52903-53-4

Upstream product

• 1191-95-3 cyclobutanone 
• 616-38-6 carbonic acid dimethyl ester 
• 152530-75-1 Methyl 2-<(diphenylmethylene)amino>cyclobutenecarboxylate 

Downstream Products

• 1325642-81-6 methyl 2-oxo-1-(2-oxo-2-phenylethyl)cyclobutanecarboxylate 
• 1501-27-5 Pentanedioic acid, monomethyl ester 
• 141765-13-1 methyl 7-benzyloxy-3-hydroxy-2-methoxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate 
• 141783-88-2 methyl 7-benzyloxy-3-hydroxy-2-methoxy-2,3,3a,4,5,6,7,7a-octahydro-1-benzofuran-4-carboxylate 
• 141765-10-8 methyl 7-benzyloxy-2,2-dimethyl-3a,3b,4,5,6,7,7a,8a-octahydro-dioxolo<4,5-b><1>benzofuran-4-carboxylate 

Relevant academic research and scientific papers

Synthesis of dimethyl glutarate from cyclobutanone and dimethyl carbonate over solid base catalysts

A facile route for the synthesis of dimethyl glutarate (DMG) from cyclobutanone and dimethyl carbonate (DMC) in the presence of solid base catalysts has been developed. It was found that the intermediate carbomethoxycyclobutanone (CMCB) was produced from cyclobutanone with DMC in the first step, and then CMCB was further converted to DMG by reacting with a methoxide group. The role of the basic catalysts can be mainly ascribed to the activation of cyclobutanone via the abstraction of a proton in the α-position by base sites, and solid bases with moderate strength, such as MgO, favor the formation of DMG.

Facile Synthesis of Stable Analogues of 2-Oxocyclobutanecarboxylates: 2-cyclobutanecarboxylates, Derivatives, and Reactions

An efficient two-step synthesis of 2-cyclobutenecarboxylate (4a) and some analogous derivatives from 2-chloro-2-cyclopropylideneacetates 2, 17, 22, and 25 and nonenolizable ketimines, especially diphenylmethyleneamine (DPMA-H), is described.A likely mechanism for the formation of 4a from the primary Michael adduct 3 of DPMA-H to 2 and its substuituted analogues is presented.The unique neighbouring group effect of the DPMA moiety to allow formation of an azaspiropentane intermediate and its regioselective rearrangement to cyclobutenaminederivatives is discussed and further exemplified by an extremely facile SET α-chlorination.Compound 4a and derivatives undergo a thermal ring-opening reaction to the corresponding butadienes with subsequent formation of 1,3-disubstituted 3,4-dihydroisoquinolines 39.Further transformations of 4a and some derivatives include transesterification, hydrolysis to methyl 2-oxocyclobutanecarboxylates, and addition of N-phenyltriazolinedione.