82864-22-0

Basic information

• Product Name: (3R,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol
• CAS NO: 82864-22-0
• Molecular Formula: C₁₂H₁₆O₄
• Molecular Weight: 224.253
• Mol File: 82864-22-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 340.6°C at 760 mmHg
• Flash Point: 159.8°C
• Density: 1.22g/cm³
• Vapor Pressure: 3.28E-05mmHg at 25°C
• Refractive Index: 1.557
• CAS DataBase Reference: (3R,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol(82864-22-0)
• EPA Substance Registry System: (3R,4S)-7-methoxy-2,2-dimethyl-3,4-dihydro-2H-chromene-3,4-diol(82864-22-0)

Safety Data

• Hazardous Substances Data: 82864-22-0(Hazardous Substances Data)

Upstream product

• 17598-02-6 2,2 dimethyl 7 methoxychromene 
• 73385-36-1 trans-4-(3-chlorobenzoyloxy)-3-hydroxy-7-methoxy-2,2-dimethylchroman 
• 13229-63-5 trans-3,4-dihydroxy-7-methoxy-2,2-dimethylchroman 
• 180469-89-0 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (3S,4R)-3-bromo-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 180469-90-3 (3S,4R)-3-Bromo-7-methoxy-2,2-dimethyl-chroman-4-ol 
• 73385-38-3 (+/-)-trans-3-Bromo-7-methoxy-2,2-dimethylchraman-4-ol 
• 180469-91-4 (+)-(3R,4R)-3,4-Epoxy-7-methoxy-2,2-dimethylchromane 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3S,4R)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 87894-88-0 (+/-)-3-acetoxy-7-methoxy-2,2-dimethylchroman-4-one 
• 20321-73-7 7-methoxy-2,2-dimethyl-4-chromanone 
• 54874-21-4 7-methoxy-2,2-dimethylchroman-4-ol 
• 343829-23-2 3-Chloro-benzoic acid 3-hydroxy-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 73385-36-1 cis-4-(3-chlorobenzoyloxy)-3-hydroxy-7-methoxy-2,2-dimethylchroman 

Downstream Products

• 82864-23-1 (+)-(3R,4R)-cis-7-Methoxy-2,2-dimethylchromane-3,4-diol 
• 82864-24-2 (-)-(3S,4S)-cis-7-Methoxy-2,2-dimethylchromane-3,4-diol 
• 82864-21-9 (+)-(3S,4R)-trans-7-Methoxy-2,2-dimethylchromane-3,4-diol 
• 83686-04-8 C₃₀H₃₄N₂O₆ 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3R,4S)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3S,4R)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3R,4R)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 82833-91-8 (2-Isopropyl-5-methyl-cyclohexyloxy)-acetic acid (3S,4S)-3-[2-(2-isopropyl-5-methyl-cyclohexyloxy)-acetoxy]-7-methoxy-2,2-dimethyl-chroman-4-yl ester 
• 83686-05-9 C₃₀H₃₄N₂O₆ 

Relevant articles and documents

Efficient one-pot trans-dihydroxylation of 2H-pyrans using dimethyldioxirane (DMD): synthesis of trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin natural products

An efficient one-pot formation of trans-diols on 2H-pyranyl rings was achieved by dimethyldioxirane in wet acetone. This new methodology was applied to the synthesis of natural products containing trans-diol on the pyranyl rings such as trans-3,4-dihydroxy-3,4-dihydro-O-methyloctandreolones, orixalone D, and trans-3,4-dihydroxy-3,4-dihydromollugin.

Chemical and enzyme-catalysed syntheses of enantiopure epoxide and diol derivatives of chromene, 2,2-dimethylchromene, and 7-methoxy-2,2-dimethylchromene (precocene-1)

Procaryotic (bacterial) dioxygenase-catalysed asymmetric dihydroxylation of chromene and 2,2-dimethylchromene to yield the (4S)-enantiomers of the corresponding cis-diols exclusively is reported. The epoxide, and derived cis- and trans-diol products from the previously reported eucaryotic (mammalian) metabolism of precocene-1 (7-methoxy-2,2-dimethylchromene), and the corresponding epoxide and diol derivatives of chromene and 2,2-dimethylchromene, have now been obtained in enantiopure form by chemical resolution of the corresponding bromohydrins using methoxy-(trifluoromethyl)phenylacetic acid (MTPA) or camphanate esters. The absolute configurations of the epoxides, cis- and trans-diols have been determined by chemical synthesis from, and stereochemical correlation with, the corresponding camphanate and MTPA esters. X-Ray crystal structure analysis has provided an unequivocal method for assignment of the absolute stereochemistry in each case.

Studies of Chromens. Part 3. Routes to 2,2-Dimethylchroman-3-ones and 4-Ethyoxycarbonyl-2,2-dimethylchromens. Synthesis of a Stable Chromenopyrazolinone

2,2-Dimethyl-3,4-epoxychroman (6a) was converted into 2,2-dimethylchroman-3-one which readily underwent ethoxycarbonylation to 4-ethoxycarbonyl-2,2-dimethylchroman-3-one (5c).The derived 4-ethoxycarbonyl-2,2-dimethylchromen (1b) reacted with hydrazine to give the pyrazolidinone (4a), oxidation of which gave the stable pyrazolinone (11).Lead tetra-acetate acetoxylation of 7-methoxy-2,2-dimethylchroman-4-one, followed by metal hydride reduction, afforded the 3,4-diols as a mixture of isomers.The relative proportions of cis and trans isomers could be varied from 1:1 to 5:1, respectively, by the choice of reducing conditions.Acid-catalysed dehydration of the diol mixture gave 7-methoxy-2,2-dimethylchroman-3-one (5b).This was unstable and could not be ethoxycarbonylated, but 4-ethoxycarbonyl-7-methoxy-2,2-dimethylchroman-3-one (5d)/(1j) was obtained by a standard synthesis.