85616-39-3

Upstream product

• 932-31-0 ortho-tolylmagnesium bromide 
• 1490-25-1 succinic acid monomethylester chloride 
• 67-56-1 methanol 
• 6939-36-2 4-(2-methylphenyl)-4-oxobutanoic acid 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 85616-40-6 4-methoxycarbonylmethyl-4-(o-tolyl)-4-butanolide 
• 87-41-2 2-benzofuran-1(3H)-one 
• 1210050-43-3 C₁₂H₁₂O₄ 
• 1210050-48-8 C₁₄H₁₆O₅ 
• 1360804-77-8 methyl 3-[2-(2-methylphenyl)-1,3-dioxolan-2-yl]propanoate 
• 1360804-80-3 tert-butyl 5-[1-(3-(2-o-tolyl-1,3-dioxolan-2-yl)propyl)piperidin-4-yl]pentylcarbamate 
• 1360804-79-0 3-[2-(2-methylphenyl)]-1,3-dioxolan-2-propyl methylsulfonate 
• 1360804-78-9 3-[2-(2-methylphenyl)-1,3-dioxolan-2-yl]propanol 
• 85616-41-7 4-o-tolyl-5-methoxycarbonylpentanoic acid 
• 6939-36-2 4-(2-methylphenyl)-4-oxobutanoic acid 

Relevant academic research and scientific papers

Fluorescent derivatives of AC-42 to probe bitopic orthosteric/allosteric binding mechanisms on muscarinic M1 receptors

Two fluorescent derivatives of the M1 muscarinic selective agonist AC-42 were synthesized by coupling the lissamine rhodamine B fluorophore (in ortho and para positions) to AC42-NH2. This precursor, prepared according to an original seven-step procedure, was included in the study together with the LRB fluorophore (alone or linked to an alkyl chain). All these compounds are antagonists, but examination of their ability to inhibit or modulate orthosteric [3H]NMS binding revealed that para-LRB-AC42 shared several properties with AC-42. Carefully designed experiments allowed para-LRB-AC42 to be used as a FRET tracer on EGFP-fused M1 receptors. Under equilibrium binding conditions, orthosteric ligands, AC-42, and the allosteric modulator gallamine behaved as competitors of para-LRB-AC42 binding whereas other allosteric compounds such as WIN 51,708 and N-desmethylclozapine were noncompetitive inhibitors. Finally, molecular modeling studies focused on putative orthosteric/allosteric bitopic poses for AC-42 and para-LRB-AC42 in a 3D model of the human M1 receptor.

Effect of alkyl substituents on photorelease from butyrophenone derivatives

"Chemical Equation Presented" Photolysis of la yields 4a in argon-saturated methanol, whereas 1b is photostable. Laser flash photolysis of 1a in acetonitrile shows formation of biradical 2a (λmax = 340 nm, τ = ～60 ns), which undergoes intersystem crossing to form Z-3a (λmax = 380 nm, τ = 270 ns) and E-3a (λ max = 380 nm, τ = 300 ms). Z-3a regenerates the starting material, whereas E-3b undergoes intramolecular lactonization to release the alcohol moiety and form 4a. Similar laser flash photolysis of lb shows formation of biradical 2b (λmax = 340 nm, τ = 1.9 μs in acetonitrile), which is longer-lived than 2a is. However, 2b only undergoes intersystem crossing to form Z-3b (λmax = 380 nm, τ = 4.3 μs). Calculations demonstrate that intramolecular pseudo hydrogen bonding between the OH moiety and the radical centered on the isopropyl carbon in 2b and the bulkiness of the isopropyl group prevent the necessary rotation to form E-3b. In comparison, 2a does not form an intramolecular pseudo hydrogen bond between the methylene radical center and the OH group, and as a consequence, it undergoes intersystem crossing to form both E- and Z-3a.

Generation of Acyl Radicals from 1-Oxidoalkylidenechromium(0) Complexes by Treatment with Bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II) and Their Reactions with Olefins

Tetramethylammonium pentacarbonyl(1-oxidoalkylidene)chromium(0) complexes are oxidized with bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II) to generate acyl radicals which react electron-deficient olefins, giving intermolecular addition products.