7,7-dimethylbicyclo<3.3.0>oct-1(5)en-2-one | 83180-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,7-dimethylbicyclo<3.3.0>oct-1(5)en-2-one
• 英文别名: 5,5-Dimethyl-2,3,4,6-tetrahydropentalen-1-one
• CAS: 83180-75-0
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: HZEKTHXIYPIREL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 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：

  7,7-dimethylbicyclo<3.3.0>oct-1(5)en-2-one 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以90%的产率得到7,7-Dimethyl-cis-bicyclo<3.3.0>octan-2-on
  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：

  (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

文献信息

• Triquinane sesquiterpenes. An iterative, highly stereocontrolled synthesis of (.+-.)-silphinene
  作者：Leo A. Paquette、Andrea Leone-Bay

  DOI：10.1021/ja00363a024

  日期：1983.11

  Synthese en 15 etapes a partir de la dimethyl-4,4 cyclopentene-2one. La formation des noyaux cyclopentanes est obtenue par une double addition d'un reactif organocuivrique fonctionnalise suivie d'une cyclisation aldol

  合成这些 en 15 etapes a partir de la dimethyl-4,4 cyclopentene-2one。La Formation des noyaux cyclopentanes est obtenue par une double added d'un reactif Organiccuivrique fonctionnalise suivie d'une cyclisation aldol
• Rearrangements initiated by trimethylsilyl iodide: ready deoxygenative rearrangement of bicyclo[4.2.0]octane-2,5-diones to bicyclo[3.3.0]oct-1(5)-en-2-ones
  作者：Kaoru Sasaki、Takahiro Kushida、Masahiko Iyoda、Masaji Oda

  DOI：10.1016/s0040-4039(00)87276-7

  日期：1982.1

  Reaction of bicyclo[4.2.0]octane-2,5-diones with trimethylsilyl iodide gave bicyclo[3.3.0]oct-1(5)-en-2-ones by a clean reductive rearrangement in good yields, providing a simple and effecient synthetic method for the enones.

  双环[4.2.0]辛烷-2,5-二酮与碘化三甲基甲硅烷基的反应通过干净的还原重排以良好的收率得到双环[3.3.0] oct-1（5）-en-2-one，提供了简单而又烯酮的有效合成方法。
• SASAKI, KAORU;KUSHIDA, TAKAHIRO;IYODA, MASAHIKO;ODA, MASAJI, TETRAHEDRON LETT., 1982, 23, N 20, 2117-2120
  作者：SASAKI, KAORU、KUSHIDA, TAKAHIRO、IYODA, MASAHIKO、ODA, MASAJI

  DOI：——

  日期：——