4200-06-0

Usage

Uses

Used in Organic Synthesis:
1-Ethynyl-4-phenoxybenzene is used as a key intermediate in the Sonogashira coupling reactions, which are palladium-catalyzed cross-coupling reactions between a terminal acetylene and an aryl or vinyl halide in the presence of a copper(I) co-catalyst. This reaction is a powerful tool in the synthesis of various conjugated molecules, including natural products, pharmaceuticals, and functional materials.
Used in the Preparation of 1-Vinyl-4-Phenoxybenzene:
1-Ethynyl-4-phenoxybenzene may be used as a precursor in the preparation of 1-vinyl-4-phenoxybenzene, a compound with potential applications in the synthesis of polymers, pharmaceuticals, and other organic compounds. The conversion from the ethynyl to the vinyl group can be achieved through selective hydrogenation or other chemical transformations, providing access to a broader range of chemical structures and functionalities.

InChI:InChI=1/C9H8S/c1-3-8-4-6-9(10-2)7-5-8/h1,4-7H,2H3

Upstream product

• 17541-02-5 2-Methyl-4-(4-phenoxy-phenyl)-but-3-yn-2-ol 
• 5031-78-7 4-phenoxyacetophenone 
• 871592-08-4 1-(2,2-Dibromo-vinyl)-4-phenoxy-benzene 
• 67-36-7 4-phenoxy benzaldehyde 
• 101-55-3 4-Bromodiphenyl ether 
• 1245913-04-5 trimethyl((4-phenoxyphenyl)ethynyl)silane 
• 52446-51-2 2-(4-phenyloxyphenyl)ethyl alcohol 
• 2974-94-9 4-phenoxyiodobenzene 

Downstream Products

• 17541-21-8 4-[3-(4-phenoxy-phenyl)-prop-2-ynyl]-morpholine 
• 4200-07-1 2-Methyl-6-(4-phenoxy-phenyl)-hexa-3,5-diin-2-ol 
• 4200-17-3 1,4-bis(4-phenoxyphenyl)buta-1,3-diyne 
• 325793-46-2 2-(4-phenoxy-phenylethynyl)-benzothiazole 
• 182196-75-4 1-(4-{4-[2-Oxo-2-(4-phenoxy-phenyl)-acetyl]-benzoyl}-phenyl)-2-(4-phenoxy-phenyl)-ethane-1,2-dione 
• 4200-15-1 <4-Phenoxy-phenyl>-butadiin 
• 4200-20-8 1,8-Bis-<4-phenoxy-phenyl>-octatetrain 
• 17541-22-9 4-[3-(4-phenoxy-phenyl)-propyl]-morpholine 
• 77384-56-6 1,2-bis(4-phenoxyphenyl)ethyne 
• 1094027-54-9 methyl [1-(4-phenoxyphenyl)-1H-benzindene]-3-carboxylate 
• 5031-78-7 4-phenoxyacetophenone 

Relevant academic research and scientific papers

Iron-Catalyzed Tertiary Alkylation of Terminal Alkynes with 1,3-Diesters via a Functionalized Alkyl Radical

Direct oxidative C(sp)?H/C(sp3)?H cross-coupling offers an ideal and environmentally benign protocol for C(sp)?C(sp3) bond formations. As such, reactivity and site-selectivity with respect to C(sp3)?H bond cleavage have remained a persistent challenge. Herein is reported a simple method for iron-catalyzed/silver-mediated tertiary alkylation of terminal alkynes with readily available and versatile 1,3-dicarbonyl compounds. The reaction is suitable for an array of substrates and proceeds in a highly selective manner even employing alkanes containing other tertiary, benzylic, and C(sp3)?H bonds alpha to heteroatoms. Elaboration of the products enables the synthesis of a series of versatile building blocks. Control experiments implicate the in situ generation of a tertiary carbon-centered radical species.

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5-disubstituted isoxazole compounds based on 5-nitrofuran scaffolds

Nineteen 3,5-disubstituted-isoxazole analogs were synthesized based on nitrofuran scaffolds, by a [3 + 2] cycloaddition reaction between terminal acetylenes and 5-nitrofuran chloro-oxime. The compounds were obtained in moderate to very good yields (45–91%). The antileishmanial activity was assayed against the promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. Alkylchlorinated compounds 14p–r were active on both the promastigote and amastigote forms, with emphasis on compound 14p, which showed strong activity against the amastigote form (IC50 = 0.6 μM and selectivity index [SI] = 5.2). In the alkyl series, compound 14o stands out with an IC50 = 8.5 μM and SI = 8.0 on the amastigote form. In the aromatic series, the most active compounds were those containing electron-donor groups, such as trimethoxy isoxazole 14g (IC50 = 1.2 μM and SI = 20.2); compound 14h, with IC50 = 7.0 μM and SI = 6.1; and compound 14j containing the 4-SCH3 group, with IC50 = 5.7 μM and SI = 10.2. In addition, the antifungal activity of 19 nitrofuran isoxazoles was evaluated against five strains of Candida (C. albicans, C. parapsilosis, C. krusei, C. tropicalis, and C. glabrata). Eleven isoxazole derivatives were active against C. parapsilosis, and compound 14o was found to be the most active (minimal inhibitory concentration [MIC] = 3.4 μM) for this strain. Compound 14p was active against all the strains tested, with an MIC = 17.5 μM for C. glabrata, lower than that of the fluconazole used as the reference drug.

