1-cyclohexyl-2,2-difluoro-1-hydroxyheptan-3-one | 263898-44-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-cyclohexyl-2,2-difluoro-1-hydroxyheptan-3-one
• CAS: 263898-44-8
• 化学式: C₁₃H₂₂F₂O₂
• 分子量: 248.313
• InChiKey: FEPUDNFJXJMTOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  6
• 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：
  4

反应信息

• 作为产物：
  描述：

  2-(3-benzyl-2-butyl-2,3-dihydrobenzo[d]oxazol-2-yl)-1-cyclohexyl-2,2-difluoroethanol 在 盐酸 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以99%的产率得到1-cyclohexyl-2,2-difluoro-1-hydroxyheptan-3-one
  参考文献：
  名称：

  A rapid and convergent synthesis of α,α-difluoro-β-hydroxyketones through regiospecific defluorinative alkylation reaction

  摘要：

  Both the defluorinative alkylation reaction of trifluoroacetaldehyde N,O-acetals using alkyllithiums and the following C-C bond formation with carbonyls as electrophiles were accelerated by a suitable diamine additive such as (-)-sparteine to give alpha,alpha-difluoro-beta-hydroxyketone N,O-acetal products in an excellent yield. We also found that N-benzyl-N,O-acetal group of the resultant products can be removed under palladium-catalyzed hydrogenolysis conditions giving rise to the corresponding alpha,alpha-difluoro-beta-hydroxyketones. The present two-step procedure is a useful and novel synthetic approach for functionalized alpha,alpha-difluoroketones. (C) 2010 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2010.03.018

文献信息

• Preparation of optically active α,α-difluoro-β-hydroxyketones
  作者：Katsuhiko Iseki、Daisuke Asada、Yoshichika Kuroki

  DOI：10.1016/s0022-1139(99)00033-0

  日期：1999.7

  The stereoselective synthesis of α,α-difluoro-β-hydroxyketones of high enantiomeric purity is described starting from optically active α,α-difluoro-β-hydroxy esters. The esters were converted to the corresponding N-methoxy-N-methyl amides, which were treated with Grignard and organolithium reagents to provide the α,α-difluoro-β-hydroxyketones with up to 100% ee.

  从光学活性的α，α-二氟-β-羟基酯开始描述了高对映体纯度的α，α-二氟-β-羟基酮的立体选择性合成。将酯转化为相应的N-甲氧基-N-甲基酰胺，将其用格利雅（Grignard）和有机锂试剂处理，以提供具有高达100％ee的α，α-二氟-β-羟基酮。