1-Oxo-3a-methyl-perhydroinden | 16938-81-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-Oxo-3a-methyl-perhydroinden
• 英文别名: 3a-methyl-3,4,5,6,7,7a-hexahydro-2H-inden-1-one
• CAS: 16938-81-1
• 化学式: C₁₀H₁₆O
• 分子量: 152.236
• InChiKey: PIYXYHCDERFJBJ-UHFFFAOYSA-N

物化性质

• 沸点：
  223.7±8.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  11
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3,4,5,6,7,8-hexahydro-2(1H)-naphthalenone 在 Lindlar's catalyst 氢溴酸 、 氢气 作用下， 以 溶剂黄146 、 叔丁醇 为溶剂， 生成 1-Oxo-3a-methyl-perhydroinden
  参考文献：
  名称：

  β，γ-不饱和环酮的光化学重排

  摘要：

  β，γ-不饱和环酮I和IV的辐照导致异常重排，产生共轭的环丙基酮IIa和Va。光产物的结构由其光谱性质推导得出，并通过将光产物转化为已知结构的化合物来证明。光产物Va已转换为10α甲基A-nor类固醇。讨论了反应的可能机理。

  DOI：

  10.1016/s0040-4020(01)96846-2

文献信息

• Electroorganic chemistry. 140. Electroreductively promoted intra- and intermolecular couplings of ketones with nitriles.
  作者：Tatsuya Shono、Naoki Kise、Taku Fujimoto、Naoto Tominaga、Hiroshi Morita

  DOI：10.1021/jo00052a036

  日期：1992.12

  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.
• A photochemical rearrangement of β,γ-unsaturated cyclic ketones
  作者：J.R. Williams、H. Ziffer

  DOI：10.1016/s0040-4020(01)96846-2

  日期：1968.1

  γ-unsaturated cyclic ketones I and IV results in an unusual rearrangement yielding the conjugated cyclopropyl ketones IIa and Va. The structures of the photoproducts were deduced from their spectroscopic properties and proved by converting the photoproducts to compounds of known structure. The photoproduct Va has been converted to a 10α methyl A-nor steroid. A possible mechanism for the reaction is discussed

  β，γ-不饱和环酮I和IV的辐照导致异常重排，产生共轭的环丙基酮IIa和Va。光产物的结构由其光谱性质推导得出，并通过将光产物转化为已知结构的化合物来证明。光产物Va已转换为10α甲基A-nor类固醇。讨论了反应的可能机理。