(3aR,6aR)-6a-hydroxy-5,5-dimethyl-3,3a,4,6-tetrahydro-2H-pentalen-1-one | 144127-06-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6aR)-6a-hydroxy-5,5-dimethyl-3,3a,4,6-tetrahydro-2H-pentalen-1-one
• CAS: 144127-06-0
• 化学式: C₁₀H₁₆O₂
• 分子量: 168.236
• InChiKey: SCJWYXVBADBSRF-GMSGAONNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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,6aR)-6a-hydroxy-5,5-dimethyl-3,3a,4,6-tetrahydro-2H-pentalen-1-one 在 甲酸 、 硫酸 作用下， 反应 0.25h， 以83%的产率得到7,7-dimethylbicyclo<3.3.0>oct-1(5)en-2-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
• 作为产物：
  描述：

  3,3-二甲基-环戊酮 在 sodium hydride 、 四乙基对甲苯磺酸铵 、 三乙胺 作用下， 以 乙醇 、 水 、 异丙醇 、 苯 为溶剂， 反应 132.0h， 生成 (3aR,6aR)-6a-hydroxy-5,5-dimethyl-3,3a,4,6-tetrahydro-2H-pentalen-1-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