Copper-Mediated Deacylative Coupling of Ynones via C-C Bond Activation under Mild Conditions

The intermolecular deacylative coupling of unstrained ynones via C-C bond activation was accomplished by a CuCl-bpy system under mild reaction conditions. This protocol features facile cleavage of the C-C bond at room temperature, broad substrate scope, and efficient construction of important symmetric and unsymmetrical 1,3-diyne adducts through homo or cross coupling of ynones, respectively. The preliminary mechanistic investigations indicated that an acyl copper(III) complex is likely involved in this process.

SO2F2-Mediated Oxidative Dehydrogenation and Dehydration of Alcohols to Alkynes

Direct synthesis of alkynes from inexpensive, abundant alcohols was achieved in high yields (greater than 40 examples, up to 95% yield) through a SO2F2-promoted dehydration and dehydrogenation process. This straightforward transformation of sp3-sp3 (C-C) bonds to sp-sp (C=C) bonds requires only inexpensive and readily available reagents (no transition metals) under mild conditions. The crude alkynes are sufficiently free of impurities to permit direct use in further transformations, as illustrated by regioselective Huisgen alkyne-azide cycloaddition reactions with PhN3 to give 1,4-substituted 1,2,3-traiazoles (16 examples, up to 92% yield) and Sonogashira couplings (10 examples, up to 77% yield).

BTK INHIBITOR

Provided are a series of BTK inhibitors, and specifically disclosed are a compound, pharmaceutically acceptable salt thereof, tautomer thereof or prodrug thereof represented by formula (I), (II), (III) or (IV).

PEST CONTROL AGENT

PROBLEM TO BE SOLVED: To provide a compound having high activity to pest, a pest control agent obtained using the compound and a method for controlling pest by application of the compound. SOLUTION: The present invention provides the pest control agent co

Regio- and stereoselective dimerization of arylacetylenes and optical and electrochemical studies of (E)-1,3-enynes

The N-heterocyclic carbene palladium complex (SIPr)Pd(cinnamyl)Cl [SIPr=N,N'-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene) promotes regio- and stereospecific dimerization of a variety of arylalkynes to give (E)-1,3-enynes in good to excellent yields. An efficient and practical procedure for their synthesis was developed using a biphasic aqueous alkali/heptane system. Optical and electronic properties of (E)-1,3-enynes are highly tunable. Depending on the nature of the substituents, HOMO energies vary in the range 5.3-6.0eV. (E)-1,3-Enynes can exhibit intense photoluminescence in the spectral region 350-500nm.

Synthesis and antiplasmodial activity of new indolone N-Oxide derivatives

A series of 66 new indolone-N-oxide derivatives was synthesized with three different methods. Compounds were evaluated for in vitro activity against CQ-sensitive (3D7), CQ-resistant (FcB1), and CQ and pyrimethamine cross-resistant (K1) strains of Plasmodium falciparum (P.f.), aswell as for cytotoxic concentration (CC50) on MCF7 and KB human tumor cell lines. Compound 26 (5-methoxy-indolone-N-oxide analogue) had the most potent antiplasmodial activity in vitro (50 MCF7/IC50 FcB1: 14623; CC50 KB/IC50 3D7: 198823). In in vivo experiments, compound 1 (dioxymethylene derivatives of the indolone-N-oxide) showed the best antiplasmodial activity against Plasmodium berghei, 62% inhibition of the parasitaemia at 30 mg/kg/day. 2009 American Chemical Society.

Quinoxaline-containing AB2 monomer for hyperbranched aromatic poly(ether-ketones)

A novel AB2 monomer, 2,3-bis(4-phenyloxyphenyl)-6-quinoxaline carboxylic acid.

Synthesis and antimicrobial activity of new 2-phenylethynylbenzothiazoles and related salts

New 2-phenylethynylbenzothiazoles were synthesized by coupling reaction between 2-iodobenzothiazole and substituted phenylacetylenes under palladium catalysis. The modified Wittig reaction was used to prepare the substituted phenylacetylenes from correspo