170235-79-7

Upstream product

• 164921-74-8 methyl 4-(2'-methoxy-4'-methylphenyl)-5-hydroxy-(2E)-pentanoate 

Downstream Products

• 155608-76-7 Toluene-4-sulfonic acid 4-(2-methoxy-4-methyl-phenyl)-pentyl ester 
• 122427-49-0 5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid 
• 170235-86-6 4-(2'-methoxymethyloxy-4'-methylphenyl)pentyl acetate 
• 170235-89-9 4-(1,5-dimethyl-4-hexenyl)-3-(methoxymethoxy)toluene 
• 170235-88-8 4-(2-Methoxymethoxy-4-methyl-phenyl)-pentanal 
• 170235-84-4 4-(2'-methoxy-4'-methylphenyl)pentyl acetate 
• 170235-85-5 4-(2'-hydroxy-4'-methylphenyl)pentyl acetate 
• 170235-87-7 4-(2'-methoxymethyloxy-4'-methylphenyl)pentanol 
• 170235-81-1 1-iodo-4-(2'-methoxy-4'-methylphenyl)pentane 
• 170235-99-1 2,5-bis(methoxymethoxy)-4-(1,5-dimethylhex-4-enyl)toluene 
• 170235-98-0 4-(2,5-Bis-methoxymethoxy-4-methyl-phenyl)-pentanal 
• 170235-83-3 methyl-5-(2'-hydroxy-4'-methylphenyl)hexanoate 
• 122427-48-9 4-(2'-methoxy-4'-methylphenyl)hexanenitrile 
• 78964-27-9 (+/-)-curcuhydroquinone 

Relevant academic research and scientific papers

Reaction of methyl 4,5-epoxy-(2E)-pentenoate with arenes. II. Application to the synthesis of(±)-curcudiol, (±)-curcuphenol, (±)-curcuhydroquinone, and(±)-curcuquinone

Four bisabolane sesquiterpenes, (±)-curcudiol (2), (±)-curcuphenol (3), (±)-curcuhydroquinone (5) and (±)-curcuquinone (6), were synthesized based on the reaction of methyl 4,5-epoxy-(2E)-pentenoate (1) with methoxytoluenes in the presence of boron trifluoride etherate.

Intramolecular reaction of a phenonium ion. Novel lactonization of 4-aryl-5-tosyloxypentanoates and 4-aryl-5-tosyloxyhexanoates concomitant with a phenyl rearrangement

The novel lactonizations of methyl 4-aryl-5-tosyloxypentanoate 1 and 4-aryl-5-tosyloxyhexanoate 3 concomitant with a phenyl rearrangement are reported. The lactonizations were promoted by silica gel or heating in various solvents. By examining the effects of substituents of the aromatic ring on the reactivity, it was found that the reaction proceeded via a phenonium ion. This finding was supported by the stereochemical results for the lactonization of optical active 1. Silica gel-promoted lactonization of 1 gave only γ-lactone 2, whereas that of 3 afforded γ-lactone 4 and δ-lactone 5. These lactonizations proved to be kinetically controlled. On the other hand, when 3c was heated in CH3NO2 at 70°C, the highly selective formation of 4c was observed. Further detailed experiments confirmed that the thermal lactonization in CH3NO2 was thermodynamically controlled.

A FACILE SYNTHESIS OF 4-ARYL-5-HYDROXY-(2E)-PENTENOATE DERIVATIVES AND ITS APPLICATIONS TO THE FIRST SYNTHESIS OF (+/-)-CURUCUDIOL, (+/-)-CURCUHYDROQUINONE AND (+/-)-CURCUQUINONE

The first syntheses of three kinds of bisabolane sesquiterpenes, (+/-)-curcudiol (29), (+/-)-curcuhydroquinone (40) and (+/-)-curcuquinone (41) were achieved based on the BF3*Et2O catalyzed reaction of (+/-) methyl 4,5-epoxy-(2E)-pentenoate (1) and polyme