(3aS,6aR)-Hexahydro-pentalene-1,6a-diol | 99115-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,6aR)-Hexahydro-pentalene-1,6a-diol
• 英文别名: (3aS,6aR)-2,3,3a,4,5,6-hexahydro-1H-pentalene-1,6a-diol
• CAS: 99115-04-5
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: AVKSYAUUMDYUDO-YPVSKDHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  10.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (3aS,6aR)-Hexahydro-pentalene-1,6a-diol 在 lithium aluminium tetrahydride 、 甲基磺酰氯 、 三乙胺 作用下， 生成 2,3,4,5,6,6a-hexahydro-1H-pentalen-3a-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：

  (3aRS,6aSR)-6a-hydroxyhexahydropentalen-1(2H)-one 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 (3aS,6aR)-Hexahydro-pentalene-1,6a-diol
  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