6141-60-2

Usage

InChI:InChI=1/C25H33NO2/c1-21(27)26(19-23-12-8-5-9-13-23)16-14-25(15-17-28-24(2,3)20-25)18-22-10-6-4-7-11-22/h4-13H,14-20H2,1-3H3

Upstream product

• 122889-55-8 spiro<5,6-dicarbomethoxy-4-methyl-7-oxabicyclo<2.2.1>hept-5-en-2-one-3,1'-cyclopropane> 
• 85156-96-3 1-Methyl-7-oxa-bicyclo[2.2.1]hept-2-ene-2,3-dicarboxylic acid dimethyl ester 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 7425-63-0 methyl 3-bromo-2-oxopropanoate 
• 105-45-3 acetoacetic acid methyl ester 

Relevant academic research and scientific papers

Alkali-free, solvent-free conditions through the Feist - Benary reaction process for preparing substituted furyl method (by machine translation)

The present invention provides a process for preparing multi-substituted furyl method, namely in alkali-free, under solvent-free conditions, α - halo with β - dicarbonyl compounds react multi-substituted furyl compound. The invention of the multi-substitu

Traceless solid-phase α-hydroxytropolone synthesis

α-Hydroxytropolones are established inhibitors of several therapeutically relevant binuclear metalloenzymes, and thus lead drug targets for various human diseases. We have leveraged a recently-disclosed three-component oxidopyrylium cycloaddition in the first solid-phase synthesis of α-hydroxytropolones. We also showed that, while minor impurities exist after cleavage and aqueous wash, the semi-crude products display activity in HIV RT-associated RNaseH enzymatic and cell-based assays consistent with pure molecules made in solution phase. These proof-of-principle studies demonstrate the feasibility of solid-phase α-hydroxytropolone synthesis and its potential to serve as a powerful platform for α-hydroxytropolone-based drug discovery and development.

Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo[3.2.1]octa- 3,6-dien-2-ones: Synthesis of methoxytropolones and furans

Methoxytropolones are useful scaffolds for therapeutic development because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo[3.2.1]octa-3,6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R2 = R3 = CO 2Me) instead form furans as the major product.

A mild, convenient and efficient single-step method for the synthesis of polysubstituted furans via ammonium ylide routes

A new and convenient cyclization method for the synthesis of polysubstituted furans in a single-step via ammonium ylide routes was reported. In this process, dimethyl acetylenedicarboxylate reacted with ammonium ylide to produce polysubstituted furan in the presence of anhydrous K2CO 3 at room temperature. It is very economical, environmentally friendly and very easy to carry out. Georg Thieme Verlag Stuttgart.

Studies Dealing with the Excited-State Behavior of Substituted 8-Oxabicyclooct-6-en-2-ones

A series of 8-oxabicyclooct-6-en-2-ones was prepared by the rhodium(II)-catalyzed cyclization-cycloaddition reaction of α-diazopentanedione with various alkynes.The photochemical behavior of these oxabicyclic enones was investigated.Both direct and sensitized photolysis cleanly results in a 1,3-acyl shift.A slower, secondary photoprocess involving intramolecular hydrogen atom transfer and intramolecular cycloaddition of the resulting ketene was also uncovered.The photobehavior of the closely related 9-oxabenzocycloheptene system was also examined.The initially formed 1,3-sigmatropic rearranged product was found to undergo a novel 1,4-methoxyl migration on extended photolysis.The photochemistry of the homologous 7-oxabicyclohepten-2-one was studied.The results obtained can be interpreted in terms of an initial Norrish type I cleavage.The resulting diradical either couples to give the 1,3-acyl shift product or undergoes bond fragmentation, giving products derived from a stepwise retro-Diels-Alder reaction.