ethyl (3aS,7aS)-7a-hydroxy-1-oxo-2,3,4,5,6,7-hexahydroindene-3a-carboxylate | 144126-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (3aS,7aS)-7a-hydroxy-1-oxo-2,3,4,5,6,7-hexahydroindene-3a-carboxylate
• CAS: 144126-75-0
• 化学式: C₁₂H₁₈O₄
• 分子量: 226.273
• InChiKey: ANFDSLYHZQRRPW-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  ethyl (3aS,7aS)-7a-hydroxy-1-oxo-2,3,4,5,6,7-hexahydroindene-3a-carboxylate 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 cis-1-Hydroxy-6-methylbicyclo<4.3.0>nonane
  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-(2-cyanoethyl)-2-oxocyclohexanecarboxylate 在 samarium diiodide 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到ethyl (3aS,7aS)-7a-hydroxy-1-oxo-2,3,4,5,6,7-hexahydroindene-3a-carboxylate
  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