357-77-7

Usage

Molecular weight

234.24 g/mol

Functional group

Propargylic alcohol

Structural feature

Two 4-fluorophenyl substituents attached to the carbon-carbon triple bond

Application

Organic synthesis and medicinal chemistry

Potential use

Development of pharmaceuticals and agrochemicals

Utility

Building block for the synthesis of various functional molecules and materials in chemical research and industry

InChI:InChI=1/C15H10F2O/c1-2-15(18,11-3-7-13(16)8-4-11)12-5-9-14(17)10-6-12/h1,3-10,18H

Upstream product

• 65032-27-1 ethynylmagnesium chloride 
• 345-92-6 4,4'-Difluorobenzophenone 
• 74-86-2 acetylene 
• 4301-14-8 acetylenemagnesium bromide 
• 1066-54-2 trimethylsilylacetylene 
• 1391868-38-4 C₁₈H₁₈F₂OSi 

Downstream Products

• 10087-77-1 N-Cyclohexyl-carbamidsaeure-<1,1-bis-(4-fluor-phenyl)-propin-(2)-ylester> 
• 21200-17-9 N-Cyclopentyl-carbaminsaeure-<3,3-di-(p-fluorphenyl)-propin-(1)-yl-(3)>-ester 
• 20929-99-1 N-Cycloheptyl-carbaminsaeure-<3.3-di-(4-fluor-phenyl)-propin-(1)-yl-(3)>-ester 
• 853305-74-5 5-methoxycarbonyl-3,3-(4,4'-difluorophenyl)-3H-naphtho[2,1-b]pyrane 
• 1191071-22-3 2,2-bis(4-fluorophenyl)-6-[(methoxycarbonyl)methyl]-2H-1-benzopyran 
• 1191071-19-8 3,3-bis(4-fluorophenyl)-8-(methoxycarbonyl)-3H-naphtho[2,1-b]pyran 
• 1191071-23-4 2,2-bis(4-fluorophenyl)-6-({[(9H-fluoren-9-yl)methoxycarbonyl]amino}methyl)-2H-1-benzopyran 
• 6175-14-0 1,1-bis-(4-fluorophenyl)ethene 
• 1266134-11-5 1,1-bis(4-fluorophenyl)-2-oxopropyl benzoate 
• 1287687-03-9 [Ru(C₃(4-flluorophenyl)2)(indenyl)(PPh₃)P(OC₁₀H₆)2N(CH₂Ph)2]PF₆ 
• 1393370-75-6 (4-(2,2-bis(4-fluorophenyl)vinyl)-2,5-diphenylfuran-3-yl)(phenyl)methanone 
• 1393371-13-5 2,3-bis(4-fluorophenyl)-5-phenylfuran 
• 1393370-57-4 1,1-bis(4-fluorophenyl)-4-phenylbut-2-yne-1,4-diol 
• 1588972-13-7 5,5-bis(4-fluorophenyl)-3,4,4'-triiodo-3'-(4-methoxyphenyl)-5H-spiro[furan-2,1'-isochromene] 

Relevant academic research and scientific papers

Mechanosynthesis of Odd-Numbered Tetraaryl[n]cumulenes

A mechanochemical synthesis of one-dimensional carbon allotrope carbyne model compounds, namely tetraaryl[n]cumulenes (n=3, 5) was realized. Central for the mechanosynthesis of the cumulenic carbon nanostructures were the development of a mechanochemical Favorskii alkynylation-type reaction and the implementation of a solvent-free, acid-free reductive elimination with tin(II) chloride by ball milling.

Design and Synthesis of Quenched Activity-based Probes for Diacylglycerol Lipase and α,β-Hydrolase Domain Containing Protein 6

Diacylglycerol lipases (DAGL) are responsible for the biosynthesis of the endocannabinoid 2-arachidonoylglycerol. The fluorescent activity-based probes DH379 and HT-01 have been previously shown to label DAGLs and to cross-react with the serine hydrolase ABHD6. Here, we report the synthesis and characterization of two new quenched activity-based probes 1 and 2, the design of which was based on the structures of DH379 and HT-01, respectively. Probe 1 contains a BODIPY-FL and a 2,4-dinitroaniline moiety as a fluorophore–quencher pair, whereas probe 2 employs a Cy5-fluorophore and a cAB40-quencher. The fluorescence of both probes was quenched with relative quantum yields of 0.34 and 0.0081, respectively. The probes showed target inhibition as characterized in activity-based protein profiling assays using human cell- and mouse brain lysates, but were unfortunately not active in living cells, presumably due to limited cell permeability.

