-hexahydro-8-hydroxy-4a,5-dimethylnaphthalen-2(3H)-one
• 英文别名: (4aR,5S,8R)-8-hydroxy-4a,5-dimethyl-3,4,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 76015-87-7；76015-88-8；122872-02-0
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: LLXGJLLSVBRJSE-XXILOJSOSA-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：

  4,4a,5,6,7,8-hexahydro-8-hydroxy-4a,5-dimethylnaphthalen-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 (1R,4S,4aR,6R)-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：

  4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-1-phenylthionaphthalen-2(3H)-one 在 二乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 42.33h， 生成 4,4a,5,6,7,8-hexahydro-8-hydroxy-4a,5-dimethylnaphthalen-2(3H)-one
  参考文献：
  名称：

  Hagiwara, Hisahiro; Uda, Hisashi; Kodama, Tsutomu, Journal of the Chemical Society. Perkin transactions I, 1980, p. 963 - 977

  摘要：

  DOI：

文献信息

• Total synthesis of five natural eremophilane-type sesquiterpenoids
  作者：Zhe Meng、Bo Liu

  DOI：10.1039/c7ob02769a

  日期：——

  The first total syntheses of five natural eremophilane-type sesquiterpenoids were achieved in 4–12 steps via a common synthetic intermediate. The syntheses feature a double Michael addition, Robinson annulation, α-enolization of an unsaturated ketone, and Pd-catalyzed Suzuki coupling reaction to install the side chain. This synthetic strategy could be easily extended to other eremophilane-type sesquiterpenoids

  通过一个普通的合成中间体，在4至12个步骤中完成了5种天然艾草双酚倍半萜类化合物的第一个总合成。合成具有双迈克尔加成反应，罗宾逊环化，不饱和酮的α-烯丙基化和Pd催化的Suzuki偶联反应以安装侧链。这种合成策略可以很容易地扩展到其他具有类似双环骨架的天青石型倍半萜。
• 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.