2,2-二苯基-2-氟乙醛 | 107365-22-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,2-二苯基-2-氟乙醛
• 英文名称: 2,2-diphenyl-2-fluoroacetaldehyde
• 英文别名: fluorodiphenylacetaldehyde；2-fluoro-2,2-diphenylacetaldehyde
• CAS: 107365-22-0
• 化学式: C₁₄H₁₁FO
• 分子量: 214.239
• InChiKey: VKPVMTLQCCVGIG-UHFFFAOYSA-N

物化性质

• 熔点：
  61-63 °C
• 沸点：
  310.0±42.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 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：

  二苯甲酮 在 silica gel 作用下， 以 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 13.0h， 生成 2,2-二苯基-2-氟乙醛
  参考文献：
  名称：

  通过羰基亲电试剂的氟烷基化制备和官能化单氟和多氟环氧化物

  摘要：

  我们报告了一种新的合成方法，该方法允许氟烷基阴离子合成子和羰基亲电子试剂之间发生串联 1,2-加成和闭环反应，形成氟化环氧化物。我们通过检查氟烷基要求阐明了反应顺序的一般性。这种方法能够获得独特的化合物，这些化合物可以通过开环或开环脱氟功能化反应进行多样化。

  DOI：

  10.1002/chem.202203578

文献信息

• Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines
  作者：A. S. Konev、M. S. Novikov、A. F. Khlebnikov

  DOI：10.1134/s1070428007020224

  日期：2007.2

  N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.
• Preparation of α-fluoroaldehydes and α-fluoroketones using dilute fluorine
  作者：Suzanne T. Purrington、Nicholas V. Lazaridis、Carl L. Bumgardner

  DOI：10.1016/s0040-4039(00)84624-9

  日期：——
• Asymmetric oxidative α-fluorination of 2-alkylphenylacetaldehydes with AgHF2 and ruthenium/PNNP catalysts
  作者：Martin Althaus、Antonio Togni、Antonio Mezzetti

  DOI：10.1016/j.jfluchem.2009.05.008

  日期：2009.8

  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.
• PURRINGTON S. T.; LAZARIDIS N. V.; BUMGARDNER C. L., TETRAHEDRON LETT., 27,(1986) N 24, 2715-2716
  作者：PURRINGTON S. T.、 LAZARIDIS N. V.、 BUMGARDNER C. L.

  DOI：——

  日期：——