4-(cyclohexylhydroxymethyl)-3-hexanone | 173975-73-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(cyclohexylhydroxymethyl)-3-hexanone
• 英文别名: 4-[Cyclohexyl(hydroxy)methyl]hexan-3-one
• CAS: 173975-73-0
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: KDNODLJJTDGGBU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-己烯-3-酮 、 环己烷基甲醛 生成 4-(cyclohexylhydroxymethyl)-3-hexanone 、 4-(cyclohexylhydroxymethyl)-3-hexanone
  参考文献：
  名称：

  Reactions of Tin(IV) Enolates Obtained from O-Stannyl Ketyls under Neutral Free Radical Conditions

  摘要：

  Under mild and neutral free radical conditions, an alpha,beta-unsaturated ketone reacted with tributyltin hydride to produce an intermediate resonance-stabilized allylic O-stannyl ketyl. Upon subsequent hydrogen atom abstraction, a tin(IV) enolate was afforded which could be quenched with a variety of electrophiles and form new carbon-carbon bonds. Aldehydes react to produce aldol-type products and both intramolecular and intermolecular carbonyl addition reactions were investigated using this strategy. Using similar methodology, the tin(TV) enolate could be quenched in the presence of HMPA with various alkyl halides and alpha,beta-unsaturated carbonyl compounds (Michael accepters) to yield alkylated products in good yields. These reactions represent a very mild regioselective alternative to metal enolate formation which usually requires strong bases such as LDA or strongly reductive dissolving metal conditions to achieve success. New carbon skeletons for natural product synthesis can be readily constructed using this chemically neutral approach.

  DOI：

  10.1021/jo960639e