18398-80-6

Basic information

• Product Name: 2H-Pyran-3-carbonyl chloride, 2-oxo- (8CI,9CI)
• Synonyms: 2H-Pyran-3-carbonyl chloride, 2-oxo- (8CI,9CI);2-oxo-2H-Pyran-3-carbonyl chloride
• CAS NO: 18398-80-6
• Molecular Formula: C₆H₃ClO₃
• Molecular Weight: 158.53922
• Product Categories: ACIDHALIDE
• Mol File: 18398-80-6.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2H-Pyran-3-carbonyl chloride, 2-oxo- (8CI,9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2H-Pyran-3-carbonyl chloride, 2-oxo- (8CI,9CI)(18398-80-6)
• EPA Substance Registry System: 2H-Pyran-3-carbonyl chloride, 2-oxo- (8CI,9CI)(18398-80-6)

Safety Data

• Hazardous Substances Data: 18398-80-6(Hazardous Substances Data)

Upstream product

• 3040-20-8 2-pyrone-3-carboxylic acid 
• 25991-27-9 methyl 2-oxo-2H-pyrane-3-carboxylate 

Downstream Products

• 156301-10-9 (+)-3-carbomenthoxy-2-pyrone 
• 156301-09-6 (-)-3-carbomenthoxy-2-pyrone 
• 127492-00-6 (4R,6S)-4,6-Dihydroxy-cyclohex-1-enecarboxylic acid methyl ester 
• 127492-01-7 chiron 

Relevant articles and documents

2-Fluoroalkyl A-Ring Analogs of 1,25-Dihydroxyvitamin D3. Stereocontrolled Total Synthesis via Intramolecular and Intermolecular Diels-Alder Cycloadditions. Preliminary Biological Testing

Intramolecular Diels-Alder (IMDA) cycloadditions of electron-rich trans-vinylic silaketal groups tethered via a chiral, nonracemic 1,3-butanediol auxiliary to electron-poor 2-pyrone-3-carboxylates (e.g. (R)-9, (S)-14) were promoted by zinc dibromide and proceeded unexpectedly in a stepwise, ionic fashion to form exclusively cis-4,5-disubstituted bicyclic lactones 10 and 15 with nearly complete asymmetric induction.Confirmation of the stereochemical outcome of these nonconcerted IMDA cycloadditions was achieved by 1H NMR spectroscopy and by X-ray crystallography.Fluorinated bicycloadduct (-)-15a was converted smoothly in 13 steps into the lipophilic calcitriol analog 2β-(3'-fluoropropyl)-1β,25-dihydroxyvitamin D3 ((-)5).Intermolecular, concerted, 11 kbar, inverse-electron-demand 4+2-cycloaddition of bis-silylated Z-enol ether 22c, carrying two different silyl groups, with commercial methyl 2-pyrone-3-carboxylate gave in gram amounts only vicinally cis-disubstituted bicycloadduct (+/-)-23c.Chemospecific monodesilylation using sodium azide and then fluorination using Et2NSF3 (DAST) gave fluoroalkyl bicyclic lactone (+/-)-25.This bicyclic lactone (+/-)-25 was transformed into fluorinated, racemic, A-ring phosphine oxide (+/-)-30 that was coupled with enantiomerically pure C,D-ring ketone (+)-21 to form enantiomerically pure diastereomers (-)-4 and (+)-4' as fluorinated, lipophilic, A-ring analogs of 1,25-dihydroxyvitamin D3 (calcitriol).Preliminary biological testing (Table 1) showed that only those diastereomers having the unnatural 1β-hydroxyl group stereochemistry (i.e. (+)-3', (+)-4', and (-)-5 had relatively high affinities for the calf thymus vitamin D receptor and significant antiproliferative and differentiation-inducing potencies in HL-60 cells.

Catalytic asymmetric Diels-Alder reactions of 2-pyrone derivatives

Cycloaddition reactions between the chiral 2-pyrone derivatives 9 and various dienophiles, catalysed by lanthanide shift reagents, afforded diastereomerically pure bicyclic lactones 3. A catalytic asymmetric version of these reactions, using optically act