Metal- and Acid-Free Methyl Triflate Catalyzed Meyer-Schuster Rearrangement

A novel metal- and acid-free preparation of synthetically useful α,β-unsaturated carbonyl compounds from propargyl alcohols has been realized. This Meyer-Schuster rearrangement process is effectively catalyzed by methyl triflate (20 mol%) to prepare a broad scope of conjugated E -enals and E -enones generally in good to excellent yields (up to 90%). This reaction procedure operates under mild conditions (70 °C), in air, with short reaction times (1 h). Moreover, a carbocation intermediate trapped by the solvent 2,2,2-trifluoroethanol was isolated during this transformation.

TRIAZOLE DAGL(α) INHIBITORS

Provided herein are triazole compounds and pharmaceutical compositions comprising said compounds useful as modulators of DAGL(α) and DAGL(β). In some embodiments, the compounds described herein are selective DAGL(α) inhibitors. Furthermore, the subject co

Convenient and highly efficient routes to 2 H-chromene and 4-chromanone derivatives: Iodine-promoted and p-toluenesulfonic acid catalyzed cascade cyclizations of propynols

A convenient strategy is presented for the easy preparation of a series of 2 H-chromenes under mild conditions through iodocyclization of readily accessible propynols. In addition, various 4-chromanones can be synthesized through a p-toluenesulfonic acid catalyzed cascade cyclization with high efficiency (yields up to 99%). Our developed reaction systems are proven to have good functional-group applicability and can be scaled up to gram quantities in satisfactory yields. These systems also provide a new synthetic strategy for two types of important flavonoid skeleton without using costly and toxic metal catalysts. Additionally, the resulting halides could be further exploited in subsequent palladium-catalyzed coupling reactions, so these compounds could act as potential intermediates for the construction of some valuable drug molecules.

Facile synthesis of halogenated spiroketals via a tandem iodocyclization

A strategy for the synthesis of spiroketal compounds through a tandem iodocyclization of 1-(2-ethynylphenyl)-4-hydroxybut-2-yn-1-one derivatives is presented. This reaction could proceed under very mild conditions in a short time and avoid the use of expensive and toxic metal catalysts. Moreover, the resulting halides can be further exploited by subsequent palladium-catalyzed coupling reactions, which act as the important intermediates for building other valuable compounds.

POLYMER PARTICLES OR NANO-VECTORS AND USE THEREOF AS A DRUG AND/OR DIAGNOSTIC AGENT

Novel polymer nanovectors or particles and use thereof as medication and/or diagnostic agents.

Bronsted acid-catalyzed cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds to tri- and tetrasubstituted furans

A Bronsted acid-catalyzed method to prepare tri- and tetrasubstituted furans efficiently from cycloisomerization of but-2-yne-1,4-diols with or without 1,3-dicarbonyl compounds is described. By taking advantage of the orthogonal modes of reactivity of the alcoholic substrate through slight modification of the reaction conditions, a divergence in product selectivity was observed. At room temperature, p-TsOH?H 2O-mediated tandem alkylation/cycloisomerization of the propargylic 1,4-diol with the β-dicarbonyl compound was found to selectively occur to provide the tetrasubstituted furan product. On the other hand, increasing the reaction temperature to 80 °C was discovered to result in preferential p-TsOH?H2O-catalyzed dehydrative rearrangement of the unsaturated alcohol and formation of the 2,3,5-trisubstituted furan adduct.

Synthesis of novel photochromic pyrans via palladium-mediated reactions

Photochromic pyrans for applications in material and life sciences were synthesized via palladium-mediated cyanation, carbonylation and Sonogashira cross-coupling starting from bromo-substituted naphthopyran 1 and benzopyrans 2a/b. A novel photoswitchable benzopyran-based ?-amino acid 6 for Fmoc-based solid-phase peptide synthesis is presented. The photochromic behaviour of the 3-cyano-substituted benzopyran 5a was investigated by time-resolved absorption spectroscopy in the picosecond time domain.

Synthesis and photochromic behavior of fluoro 2H-1-benzopyrans containing a carbazole moiety

The synthesis of new photochromic 2,2-di(4′-fluoro-phenyl)-2H-1- benzopyrans fused to an indole moiety is described. Spectrokinetic data (λmax of colored form, colorability and rate constant of bleaching) obtained by UV-Visible spectroscopy and the struct