(4aS,8aS)-8a-Hydroxy-1-oxo-octahydro-naphthalene-4a-carboxylic acid ethyl ester | 144126-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aS,8aS)-8a-Hydroxy-1-oxo-octahydro-naphthalene-4a-carboxylic acid ethyl ester
• 英文别名: ethyl (4aS,8aS)-8a-hydroxy-8-oxo-2,3,4,5,6,7-hexahydro-1H-naphthalene-4a-carboxylate
• CAS: 144126-76-1
• 化学式: C₁₃H₂₀O₄
• 分子量: 240.299
• InChiKey: ITKPMCOFHWNHEK-CHWSQXEVSA-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

• 作为反应物：
  描述：

  (4aS,8aS)-8a-Hydroxy-1-oxo-octahydro-naphthalene-4a-carboxylic acid ethyl ester 在 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙基硼氢化锂 、 甲基磺酰氯 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (4as,8ar)-8a-methyloctahydronaphthalen-4a(2H)-ol
  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：

  ethyl 1-(3-cyanopropyl)-2-oxocyclohexanecarboxylate 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以37%的产率得到(4aS,8aS)-8a-Hydroxy-1-oxo-octahydro-naphthalene-4a-carboxylic acid ethyl ester
  参考文献：
  名称：

  Intramolecular Ketone−Nitrile Reductive Coupling Reactions Promoted by Samarium(II) Iodide

  摘要：

  Samarium(II) iodide (SmI2) has been successfully utilized as a reducing agent for the intramolecular coupling of ketones with nitriles. The use of visible light to promote the reductive coupling represents an improvement over previously reported protocols. The procedure also avoids overreduction of the resulting alpha-hydroxy ketones. Monocyclic, fused bicyclic, and bridged bicyclic alpha-hydroxy ketones composed of a number of substitution patterns have been synthesized in moderate to excellent yield via this method. A sequential reaction consisting of a nucleophilic acyl substitution followed by a ketyl-nitrile coupling has also been accomplished.

  DOI：

  10.1021/jo981537m

文献信息

• Electroorganic Chemistry. 144. Electroreductive Coupling of Ketones with O-Methyl Oximes, N,N-Dimethylhydrazones, and Nitrones. A Convenient Route to Synthesis of .beta.-Amino Alcohol
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Ayuko Yamanami、Ryoji Nomura

  DOI：10.1021/jo00086a023

  日期：1994.4

  The intermolecular coupling of a variety of ketones with some types of O-methyl oximes took place when a mixture of both components was electrochemically reduced in i-PrOH with an Sn cathode. The product, beta-methoxyamino alcohol was easily converted to beta-amino alcohol by simple reduction. A chiral ligand effective for the enantioselective addition of diethylzinc to an aldehyde was easily obtained from the product formed by the electroreductive coupling of (-)-menthone with O-methylacetaldoxime. The intermolecular coupling of a ketone with a N,N-dimethylhydrazone or nitrone was also promoted by the electroreduction. Furthermore, the electroreductive coupling of a carbonyl group with an intramolecular O-methyl oxime moiety gave the corresponding cyclized product stereoselectively.
• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  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.
• Intramolecular Ketone−Nitrile Reductive Coupling Reactions Promoted by Samarium(II) Iodide
  作者：Gary A. Molander、Chad N. Wolfe

  DOI：10.1021/jo981537m

  日期：1998.11.1

  Samarium(II) iodide (SmI2) has been successfully utilized as a reducing agent for the intramolecular coupling of ketones with nitriles. The use of visible light to promote the reductive coupling represents an improvement over previously reported protocols. The procedure also avoids overreduction of the resulting alpha-hydroxy ketones. Monocyclic, fused bicyclic, and bridged bicyclic alpha-hydroxy ketones composed of a number of substitution patterns have been synthesized in moderate to excellent yield via this method. A sequential reaction consisting of a nucleophilic acyl substitution followed by a ketyl-nitrile coupling has also been accomplished.