74185-15-2

Upstream product

• 52244-70-9 4-(4-methoxyphenyl)butan-1-ol 
• 100-66-3 methoxybenzene 
• 74893-19-9 4,4,6-trimethyl-2-(2-p-methoxyphenylethyl)-5,6-dihydro-4H-1,3-oxazine 
• 824-94-2 p-methoxybenzyl chloride 
• 88537-45-5 4-Methylphenylsulfonic acid 4-(4-methoxyphenyl)butyl ester 
• 35191-43-6 1-(4-bromo-butyl)-4-methoxy-benzene 
• 74174-19-9 4-Methoxy-2-oxa-tricyclo[13.2.2.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaen-10-ol 
• 74174-17-7 acerogenin B 
• 74174-18-8 4-Methoxy-10-(tetrahydro-pyran-2-yloxy)-2-oxa-tricyclo[13.2.2.1^3,7]icosa-1⁽¹⁸⁾,3,5,7⁽²⁰⁾,15⁽¹⁹⁾,16-hexaene 
• 832-01-9 methyl p-methoxycinnamate 
• 3153-44-4 4-(4-methoxy-phenyl)-4-oxo-butyric acid 
• 830-09-1 3-(4'-methoxyphenyl)propenoic acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 20637-08-5 4-(4-methoxyphenyl)butyric acid methyl ester 

Downstream Products

• 88537-40-0 Acetic acid 5-(4-methoxy-phenyl)-1-[2-(4-methoxy-phenyl)-ethyl]-pentyl ester 
• 88537-41-1 1,7-bis(3-iodo-4-methoxyphenyl)heptan-3-yl acetate 

Relevant academic research and scientific papers

A facile synthesis of di-O-methyl centrolobol

A facile route to (±)di-O-methyl centrolobol 4 has been explored starting from 4-oxo-4-(4-methoxyphenyl) butanoic acid 7 and 4-methoxycinnamic acid 13.

Synthesis of meta,meta-Bridged Biaryls (-Metacyclophanes) via Aryl-Aryl Coupling: Factors affecting the Cyclisation

Two bis(iodoaryl)heptanoids (28) and (33), the iodoarylbutyl iodoarylpropyl sulphide (39), and the corresponding sulphone (40) have been prepared, and each treated with tetrakis(triphenylphosphine)nikel(0).Two new m,m-bridged biaryls (29) (31percent) and (34) (49percent) were obtained; the sulphur compounds were deiodinated in preference to coupling.These reactions are compared with those used previously in myricanol synthesis and the factors affecting ring closure are discussed.Steric effects at the coupling sites appear more important in determining product yield than torsional strain in the products.

Methods for the Construction of Linear 1,7-Diarylheptanoids; Synthesis of Di-O-methylcentrolobol and Precursors (Synthetic and Biosynthetic) to the meta,meta-Bridged Biphenyls Myricanol and Myricanone

1,7-diarylheptanoids are a varied natural product class in which 'linear' types appear to be biosynthetic precursors to macro(carbo)cyclic (3), macro(oxa)cyclic (4), and condensed polycyclic (5) examples.Various methods (suitable for radiolabelling) are described for constructing 'linear' diarylheptanoids, including Grignard couplings (employing activated magnesium) with arylpropanals and oxazonium salts (11a), (11h), (15a), and (15b)> and dithian alkylation (15c)>.Alkyl-lithium treatment of the benzyloxydithian (19b) gave 1,2,3-triphenylcyclopropane.Syntheses via trialkylcyanoborates were frustrated by disproportionation of the intermediate trialkylboranes.The diarylheptanoids synthesised (11a-h) and (15a-e) include synthetic and biosynthetic precursors to meta,meta-bridged biphenyls and related macrocyclic ethers.

Studies on the Constituents of Aceraceae Plants. III. Structure of Acerogenin B from Acer nikoense MAXIM.

Acerogenin B (3), C19H22O3, mp 179 deg C, D23 +/-0 deg, a new diarylheptanoid of diphenyl ether type, was isolated from an acid hydrolysate of the glycoside mixture extracted from the bark of Acer nikoense MAXIM.The structure of acerogenin B (3) was established as formula 3 in Chart 1 on the basis of the spectral data and chemical correlation with acerogenin A (2).Acerogenin B (3) was considered to be a racemic compound in view of the optical inactivity of 3 and its derivatives (4 and 10).Keywords - Acer nikoense; Aceraceae; acerogenin B; diarylheptanoid; diphenyl ether; 1H- and 13C-NMR