(3aR,3bS,6aR,7aR)-3b-hydroxy-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-4-one | 144127-08-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,3bS,6aR,7aR)-3b-hydroxy-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-4-one
• CAS: 144127-08-2
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: OFTSTXNUTWWRNF-CDLYGTGVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  (3aR,3bS,6aR,7aR)-3b-hydroxy-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-4-one 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 三乙基硼氢化锂 、 对甲苯磺酸 、 锌 作用下， 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 15.5h， 生成 cis-transoid-cis-tricyclo[6.3.0.0^2,6]undecane
  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-[(3aS,6aS)-3-oxo-2,3a,4,5,6,6a-hexahydro-1H-pentalen-2-yl]propanenitrile 在 四乙基对甲苯磺酸铵 作用下， 以 异丙醇 为溶剂， 生成 (3aR,3bS,6aR,7aR)-3b-hydroxy-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-4-one 、 (3aS,3bS,6aR,7aS)-3b-hydroxy-2,3,3a,5,6,6a,7,7a-octahydro-1H-cyclopenta[a]pentalen-4-one
  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