2805-22-3

Upstream product

• 542-75-6 E/Z-1,3-Dichloropropene 
• 22675-65-6 1-chloro-3-fluoro-propene 
• 118373-19-6 propargyl 2-chloro-2,2-difluoroacetate 
• 100312-94-5 C₃H₂⁽³⁾HF 
• 107-19-7 propargyl alcohol 
• 106-96-7 propargyl bromide 

Downstream Products

• 1268257-56-2 3-benzo[1,3]dioxol-5-yl-4-{3-[2-(2-{2-[2-(4-fluoromethyl-1,2,3-triazol-1-yl)ethoxy]ethoxy}ethoxy)ethoxy]-4,5-dimethoxybenzyl}-5-hydroxy-5-(4-methoxyphenyl)-5H-furan-2-one 

Relevant academic research and scientific papers

Efficient protocol for the SO2F2-mediated deoxyfluorination of aliphatic alcohols

Alkyl fluorides are prevalent in both the pharmaceutical and agrochemical industries. As such, there has been significant interest over the past 40 years in the development of new synthetic methods to access these important fluorinated motifs. Herein we report the sulfuryl fluoride-mediated deoxyfluorination of alcohols using room temperature reaction conditions in only an hour. A wide range of primary aliphatic alcohols were efficiently converted to the corresponding fluoride in 46-70% isolated yields. Secondary alcohols were also effectively deoxyfluorinated in 50–92% yields. Chiral secondary alcohols were cleanly converted to the corresponding alkyl fluoride with only a minor deterioration of the enantioenrichment. A steroid derivative also underwent deoxyfluorination in 50% yield and 5.9:1 dr, with the major product resulting from net inversion of the stereocenter.

METHOD AND REAGENT FOR DEOXYFLUORINATION

A safe, simple, and selective method and reagent for deoxyfluorination is disclosed. With the method and reagent disclosed herein, organic compounds such as carboxylic acids, carboxylates, carboxylic acid anhydrides, aldehydes, and alcohols can be fluorinated by using the most common nucleophilic fluorinating reagents and electron deficient fluoroarenes as mediators under mild conditions, giving corresponding fluoroorganic compounds in excellent yield with a wide range of functional group compatibility and easy product purification. For example, directly utilizing KF for deoxyfluorination of carboxylic acids provides the most economical and the safest pathway to access acyl fluorides, key intermediates for syntheses of peptide, amide, ester, and dry fluoride salts.

Development and evaluation of endothelin-A receptor (radio)ligands for positron emission tomography

The expression and function of endothelin (ET) receptors are abnormal in cardiovascular diseases, tumor progression, and tumor metastasis. A previously reported promising radioligand for positron emission tomography (PET) based on the non-peptide ETA receptor antagonist PD 156707 showed specific binding to target receptors in the myocardium but high accumulation in bile and intestine, probably because of its high lipophilicity. In this study we describe the synthesis of a series of fluorinated derivatives with hydrophilic building blocks. All compounds were evaluated as high affinity ETA receptor ligands (16, 17, 23-26, Ki = 1.4-7.9 nM) with high subtype selectivity over the ETB receptor. [18F]3-Benzo[1,3] dioxol-5-yl-4-{3-[1-(2-{2-[2-(2-fluoroethoxy)ethoxy]ethoxy}ethyl)-1H-[1,2,3] triazol-4-ylmethoxy]-4,5-dimethoxybenzyl}-5-hydroxy-5-(4-methoxyphenyl) -5H-furan-2-one ([18F]17) was synthesized as one of the radioligands of this series that possesses a higher hydrophilicity and an excellent stability in human serum. Improved clearance properties and specific uptake in target organs have been confirmed by biodistribution studies and small animal PET imaging.

Novel Synthesis of 2,2,2-Trifluoroethyl Compounds from Homoallylic Alcohols: A Copper(I) Iodide-initiated Trifluoromethyl-Dehydroxylation Process

Benzyl, prop-2-enyl and allyl chlorodifluoroacetates 3a, bromodifluoroacetates 3b or fluorosulfonyldifluoroacetates 3c, when decomposed in the presence of 1 equivalent of copper(I) iodide at an appropriate temperature in dimethylformamide, gave the corresponding trifluoromethyl derivatives in good to excellent yields.The products can also be obtained directly by ester exchange of XCF2CO2Et (X = FSO2, Cl, Br) 6 and the corresponding alcohols in the presence of KF and CuI.A trifluoromethylation-dehydroxylation mechanism, initiated by CuI, is proposed.

Rates of Base-Catalyzed Hydrogen Exchange of Terminal Acetylenes in Aqueous Solution. Absence of Resonance Interaction

Rates of detritiation of 13 monosubstituted acetylenes labeled at the acetylenic hydrogen position were measured in aqueous amine buffer solution at 25 deg C, and hydroxide ion catalytic coefficients were evaluated.These rate constants, plus a few additional values from the literature, give a good correlation against inductive or field substituent constants: log(kHO-/M-1s-1) = 1.46+/-0.12 + (8.00+/-0.50)?I.This correlation is not improved by addition of resonance substituted constants, and the coefficients of the resonance term in two different dual parameter (resonance plus field) treatments of the data are in fact zero.