7451-95-8

Usage

InChI:InChI=1/C8H8O2/c9-6-5-7-3-1-2-4-8(7)10/h1-4,6,10H,5H2

Upstream product

• 132637-83-3 [2-((E)-4-Bromo-but-2-enyloxy)-phenyl]-acetaldehyde 
• 91-64-5 coumarin 
• 529-28-2 4-iodoanisol 
• 63600-35-1 2-acetoxystyrene 
• 1745-81-9 o-Allylphenol 
• 90-01-7 salicylic alcohol 

Downstream Products

• 46191-88-2 N-Isopropyl-2-hydroxy-phenyl-ethylamin 
• 60135-72-0 2-amino-4-(2-hydroxyphenyl)thiazole 

Relevant academic research and scientific papers

Immobilized magnetic nano catalyst for oxidation of alcohol

Covalent attachment of Schiff base on magnetic nanoparticles yielded good selectivity for oxidation of alcohols. The ferromagnetic interaction in the complex added comprehensive advantage in enhancing the catalytic activity of the nanocatalyst. A greener approach for alcohol oxidation was achieved in solventless method with good yield (>78%). Leaching experiments confirmed a strong interaction between magnetic support and complex. The catalyst showed significant conversion even after 5 catalytic runs.

Inner workings of a cinchona alkaloid catalyzed oxa-Michael cyclization: Evidence for a concerted hydrogen-bond-network mechanism

Cinchona alkaloids catalyze the oxa-Michael cyclization of 4-(2-hydroxyphenyl)-2-butenoates to benzo-2,3-dihydrofuran-2-yl acetates and related substrates in up to 99 % yield and 91 % ee (ee=enantiomeric excess). Catalyst and substrate variation studies reveal an important role of the alkaloid hydroxy group in the reaction mechanism, but not in the sense of a hydrogen-bonding activation of the carbonyl group of the substrate as assumed by the Hiemstra-Wynberg mechanism of bifunctional catalysis. Deuterium labeling at C-2 of the substrate shows that addition of RO-H to the alkenoate occurs with syn diastereoselectivity of ≥99:1, suggesting a mechanism-based specificity. A concerted hydrogen-bond network mechanism is proposed, in which the alkaloid hydroxy group acts as a general acid in the protonation of the α-carbanionic center of the product enolate. The importance of concerted hydrogen-bond network mechanisms in organocatalytic reactions is discussed. The relative stereochemistry of protonation is proposed as analytical tool for detecting concerted addition mechanisms, as opposed to ionic 1,4-additions. Secret of cyclization: The cinchona alkaloid catalyzed asymmetric oxa-Michael cyclization of 2′-hydroxyphenyl-2-butenoates to benzodihydrofurans proceeds by a highly enantio- and diastereoselective syn-specific addition mode (see scheme). Transition-state activation of the carbonyl group by hydrogen bonding to the catalyst is excluded. This represents a clear-cut demonstration of the importance of concerted hydrogen-bond network mechanisms in cinchona-based asymmetric organocatalysis. Copyright

CYP2A13-catalysed coumarin metabolism: Comparison with CYP2A5 and CYP2A6

1. We investigated the total metabolism of coumarin by baculovirus (BV)-expressed CYP2A13 and compared it with metabolism by BV-expressed CYP2A6. The major coumarin metabolite formed by CYP2A13 was 7-hydroxycoumarin, which accounted for 43% of the total metabolism. The product of 3,4-epoxidation, o-hydroxyphenylacetaldehyde (o-HPA), accounted for 30% of the total metabolites. 2. The Km and Vmax for CYP2A13-mediated coumarin 7-hydroxylation were 0.48 ± 0.07 μM and 0.15 ± 0.006 nmol min-1 nmol-1 CYP, respectively. The Vmax of coumarin 7-hydroxylation by CYP2A13 was about 16-fold lower than that of CYP2A6, whereas the Km was 10-fold lower. 3. In the mouse, there were two orthologues for CYP2A6: CYP2A4 and CYP2A5, which differed by only 11 amino acids. However, CYP2A5 is an efficient coumarin 7-hydroxylase, where as CYP2A4 is not. We report here that BV-expressed CYP2A4 metabolizes coumarin by 3,4-epoxidation. Two products of the 3,4-epoxidation pathway, o-HPA and o-hydroxyphenylacetic acid (o-HPAA), were detected by radioflow HPLC. 4. The Km and Vmax for the coumarin 3,4-epoxidation by CYP2A4 were 8.7 ± 3.6 μM and 0.20 ± 0.04nmol min-1 nmol-1 CYP, respectively. Coumarin 7-hydroxylation by CYP2A5 was more than 200 times more efficient than 3,4 epoxidation by CYP2A4.

Coumarin metabolism by rat esophageal microsomes and cytochrome P450 2A3

The rat esophagus is strikingly sensitive to tumor induction by nitrosamines, and it has been hypothesized that this tissue contains cytochrome P450 enzymes (P450s) which catalyze the metabolic activation of these carcinogens. The metabolic capacity of the esophagus is not well characterized. In the study described here, the products of 14C-coumarin metabolism by rat esophageal microsomes were identified and quantified. Metabolite characterization was by LC/MS/MS and GC/MS and comparison to standards, quantification was by radioflow HPLC. The coumarin metabolites formed by rat esophageal microsomes were compared to those formed by P450 2A3. The major metabolites formed by esophageal microsomes were 8-Hydroxycoumarin, o-Hydroxyphenylacetaldehyde (o-HPA), and o-hydroxyphenylacetic acid (o-HPAA). A smaller amount of 5-hydroxycoumarin, about one-third the 8-hydroxycoumarin, was also formed. o-HPA and o-HPAA are products of coumarin 3,4-epoxidation. The relative rates of coumarin 8-Hydroxylation and 3,4-epoxidation were similar. Coumarin 8-hydroxylation has not previously been reported as a major pathway in any tissue, and no P450s have yet been reported to catalyze this reaction. P450 2A3 catalyzed both the 7-hydroxylation and 3,4-epoxidation of coumarin. P450 2A3 was previously characterized as a coumarin 7-hydroxylase, however, in this study, we report that it catalyzes the formation of o-HPA more efficiently. The Km and Vmax were 1.3 ± 0.35 μM and 0.65 ± 0.06 nmol/min/nmol P450 for coumarin 7-hydroxylation and 1.4 ± 0.58 μM and 3.1 ± 0.46 nmol/min/nmol P450 for o-HPA formation.

HETERO-ATOM SUBSTITUTED CHROMIUM ALLYLS: SYNTHETIC STUDIES ON NEOCARZINOSTATIN CHROMOPHORE ANALOGUES

The preparation and reactions of hetero-atom substituted chromium allyls derived from 7a, 7b, 12, and 15 are described in connection with studies on the synthesis of neocarzinostatin analogues.

New Synthesis of Benzofurans by SRN1 Reaction of ortho-Iodoanisole

Starting from ortho-iodoanisole, 2-substituted benzofurans are obtained in high yield via aromatic nucleophilic radical substitution (SRN1).