(3aR,7aR)-1,2,3,3a,5,6,7,7a-octahydrocyclopenta[a]pentalen-4-one | 119245-21-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,7aR)-1,2,3,3a,5,6,7,7a-octahydrocyclopenta[a]pentalen-4-one
• CAS: 119245-21-5
• 化学式: C₁₁H₁₄O
• 分子量: 162.232
• InChiKey: DVUBXRFCILBWAF-VXNVDRBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3aR,7aR)-1,2,3,3a,5,6,7,7a-octahydrocyclopenta[a]pentalen-4-one 在 palladium on activated charcoal 吡啶 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 氢气 、 三乙基硼氢化锂 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 15.0h， 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：

  (3aS,3bS,6aS,7aR)-3a-Hydroxy-decahydro-cyclopenta[a]pentalen-3-one 在 甲酸 、 硫酸 作用下， 反应 0.25h， 以85%的产率得到(3aR,7aR)-1,2,3,3a,5,6,7,7a-octahydrocyclopenta[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