51496-26-5

Upstream product

• 106-48-9 4-chloro-phenol 
• 13997-70-1 1-allyloxy-4-chlorobenzene 
• 106-95-6 allyl bromide 
• 13997-73-4 2-allyl-4-chlorophenol 

Downstream Products

• 501368-27-0 7-chloro-2,5-dihydrobenzo[b]oxepine 

Relevant academic research and scientific papers

Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors

In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).

Sequential Two-Fold Claisen Rearrangement, One-Pot Ring-Closing Metathesis and Cross-Metathesis as a Route to Substituted Benzo[b]azepine-2-one, Benzo[b]azepine and Benzo[b]oxepine Derivatives

A synthetic protocol involving sequential use of three atom-economic processes viz. Claisen rearrangement, ring-closing metathesis and cross metathesis has been developed to access 7-substituted benzo[b]azepine and benzo[b]oxepine derivatives starting from appropriate aniline or phenol in good overall yield. A one-pot RCM-CM protocol has also been developed for the synthesis of benzazepine and benzoxepine derivatives.

Chemo- and regioselective reductive transposition of allylic alcohol derivatives via iridium or rhodium catalysis

We report highly chemo- and regioselective reductive transpositions of methyl carbonates to furnish olefin products with complementary regioselectivity to that of established Pd-catalysis. These Rh- and Ir-catalysed transformations proceed under mild conditions and enable selective deoxygenation in the presence of functional groups that are susceptible to reduction by metal hydrides.

A new one-pot synthetic approach to the highly functionalized (Z)-2-(buta-1,3-dienyl)phenols and 2-methyl-2H-chromenes: Use of amine, ruthenium and base-catalysis

A practical and simple one-pot multi-catalysis process for the synthesis of highly substituted benzo[b]oxepines 5, (Z)-2-(buta-1,3-dienyl)phenols 6 and 2-methyl-2H-chromenes 7 from simple starting materials was achieved for the first time through ring-closing metathesis/base-induced ring opening/[1,7]-sigmatropic hydrogen shift reactions. The synthesis of privileged (Z)-2-(buta-1,3-dienyl)phenols 6 via base-induced ring opening of highly functionalized benzo[b]oxepines 5 is described. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

A new synthesis of substituted 2,5-dihydro[b]-oxepines

Based on Claisen rearrangement, Baeyer-Villiger oxidation, and ring-closing metathesis (RCM), a series of substituted 2,5-dihydrobenzo[b]-oxepines were synthesized from isovanillin in good over-all yields. Other appropriate substituted 2,5-dihydrobenzo[b]oxepines prepared from corresponding phenol derivatives were also described.