58148-17-7

Upstream product

• 3721-95-7 Cyclobutanecarboxylic acid 
• 58148-13-3 1-butylcyclobutane carboxylic acid 

Downstream Products

• 1610455-54-3 N-(4-cyano-2,3,5,6-tetrafluorophenyl)-1-butylcyclobutanecarboxamide 

Relevant academic research and scientific papers

Pd(II)-Catalyzed Enantioselective C(sp3)-H Borylation

Pd(II)-catalyzed enantioselective borylation of C(sp3)-H bonds has been realized for the first time using chiral acetyl-protected aminomethyl oxazoline ligands. This reaction is compatible with carbocyclic amides containing α-tertiary as well as α-quaternary carbon centers. The chiral β-borylated amides are useful synthons for the synthesis of chiral β-hydroxylated, β-fluorinated, and β-arylated carboxylic acids.

Discovery of highly potent dual EP2and EP3agonists with subtype selectivity

The cyclic carbamate derivatives, 2-{[2-((4S)-4-{(1E,3R)-8-fluoro-3-hydroxy-4,4-dimethyl-1-octenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (5) and 2-{[2-((4S)-4-{(1E,3R)-3-[1-(4-fluorobutyl)cyclobutyl]-3-hydroxy-1-propenyl}-2-oxo-1,3-oxazolidin-3-yl)ethyl]sulfanyl}-1,3-thiazole-4-carboxylic acid (7) were identified as the first potent dual EP2and EP3agonists with selectivity against the EP1and EP4subtypes. Compounds 5 and 7 demonstrated highly potent dual EP2and EP3agonist activity with EC50values of 10 nM or less. In addition, these compounds possess structural features distinct from natural prostaglandins, such as a cyclic carbamate moiety, a dimethyl or cyclobutyl group and a terminal fluorine atom.

Palladium(II)-catalyzed enantioselective C(sp3)-H activation using a chiral hydroxamic acid ligand

An enantioselective method for Pd(II)-catalyzed cross-coupling of methylene β-C(sp3)-H bonds in cyclobutanecarboxylic acid derivatives with arylboron reagents is described. High yields and enantioselectivities were achieved through the development of chiral mono-N-protected α-amino-O- methylhydroxamic acid (MPAHA) ligands, which form a chiral complex with the Pd(II) center. This reaction provides an alternative approach to the enantioselective synthesis of cyclobutanecarboxylates containing α-chiral quaternary stereocenters. This new class of chiral catalysts also show promises for enantioselective β-C(sp3)-H activation of acyclic amides.

15-Cyclobutyl-prostaglandins

Prostaglandin analogues of the formula: STR1 wherein A represents a grouping of the formula: STR2 X represents trans-vinylene or ethylene and Y represents cis-vinylene or ethylene, R represents hydrogen or alkyl of 1 through 12 carbon atoms, R1, R2 and R3 represent hydrogen, or alkyl of 1 through 12 carbon atoms or an aryl group, with the proviso that at least one of the symbols R1, R2 and R3 represents an alkyl or aryl group, are new compounds possessing useful pharmacological properties; they are especially useful for the treatment of gastric ulceration.