2-fluoro-3,3-dimethyl-2-phenylbutyraldehyde | 1198158-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-fluoro-3,3-dimethyl-2-phenylbutyraldehyde
• 英文别名: 2-Fluoro-3,3-dimethyl-2-phenylbutanal
• CAS: 1198158-13-2
• 化学式: C₁₂H₁₅FO
• 分子量: 194.249
• InChiKey: BWBWOUVIVIGNOZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,3-dimethyl-2-phenylbutanal 在 silver hexafluoroantimonate 、 silver(I) bifluoride 、 [RuCl₂((1S,2S)-N,N'-bis[o-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine)] 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以13%的产率得到2-fluoro-3,3-dimethyl-2-phenylbutyraldehyde
  参考文献：
  名称：

  Asymmetric oxidative α-fluorination of 2-alkylphenylacetaldehydes with AgHF2 and ruthenium/PNNP catalysts

  摘要：

  During attempts directed at epoxide ring opening with different HF sources, we discovered that the Lewis acidic [RuCl(PNNP)](+) (1) or [Ru(OEt2)(2)(PNNP)](2+) (2) catalysts promote the [1,2]-phenyl shift (Meinwald rearrangement) in phenyl-substituted epoxides to give the corresponding 2-alkylphenylacetaldehydes, which are fluorinated at the alpha-position in the presence of silver bifluoride (AgHF2) (PNNP is (1S,2S)-N,N'-bis[o-(diphenylphosphino)benzylidene]cyclohexane-1,2-diamine). The optimization of aldehyde fluorination with PhCH(R)CHO (R = Me, Et, Pr-i, Bu-t) as substrates showed that catalyst [1]SbF6 gives a moderate degree of enantioselectivity (up to 27% ee) and 35% yield. The substrate scope is limited to benzylic aldehydes. The reaction is unprecedented for transition metal catalysts. Circumstantial evidence suggests that the mechanism involves chemical oxidation followed by enantioselective fluorination with F-. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2009.05.008