4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid, 1,1-dimethylethyl ester | 106893-76-9

• 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: 4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid, 1,1-dimethylethyl ester
• 英文别名: tert-butyl 4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoate；Tert-butyl 4,4,4-trifluoro-3-oxo-2-(triphenyl-lambda5-phosphanylidene)butanoate；tert-butyl 4,4,4-trifluoro-3-oxo-2-(triphenyl-λ5-phosphanylidene)butanoate
• CAS: 106893-76-9
• 化学式: C₂₆H₂₄F₃O₃P
• 分子量: 472.444
• InChiKey: QWYWJWNNUOOINY-UHFFFAOYSA-N

物化性质

• 熔点：
  126.5-127.5 °C(Solv: methanol (67-56-1); water (7732-18-5))
• 沸点：
  515.6±60.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid, 1,1-dimethylethyl ester 在 potassium carbonate 作用下， 反应 5.0h， 以21%的产率得到tert-butyl 4,4,4-trifluorobutynoate
  参考文献：
  名称：

  Palladium-Catalyzed Desymmetrization of Silacyclobutanes with Alkynes: Enantioselective Synthesis of Silicon-Stereogenic 1-Sila-2-cyclohexenes and Mechanistic Considerations

  摘要：

  A palladium-catalyzed enantioselective desymmetrization of silacyclobutanes with alkynes has been developed to give silicon-stereogenic 1-sila-2-cyclohexenes with high enantioselectivity. The products thus obtained undergo further derivatizations with complete stereoselectivity, and a new catalytic cycle involving alkyne coordination (oxidative cyclization)-transmetalation (sigma-bond metathesis)-reductive elimination has also been proposed.

  DOI：

  10.1021/ol301191u
• 作为产物：
  描述：

  三苯基膦 在 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 4,4,4-trifluoro-3-oxo-2-(triphenylphosphoranylidene)butanoic acid, 1,1-dimethylethyl ester
  参考文献：
  名称：

  Direct synthesis of .beta.-ketomethylenetriphenylphosphoranes from readily available phosphonium salts

  摘要：

  DOI：

  10.1021/jo00258a035

文献信息

• 1,3-Dipolar cycloaddition reactions of pyrazolidinium ylides with acetylenes. Synthesis of a new class of antibacterial agents
  作者：Louis N. Jungheim、Sandra K. Sigmund

  DOI：10.1021/jo00227a013

  日期：1987.9
• Shen, Yanchang; Gao, Shu, Journal of the Chemical Society. Perkin transactions I, 1994, # 11, p. 1473 - 1476
  作者：Shen, Yanchang、Gao, Shu

  DOI：——

  日期：——
• A stereoselective synthesis of (Z)- and (E)-trifluoromethylated .alpha.,.beta.-unsaturated esters via intramolecular Wittig reaction
  作者：Yanchang Shen、Shu Gao

  DOI：10.1021/jo00069a014

  日期：1993.8

  Fluorinated dicarbonyl triphenylphosphoranes 1 reacted with a variety of Grignard reagents to give beta-oxido alidase 2. Treatment of 2 with acetic acid or saturated aqueous methylamine hydrochloride, followed by elimination of triphenylphosphine oxide, gave trifluoromethylated alpha,beta-unsaturated esters with the Z-isomers being the major products; while treatment of 2 with 5% aqueous hydrochloric acid under the same conditions afforded predominately E-isomers of the title compounds.
• Stereoselective synthesis of trifluoromethylated α-chloro-α,β-unsaturated esters and nitriles
  作者：Yanchang Shen、Shu Gao

  DOI：10.1039/p19960002531

  日期：——

  A stereoselective synthesis of trifluordmethylated alpha-chloro-alpha,beta-unsaturated esters and nitriles by the reaction of fluorinated ylide-anion resulting from nucleophilic addition of organolithium or Grignard reagents to trifluoromethylated phosphoranes with N-chlorosuccinimide is described.
• Shen Yanchang, Gao Shu, J. Chem. Soc. Perkin Trans, (1994) N 11, S 1473-1475
  作者：Shen Yanchang, Gao Shu

  DOI：——

  日期：——