360774-15-8

Basic information

• Product Name: 3-{3-[6-(Benzyloxy)pyridin-2-yl]-1-hydroxyprop-2-ynyl}-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one
• Synonyms: 3-{3-[6-(Benzyloxy)pyridin-2-yl]-1-hydroxyprop-2-ynyl}-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one
• CAS NO: 360774-15-8
• Molecular Weight: 372.423
• Mol File: 360774-15-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3-{3-[6-(Benzyloxy)pyridin-2-yl]-1-hydroxyprop-2-ynyl}-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-{3-[6-(Benzyloxy)pyridin-2-yl]-1-hydroxyprop-2-ynyl}-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one(360774-15-8)
• EPA Substance Registry System: 3-{3-[6-(Benzyloxy)pyridin-2-yl]-1-hydroxyprop-2-ynyl}-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one(360774-15-8)

Safety Data

• Hazardous Substances Data: 360774-15-8(Hazardous Substances Data)

Upstream product

• 120-92-3 cyclopentanone 
• 108106-97-4 2-oxo-2,5,6,7-tetrahydro-3-cyano-1H-cyclopenta[b]pyridine-3-carbonitrile 
• 134080-69-6 2-ethynyl-6-(phenylmethoxy)pyridine 
• 201274-50-2 2-Oxo-2,5,6,7-tetrahydro-1H-cyclopenta[b]pyridine-3-carboxaldehyde 

Downstream Products

• 201274-52-4 3-{3-[6-(Benzyloxy)pyridin-2-yl]-1-hydroxyprop-2-ynyl}-1-methyl-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one 
• 360774-18-1 3-{3-[6-(Benzyloxy)pyridin-2-yl]-1-[tert-butyl(dimethyl)silyloxy]prop-2-ynyl}-1-methyl-1,5,6,7-tetrahydro-2H-cyclopenta[b]pyridin-2-one 

Relevant articles and documents

Fusicoccin synthesis by intramolecular [4+4] photocycloaddition of 2-pyridones: Stereocontrol of the cycloaddition and elaboration of the pentacyclic product

Intramolecular photocycloaddition of a three-carbon tethered pyrindinone-pyridone system yields the 5-8-5 ring system of the fusicoccin/ophiobolin/ceroplastol families. The stereoselectivity of the cycloaddition was found to be dependent on nitrogen substitution; N-methylation led to exclusively trans products while an absence of nitrogen substitution resulted in solvent-dependent stereoselectivity. Solvent and concentration effects for this cycloaddition were consistent with a hydrogen-bonded dimer that enforces a pro-cis conformation in nonpolar solvents and at higher concentrations. The cis-isomer, a fusicoccin synthesis intermediate, underwent a Cope rearrangement at ambient temperature but could be trapped efficiently as the mono epoxide, yielding a product with six new stereogenic centers. A four-step transformation of an amide carbonyl to a methyl group was achieved using a carbamoyl group to activate the amide for cleavage.