5-(R/S)-2-isopropylidene-5-<2H3>methyl-<4,4-2H2>cyclohexanone | 244161-40-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(R/S)-2-isopropylidene-5-<2H3>methyl-<4,4-2H2>cyclohexanone
• 英文别名: d5-pulegone
• CAS: 244161-40-8
• 化学式: C₁₀H₁₆O
• 分子量: 157.197
• InChiKey: NZGWDASTMWDZIW-IKISXXDZSA-N

反应信息

• 作为反应物：
  描述：

  5-(R/S)-2-isopropylidene-5-<2H3>methyl-<4,4-2H2>cyclohexanone 在 儿萘酚硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 6,6,7,7,7-Pentadeuterio-isomenthon
  参考文献：
  名称：

  Biogenetic Studies in Mentha × piperita. 1. Deuterium-Labeled Monoterpene Ketones:  Synthesis and Stereoselective Analysis

  摘要：

  Pulegone, menthone, and isomenthone isotopomers are synthesized as regioselectively deuterated d(5)- and d(8)-stereoisomers. Deuterium-labeled menthone and isomenthone enantiomers are analyzed using enantioselective multidimensional gas chromatography/mass spectrometry. The deuterated stereoisomers of menthone and isomenthone are separated from the unlabeled menthone and isomenthone on a glass capillary column, coated with 50% octakis(2,3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin in OV 1701vi as the chiral stationary phase. These deuterium-labeled monoterpene ketones are proved to be highly valuable substrates in biosynthetic studies of terpenoid compounds.

  DOI：

  10.1021/jf990132f
• 作为产物：
  描述：

  d5-isopulegone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以3 mg的产率得到5-(R/S)-2-isopropylidene-5-<2H3>methyl-<4,4-2H2>cyclohexanone
  参考文献：
  名称：

  Biogenetic Studies in Mentha × piperita. 1. Deuterium-Labeled Monoterpene Ketones:  Synthesis and Stereoselective Analysis

  摘要：

  Pulegone, menthone, and isomenthone isotopomers are synthesized as regioselectively deuterated d(5)- and d(8)-stereoisomers. Deuterium-labeled menthone and isomenthone enantiomers are analyzed using enantioselective multidimensional gas chromatography/mass spectrometry. The deuterated stereoisomers of menthone and isomenthone are separated from the unlabeled menthone and isomenthone on a glass capillary column, coated with 50% octakis(2,3-di-O-butyryl-6-O-tert-butyldimethylsilyl)-gamma-cyclodextrin in OV 1701vi as the chiral stationary phase. These deuterium-labeled monoterpene ketones are proved to be highly valuable substrates in biosynthetic studies of terpenoid compounds.

  DOI：

  10.1021/jf990132f