13732-85-9

Upstream product

• 13633-20-0 2-Hydroxy-2-methyl-6-phenyl-hexadien-(3,4) 
• 20620-59-1 5-phenyl-n-valeric acid methyl ester 
• 75-16-1 methylmagnesium bromide 
• 768-56-9 4-Phenylbut-1-ene 
• 67-64-1 acetone 
• 10521-91-2 5-phenylpentan-1-ol 
• 917-54-4 methyllithium 
• 2270-20-4 5-Phenylpentanoic acid 
• 103-63-9 1-phenyl-2-bromoethane 
• 3360-41-6 4-phenyl-butan-1-ol 
• 591-51-5 phenyllithium 
• 690-94-8 dimethyl(vinylethynyl)carbinol 
• 79889-19-3 2-methyl-6-phenyl-2-hexyl hydroperoxide 
• 13633-25-5 1-Bromo-4-phenylbutane 

Downstream Products

• 36748-60-4 1-Isopropyltetralin 
• 1439367-55-1 1,1-dimethyl-5-phenylpentyl-1-yl pyridin-2-yl carbonate 
• 1439367-56-2 (1,1-dimethyl-5-phenyl-pentyl) 2-oxopyridine-1-carboxylate 
• 1439366-75-2 (1,1-dimethyl-5-phenyl-pentyl) N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]-carbamate 
• 97847-89-7 (1,1-dimethyl-5-phenyl-pentyl)-amine hydrochloride 
• 1430423-76-9 C₁₂H₁₇FO 
• 79889-26-2 3,3-Dimethyl-7-phenyl-[1,2]dioxepane 
• 79889-19-3 2-methyl-6-phenyl-2-hexyl hydroperoxide 

Relevant academic research and scientific papers

An Iron-Mesoionic Carbene Complex for Catalytic Intramolecular C-H Amination Utilizing Organic Azides

The synthesis of N-heterocycles is of paramount importance for the pharmaceutical industry. They are often synthesized through atom economic and environmentally unfriendly methods, generating significant waste. A less explored, but greener, alternative is

Electroreductive Olefin-Ketone Coupling

A user-friendly approach is presented to sidestep the venerable Grignard addition to unactivated ketones to access tertiary alcohols by reversing the polarity of the disconnection. In this work a ketone instead acts as a nucleophile when adding to simple unactivated olefins to accomplish the same overall transformation. The scope of this coupling is broad as enabled using an electrochemical approach, and the reaction is scalable, chemoselective, and requires no precaution to exclude air or water. Multiple applications demonstrate the simplifying nature of the reaction on multistep synthesis, and mechanistic studies point to an intuitive mechanism reminiscent of other chemical reductants such as SmI2 (which cannot accomplish the same reaction).

SUBSTITUTED BENZOXAZOLONE DERIVATIVES AS ACID CERAMIDASE INHIBITORS, AND THEIR USE AS MEDICAMENTS

The present invention relates to substituted benzoxazolone derivatives as acid ceramidase inhibitors, pharmaceutical compositions containing these inhibitors and methods of inhibiting acid ceramidase for the treatment of disorders in which modulation of the levels of ceramide is clinically relevant. The invention also provides substituted benzoxazolone derivatives for use in the treatment of cancer, inflammation, pain, inflammatory pain or pulmonary diseases.

Synthesis and structure-activity relationship (SAR) of 2-methyl-4-oxo-3- oxetanylcarbamic acid esters, a class of potent N-acylethanolamine acid amidase (NAAA) inhibitors

N-Acylethanolamine acid amidase (NAAA) is a lysosomal cysteine hydrolase involved in the degradation of saturated and monounsaturated fatty acid ethanolamides (FAEs), a family of endogenous lipid agonists of peroxisome proliferator-activated receptor-α, which include oleoylethanolamide (OEA) and palmitoylethanolamide (PEA). The β-lactone derivatives (S)-N-(2-oxo-3-oxetanyl)-3-phenylpropionamide (2) and (S)-N-(2-oxo-3-oxetanyl)- biphenyl-4-carboxamide (3) inhibit NAAA, prevent FAE hydrolysis in activated inflammatory cells, and reduce tissue reactions to pro-inflammatory stimuli. Recently, our group disclosed ARN077 (4), a potent NAAA inhibitor that is active in vivo by topical administration in rodent models of hyperalgesia and allodynia. In the present study, we investigated the structure-activity relationship (SAR) of threonine-derived β-lactone analogues of compound 4. The main results of this work were an enhancement of the inhibitory potency of β-lactone carbamate derivatives for NAAA and the identification of (4-phenylphenyl)-methyl-N-[(2S,3R)-2-methyl-4-oxo-oxetan-3-yl]carbamate (14q) as the first single-digit nanomolar inhibitor of intracellular NAAA activity (IC50 = 7 nM on both rat NAAA and human NAAA).

The reaction of alkyl peroxy radicals

Secondary alkyl peroxy radicals generated from 4-phenyl-2-butyl-, 2-nonyl- and 3α-cholestanyl hydroperoxides at 45°C undergo Russell termination reactions in preference to non-terminating decomposition reactions. Non-terminating decomposition of 2-nonyl peroxy radicals afforded 2,5-nonanedione and 2,5-nonanediol due to intramolecular hydrogen abstraction reactions of alkoxy radicals. The radicals derived from 2-methyl-4-phenyl-2-butyl-, 2-methyl-5-phenyl-2-pentyl- and 2-methyl-6-phenyl-2-hexyl hydroperoxides afforded benzylic functionalized products due to intermolecular reactions. 2-Hexylperoxy radicals generated in excess alcohols ineffectively abstracted the α-hydrogens of alcohols. These results demonstrate the low reactivity of alkyl peroxy radicals.