116805-87-9

Upstream product

• 1070-62-8 5-ethoxy-5-oxopentanoic acid 
• 71-43-2 benzene 
• 2270-20-4 5-Phenylpentanoic acid 
• 35959-54-7 4-hydroxy-4-phenyl-valeric acid 
• 1198-34-1 2-Phenylcyclopentanone 
• 100-52-7 benzaldehyde 
• 114996-07-5 2E-5-hydroxy-5-phenyl-pent-2-enoic acid ethyl ester 
• 1501-05-9 5-oxo-5-phenylvaleric acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 69637-30-5 (+/-)-1-hydroxy-1-phenyl-penten-(3t)-oic acid-⁽⁵⁾ 

Downstream Products

• 10413-17-9 6-phenyltetrahydropyran-2-one 
• 112607-34-8 (6S) 6-phenyltetrahydro-2H-pyran-2-one 
• 112607-33-7 (+)-(R)-δ-(phenyl)-δ-valerolactone 
• 10413-10-2 6-phenyltetrahydro-2H-pyran-2-ol 
• 16015-12-6 3,4-dihydro-2-phenyl-2H-pyran 

Relevant academic research and scientific papers

Visible Light-Driven, Copper-Catalyzed Aerobic Oxidative Cleavage of Cycloalkanones

A visible light-driven, copper-catalyzed aerobic oxidative cleavage of cycloalkanones has been presented. A variety of cycloalkanones with varying ring sizes and various α-substituents reacted well to give the distal keto acids or dicarboxylic acids with moderate to good yields.

Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids

Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.

Copper-Catalyzed Oxidative Cyclization of Carboxylic Acids

A method for converting C-H to C-O bonds through oxidative cyclization of carboxylic acids to generate lactone products is described. The reaction employs catalytic amounts of Cu(OAc)2 and potassium persulfate as the terminal oxidant and is performed open to air in an aqueous acetic acid solvent system. Preliminary mechanistic studies suggest that substrate oxidation likely proceeds by sulfate radical anion and that the Cu catalyst has no influence on the product-determining step. These conclusions differ from related investigations that propose the intermediacy of a carboxylate radical.

NEW CCR2 RECEPTOR ANTAGONISTS AND USES THEREOF

The present invention relates to novel antagonists for CCR2 (CC chemokine receptor 2) and their use for providing medicaments for treating conditions and diseases, especially pulmonary diseases like asthma and COPD.

Organic electrosynthesis using toluates as simple and versatile radical precursors

The electrolysis of toluate esters leads smoothly to the formation of the radical of the alkyl fragment. This property has been used to develop a new electrochemical deoxygenation reaction. The Royal Society of Chemistry.

Substituent dependence of the diastereofacial selectivity in iodination and bromination of glycals and related cyclic enol ethers

The stereochemical course of the electrophilic iodination and bromination of tri-O-benzyl-D-glucal under various conditions has been compared to that of substituted dihydropyrans 2-5. IN3 addition in acetonitrile affords trans-α-iodoazides (80-87%), besides small amounts of trans-β-adducts, in the presence or the absence of benzyloxy substituents at C-3 or C-4, and in agreement with bridged iodonium ion intermediates. In contrast, the diastereofacial selectivity of bromine addition in dichloroethane going through open bromo oxocarbenium ions depends strongly on the substituents. Whereas the trans-α-dibromides are the main (85-95%) adducts in the absence of C-4 and C-5 substituents, in their presence a moderate to exclusive selectivity for cis-α-addition (60-99%) is observed. The predominance of trans-α-addition is again observed whatever the substituents when the bromination is carried out in the same solvent but with a tribromide ion salt, supporting a concerted addition of the two bromine atoms under these conditions. Finally, bromine addition in methanol exhibits a completely different behavior with the nonselective formation of trans-α- and trans-β-methoxybromides and a small dependence on the substituents. In agreement with the absence of azide trapping of any cationic intermediate, it is concluded that these brominations which do not go through an ionic intermediate are concerted additions of bromine and methanol with very loose rate- and product-determining transition states. Finally, the substituent conformation at C-4 influences drastically the stereoselectivity in all these brominations. Evidence for α-anomeric control of the nucleophile approach at C-1 is given by the highly predominant formation of α-adducts, except in the methanolic bromination. The factors determining the versatile selectivity of the electrophile approach are discussed in terms of PPFMO theory and of the special mechanisms of glycal reactions.

Quinones. 4. Novel eicosanoid antagonists: Synthesis and pharmacological evaluation

A new series of ω-phenyl-ω-quinonylalkanoic acids and related compounds was synthesized. The compounds were tested for their inhibitory effects on U-44069-induced contraction of the rabbit aorta. (±)-7-(3,5,6-Trimethyl-1,4-benzoquinon-2-yl)-7-phenylheptanoic acid (4d) (AA-2414) with pA2 value of 8.28 was one of the most potent compounds. Compound 4d inhibited U-46619-induced contraction of the guinea pig lung (pA2 = 8.29) and U-44069-induced aggregation of the guinea pig platelet (IC50 = 3.5 x 10-7 M). Compound 4d displaced the binding of [3H]U-46619 to guinea pig platelets (IC50 = 7.4 x 10-9 M). Compound 4d also showed very potent inhibitory effects with an MED of 0.3 mg/kg (po) on U-46619-, LTD4-, PAF-, or IgG1-induced bronchoconstriction in guinea pigs. The enantiomers of 4d were prepared. The R-(+) isomer 8a was active in both in vitro and in vivo tests, but the S-(-) isomer 8b was much less active. We concluded that the antiasthmatic effects of 4d were based mainly on the TXA2 receptor antagonistic action. In addition, compound 4d showed potent inhibitory effects on PGD2-, PGF(2α)-, and 11-epi-PGF(2α)-induced contraction of the guinea pig tracheal strips. The diverse inhibitory effects might be expressed in terms of eicosanoid-antagonistic activity.