Acetic acid (3R,4aS,8aS)-3-isopropyl-8a-methyl-5-oxo-octahydro-naphthalen-4a-yl ester | 144127-02-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Acetic acid (3R,4aS,8aS)-3-isopropyl-8a-methyl-5-oxo-octahydro-naphthalen-4a-yl ester
• 英文别名: [(3R,4aS,8aS)-8a-methyl-5-oxo-3-propan-2-yl-2,3,4,6,7,8-hexahydro-1H-naphthalen-4a-yl] acetate
• CAS: 144127-02-6
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: CCCRIEKWCOIAPY-VNQPRFMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,4aS,8aS)-3-isopropyl-8a-methyl-5-oxo-octahydro-naphthalen-4a-yl ester 在 氨 、 calcium 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以74%的产率得到1-Oxo-7-isopropyl-10-methyl-decalin
  参考文献：
  名称：

  Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.

  摘要：

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00052a036
• 作为产物：
  描述：

  3-((R)-4-Isopropenyl-1-methyl-2-oxo-cyclohexyl)-propionic acid methyl ester 在 palladium on activated charcoal 盐酸 、 lithium aluminium tetrahydride 、 氢气 、 四乙基对甲苯磺酸铵 、 对甲苯磺酸 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 异丙醇 、 苯 为溶剂， 60.0 ℃ 、101.33 kPa 条件下， 反应 11.5h， 生成 Acetic acid (3R,4aS,8aS)-3-isopropyl-8a-methyl-5-oxo-octahydro-naphthalen-4a-yl ester
  参考文献：
  名称：

  Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.

  摘要：

  Electroreduction of gamma and delta-cyano ketones in i-PrOH with Sn cathode gave alpha-hydroxy ketones and their dehydroxylated ketones as the intramolecularly coupled products. Guaiazulene, (-)-valeranone, polyquinanes, dihydrojasmone, methyl dihydrojasmonate, and rosaprostol have been synthesized by utilizing this electroreductive intramolecular coupling of gamma and delta-cyano ketones in one of the key steps. Similarly, electroreduction of a mixture of ketone and nitrile gave the corresponding intermolecularly coupled product. The product obtained by the electroreductive intermolecular coupling of (+)-dihydrocarvone with acetonitrile has been found to be the precursor of an effective chiral ligand for the enantioselective addition of diethylzinc to aldehydes.

  DOI：

  10.1021/jo00052a036