(4aS,8aR)-8a-Hydroxy-1-oxo-octahydro-naphthalene-4a-carboxylic acid ethyl ester | 144126-77-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,8aR)-8a-Hydroxy-1-oxo-octahydro-naphthalene-4a-carboxylic acid ethyl ester
• 英文别名: ethyl (4aS,8aR)-8a-hydroxy-8-oxo-2,3,4,5,6,7-hexahydro-1H-naphthalene-4a-carboxylate
• CAS: 144126-77-2
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: ITKPMCOFHWNHEK-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 1-(3-cyanopropyl)-2-oxocyclohexanecarboxylate 在 四乙基对甲苯磺酸铵 作用下， 以 异丙醇 为溶剂， 生成 (4aS,8aR)-8a-Hydroxy-1-oxo-octahydro-naphthalene-4a-carboxylic acid ethyl ester 、 (4aS,8aS)-8a-Hydroxy-1-oxo-octahydro-naphthalene-4a-carboxylic acid ethyl 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