Ethyl 2-(bis(2,2,2-trifluoroethoxy)phosphoryl)propanoate

This substance is typically encountered as a clear, colorless to pale straw-colored oil at ambient temperature. Its molecular composition is C9H13F6O5P, with a formula weight of approximately 346.2. The boiling point is elevated but can be distilled under reduced pressure. It is soluble in a broad range of organic solvents, including alcohols, chlorinated solvents, and aromatic hydrocarbons, while being essentially immiscible with water. The molecule incorporates two strongly electron-withdrawing trifluoroethyl groups attached to a phosphonate center, which significantly influences its chemical behavior. It should be stored in a tightly sealed vessel under a dry inert atmosphere and protected from light, preferably under refrigeration. Contact with strong bases or oxidizers is not recommended.

This compound is a specialized and highly reactive phosphonate ester, meticulously designed for use in the Horner–Wadsworth–Emmons olefination reaction. Its defining structural feature is the pair of 2,2,2-trifluoroethyl groups bonded to the phosphorus atom. The immense electron-withdrawing power of these fluorinated substituents dramatically increases the acidity of the adjacent -hydrogen on the propionate ester moiety. This allows for the generation of a stabilized phosphonate carbanion under exceptionally mild basic conditions. This carbanion then reacts with carbonyl compounds (aldehydes or ketones) to form , -unsaturated esters with a high℃of stereocontrol, predominantly yielding the thermodynamically favored (E)-isomer. The reagent thus provides a powerful and reliable method for constructing geometrically defined alkenes, a critical transformation in the synthesis of complex natural products and pharmaceuticals.

The primary and most significant application of this reagent is in the stereoselective construction of carbon-carbon double bonds. It is a cornerstone tool for synthetic chemists aiming to install (E)- , -unsaturated esters within a target molecule. This transformation is pivotal in the total synthesis of polyketide natural products, macrolides, and other complex architectures where the precise geometry of a double bond dictates the three-dimensional shape and biological function of the final compound.

Beyond its role in olefination, this molecule can serve as a vehicle for incorporating fluorinated motifs into larger structures. The bis(trifluoroethyl)phosphonate group, after its use in a Horner-Wadsworth-Emmons reaction, can be transformed or retained to impart unique physicochemical properties to the final product. The presence of fluorine atoms can profoundly enhance a molecule's metabolic stability, lipophilicity, and ability to engage in specific binding interactions with biological targets, making this a valuable strategy in medicinal chemistry.

In the field of materials science, this phosphonate ester is a valuable precursor for synthesizing functional polymers and surface modifiers. The trifluoroethyl groups are known to impart low surface energy, exceptional chemical resistance, and high thermal stability to polymeric materials. It can be used to create specialty coatings, advanced sealants, and other high-performance materials where a fluorinated segment is required to achieve specific surface or bulk properties.

The unique electronic characteristics of this reagent make it an excellent model compound for fundamental research. Physical organic chemists use it to study the effect of strongly electron-withdrawing substituents on the stability and reactivity of phosphonate-stabilized carbanions. Investigating the kinetics and stereoselectivity of its reactions provides deep insights into the factors governing the Horner-Wadsworth-Emmons reaction, which in turn guides the development of new and more sophisticated synthetic methodologies.

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