63444-54-2

Upstream product

• 1779-49-3 Methyltriphenylphosphonium bromide 
• 39515-51-0 3-Phenoxybenzaldehyde 
• 74-85-1 ethene 
• 58775-83-0 (3-Phenoxyphenyl)acetylene 
• 78427-95-9 1-ethyl-3-phenoxybenzene 
• 80379-89-1 1-(m-phenoxyphenyl)-1-chloroethane 

Downstream Products

• 59908-87-1 2-(3-phenoxy-phenyl)-propionaldehyde 
• 122801-83-6 3-(3-phenoxyphenyl)propanal 
• 1021340-55-5 1-phenoxy-3-[(S)-1-methylallyl]benzene 
• 1021340-54-4 1-phenoxy-3-[1-methylallyl]benzene 
• 1345824-19-2 (S)-N,N'-(1-(3-phenoxyphenyl)ethane-1,2-diyl)bis(N-(methylsulfonyl)methanesulfonamide) 
• 1374869-48-3 N,N'-(1-(3-phenoxyphenyl)ethane-1,2-diyl)bis(N-(methylsulfonyl)methanesulfonamide) 
• 1374869-31-4 N,N'-(1-(3-phenoxyphenyl)ethane-1,2-diyl)bis(4-methyl-N-tosylbenzenesulfonamide) 
• 1640097-13-7 C₂₀H₂₂O 
• 29679-58-1 Fenoprofen 
• 1226783-62-5 (2S)-2-(3-phenoxy-phenyl)-propan-1-ol 

Relevant academic research and scientific papers

Synthesis of 2-Arylpropionaldehydes through Hydroformylation

The rhodium-phospholes and rhodium-phosphanorbornadienes-catalyzed hydroformylation of the readily available vinylarenes 1-3 gives rise to arylpropionaldehydes 4-6 in good yields.

Site-Selective Acceptorless Dehydrogenation of Aliphatics Enabled by Organophotoredox/Cobalt Dual Catalysis

The value of catalytic dehydrogenation of aliphatics (CDA) in organic synthesis has remained largely underexplored. Known homogeneous CDA systems often require the use of sacrificial hydrogen acceptors (or oxidants), precious metal catalysts, and harsh reaction conditions, thus limiting most existing methods to dehydrogenation of non- or low-functionalized alkanes. Here we describe a visible-light-driven, dual-catalyst system consisting of inexpensive organophotoredox and base-metal catalysts for room-temperature, acceptorless-CDA (Al-CDA). Initiated by photoexited 2-chloroanthraquinone, the process involves H atom transfer (HAT) of aliphatics to form alkyl radicals, which then react with cobaloxime to produce olefins and H2. This operationally simple method enables direct dehydrogenation of readily available chemical feedstocks to diversely functionalized olefins. For example, we demonstrate, for the first time, the oxidant-free desaturation of thioethers and amides to alkenyl sulfides and enamides, respectively. Moreover, the system's exceptional site selectivity and functional group tolerance are illustrated by late-stage dehydrogenation and synthesis of 14 biologically relevant molecules and pharmaceutical ingredients. Mechanistic studies have revealed a dual HAT process and provided insights into the origin of reactivity and site selectivity.

Selective Transfer Semihydrogenation of Alkynes with H2O (D2O) as the H (D) Source over a Pd-P Cathode

We reported a selective semihydrogenation (deuteration) of numerous terminal and internal alkynes using H2O (D2O) as the H (D) source over a Pd-P alloy cathode at a lower potential. P-doping caused the enhanced specific adsorption of alkynes and the promoted intrinsic activity for producing adsorbed atomic hydrogen (H*ads) from water electrolysis. The semihydrogenation of alkynes could be accomplished at a lower potential with up to 99 % selectivity and 78 % Faraday efficiency of alkene products, outperforming pure Pd and commercial Pd/C. This electrochemical semihydrogenation of alkynes might proceed via a H*ads addition pathway rather than a proton-coupled electron transfer process. The decreased amount of H*ads at a lower potential and the more preferential adsorption of the Pd-P to C≡C π bond than C=C moiety resulted in the excellent alkene selectivity. This method was capable of producing mono-, di-, and tri-deuterated alkenes with up to 99 % deuterium incorporation.

Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid

Cardanol from cashew nut shell liquid extracted from cashew nut shells was successfully converted into various useful pharmaceutical drugs, such as norfenefrine, rac-phenylephrine, etilefrine and fenoprofene. 3-Vinylphenol, the key intermediate for the synthesis of these drugs, was synthesised from cardanol by ethenolysis to 3-non-8-enylphenol followed by isomerising ethenolysis. The metathesis reaction worked very well using DCM, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. Hydroxyamination of 3-vinylphenol with an iron porphyrin catalyst afforded norfenefrine in over 70% yield. Methylation and ethylation of norfenefrine afforded rac-phenylephrine and etilefrine respectively. A sequence of C-O coupling, isomerising metathesis and selective methoxycarbonylation afforded fenoprofene in good yield. A comparison of the routes described in this paper with some standard literature syntheses of 3-vinylphenol and of the drug molecules shows significant environmental advantages in terms of precursors, yields, number of steps, conditions and the use of catalysts. The Atom Economy of our processes is generally similar or significantly superior to those of the literature processes mainly because the side products produced during synthesis of 3-vinylphenol (1-octeme, 1,4-cyclohexadiene and propene) are easily separable and of commercial value, especially as they are bio-derived. The E Factor for the production of 2-vinylphenol by our process is also very low compared with those of previously reported syntheses.

Catalytic Asymmetric Dearomatization by Visible-Light-Activated [2+2] Photocycloaddition

A novel method for the catalytic asymmetric dearomatization by visible-light-activated [2+2] photocycloaddition with benzofurans and one example of a benzothiophene is reported, thereby providing chiral tricyclic structures with up to four stereocenters including quaternary stereocenters. The benzofurans and the benzothiophene are functionalized at the 2-position with a chelating N-acylpyrazole moiety which permits the coordination of a visible-light-activatable chiral-at-rhodium Lewis acid catalyst. Computational molecular modeling revealed the origin of the unusual regioselectivity and identified the heteroatom in the heterocycle to be key for the regiocontrol.

Structurally Defined Molecular Hypervalent Iodine Catalysts for Intermolecular Enantioselective Reactions

Molecular structures of the most prominent chiral non-racemic hypervalent iodine(III) reagents to date have been elucidated for the first time. The formation of a chirally induced supramolecular scaffold based on a selective hydrogen-bonding arrangement provides an explanation for the consistently high asymmetric induction with these reagents. As an exploratory example, their scope as chiral catalysts was extended to the enantioselective dioxygenation of alkenes. A series of terminal styrenes are converted into the corresponding vicinal diacetoxylation products under mild conditions and provide the proof of principle for a truly intermolecular asymmetric alkene oxidation under iodine(I/III) catalysis.

Oxidative trifluoromethylation and fluoroolefination of unactivated olefins

Fluorine-containing organic compounds are gaining increasing importance in medicinal chemistry. Described herein is a mild and efficient method for the radical addition of olefins with TMSCF3 and TMSCF2R (R = COOEt or CF3) to deliver various α-trifluoromethylated ketones and α-fluoroolefinated ketones.

ISOXAZOLINES AS INHIBITORS OF FATTY ACID AMIDE HYDROLASE

The present invention provides isoxazoline FAAH inhibitors of the formula (I): or pharmaceutically acceptable forms thereof, wherein each of G, Ra, Rb, Rc, and Rd are as defined herein. The present invention also provides pharmaceutical compositions comprising a compound of formula (I), or a pharmaceutically acceptable form thereof, and a pharmaceutically acceptable excipient. The present invention also provides methods for treating an FAAH-mediated condition comprising administering a therapeutically effective amount of a compound of formula (I), or pharmaceutically acceptable form thereof, to a subject in need thereof.

1,2,3-TRIAZOLO[4,5-D]PYRIMIDINES AS P2T RECEPTOR ANTAGONISTS

Compounds of formula having the following stereochemistrywherein R, R1, R2, R3 and R4 are as defined in the specification. The compounds are useful as P2T receptor antagonists