21148-31-2

Usage

InChI:InChI=1/C16H16O2/c1-18-16-12-15(17)11-10-14(16)9-5-8-13-6-3-2-4-7-13/h2-8,10-12,17H,9H2,1H3/b8-5+

Upstream product

• 69470-84-4 (E)-1-(4-hydroxy-2-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 150-19-6 O-methylresorcine 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 493-33-4 1-(4-hydroxy-2-methoxy-phenyl)ethanone 
• 100-52-7 benzaldehyde 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 21040-45-9 Cinnamyl acetate 

Downstream Products

• 69470-81-1 (E)-1-phenyl-3-(2,4-dimethoxyphenyl)-1-propene 

Relevant academic research and scientific papers

[Pd]-Catalyzedpara-selective allylation of phenols: access to 4-[(E)-3-aryl/alkylprop-2-enyl]phenols

4-[(E)-3-Arylprop-2-enyl]phenols are omnipresent scaffolds and constitute natural products and biologically significant compounds. Obtusastyrene and obtustyrene are two such phenolic-based natural products isolated fromDalbergia retusa. The development of strategies based on a site-selective allylation, particularly protecting group-free substrates and non-activated coupling agents, is indispensable in organic synthesis. Herein, we present a highly regioselective [Pd]-catalyzedpara-allylation of phenols using simple, inactivated allylic alcohols as allylating coupling partners. Notably, this strategy is successful in open-air and under mild reaction conditions. Besides, the efficacy of the present protocol was demonstrated by the direct synthesis of obtusastyrene and obtustyrene.

Synthetic cinnamylphenol derivatives as cancer chemopreventive agents

Several substituted cinnamylphenol (1,3-diphenylpropene) derivatives were synthesized and tested for their inhibitory activities against in vitro Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol-13-acetate in Raji cells. The prenylated cinnamylphenols were found to show remarkably potent activity. Furthermore, prenylated cinnamylphenols (19 and 25) exhibited a marked inhibitory effect on mouse skin tumor promotion in an in vivo two-stage carcinogenesis test. These results indicate that some prenylated cinnamylphenols might be valuable as potential cancer chemopreventive agents (anti-tumor promoters).

A convenient and improved montmorillonite K-10 catalysed Friedel-Crafts benzylation and allylation with activated esters

Benzyl benzoate and cinnamyl acetate has been effectively used respectively as alkylating and allylating substrates in Friedel-Crafts reaction catalysed by montmorillonite K-10 clay.

Inhibitors of prostaglandin biosynthesis from Dalbergia odorifera

The root heartwood of Dalbergia odorifera T. CHEN (Leguminosae) is a Chinese medicinal drug (Japanese name koshinko) used for a stagnant blood syndrome (stagnation of disordered blood; Japanese, oketsu). In addition to 10 known compounds, five new phenolic compounds, isomucronustyrene and hydroxyobtustyrene (cinnamylphenols), (+)-isoduartin (isoflavan), odoriflavene (isoflav-3-ene) and (-)-odoricarpan (pterocarpan) were isolated and their structures were elucidated on the basis of chemical and spectroseopic methods. Of the fifteen compounds isolated, cinnamylphenols, isoflavans, isoflavene and benzoic acid derivative significantly inhibited prostaglandin biosynthesis as well as platelet aggregation induced by arachidonic acid.

FLAVONOID AND OTHER CONSTITUENTS OF BAUHINIA MANCA

Phytochemical analysis of the stem of Bauhinia manca yielded 63 compounds, among them six new natural products.Major constituents were found to be 3-O-galloylepicatechin, gallic acid, cinnamic acid, β-sitosterol and its β-D-glucoside.The two new flavans possess significant antifungal activity.Key Word Index-Bauhinia manca; Leguminosae; 5,5-dimethoxylariciresinol; 4-O-methylisoliquiritigenin; 4'-O-methylliquiritigenin; 7,3'-dimethoxy-4-hydroxyflavan; 3',4'-dihydroxy-7-methoxyflavan; 2,4'-dihydroxy-4-methoxydihydrochalcone; antimicrobial activity.

A VERSATILE TOTAL SYNTHESIS OF XENOGNOSIN

Xenognosin, 4, the first identified host recognition substance for parasitic angiosperms has been synthesized by a route efficient for the preparation of several structural analoques.