138330-22-0

Upstream product

• 1159707-92-2 2-allyloxy-4-methoxy-1-[1-(4-methoxyphenyl)vinyl]benzene 
• 328314-24-5 4-benzyloxycarbonyl-7-methoxy-4-(4-methoxyphenyl)-2H-1-benzopyran-3(4H)-one 
• 328314-19-8 4-benzyloxycarbonyl-7-methoxy-2H-1-benzopyran-3(4H)-one 
• 328314-09-6 methyl (2-methoxycarbonylmethoxy-4-methoxyphenyl)acetate 
• 328314-10-9 7-methoxy-4-methoxycarbonyl-2H-1-benzopyran-3(4H)-one 
• 212688-07-8 methyl (2-hydroxy-4-methoxyphenyl)acetate 
• 42327-52-6 7-methoxy-chroman-4-one 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 18649-43-9 4-methoxyphenyllead(IV) triacetate 
• 20503-09-7 2-(2-hydroxy-4-methoxyphenyl)acetic acid 

Downstream Products

• 138330-45-7 7-methoxy-4-(4-methoxyphenyl)chroman-3-one 

Relevant academic research and scientific papers

A one-pot three-step synthesis of Z-trisubstituted olefins from arylalkynes and their cyclization into 4-aryl-2H-chromenes

Rapid and versatile access to (Z)-trisubstituted olefins 2 and their cyclization into 4-aryl-2H-chromenes 1 starting fromarylalkynes 3 is described. In a one-pot fashion, alkynes 3 were first hydrated, then transformed into N-tosylhydrazones, and finally

Synthesis and evaluation of the cytotoxicities of neoflavenes

The synthesis of neoflavene and neoflavenes with methoxy substituents at different positions are described. As starting materials, various salicylaldehydes were run through sequential reactions such as O-allylation, Grignard reaction, oxidation, Wittig reaction, and ring-closing metathesis to yield the target neoflavenes in good yield. Among the prepared neoflavenes, 7-methoxy-4′-methoxyneoflavene (6e) and 8-methoxy-4′- methoxyneoflavene (6f) exhibiting potential cell toxicities against various cells were disclosed. In particular, 6f which exhibited an IC50 value of 6.5 ± 2.0 and 5.1 ± 1.1 μM against gastric carcinoma and lung carcinoma cells in vitro was found, respectively. Meanwhile, the structure and activity relationship of our synthesized neoflavenes is further discussed briefly.

Synthesis of neoflavenes by ligand coupling reactions with aryllead triacetates

The reaction of 4-methoxycarbonylchroman-3-one with aryllead triacetates gave the 4-aryl derivatives after 3-4h reaction times in moderate to good yields. Unexpectedly, 2,4-diarylated derivatives were also obtained after longer reaction times. The activating methyl ester group proved difficult to remove by standard decarboxylation procedures. 4-Benzyloxycarbonylchroman-3-ones were therefore prepared and reacted with aryllead triacetates to afford the corresponding 4-aryl derivatives. These were subsequently decarboxylated, reduced and dehydrated to afford neoflavenes in modest overall yields.

Hydroborations: A new convenient route for the preparation of 4-alkyl- (or 4-aryl)chroman-3-ones from 4-alkyl- (or 4-aryl)-2H-chromenes

Hydroboration followed by pyridinium chlorochromate oxidation of 4-alkyl- and 4-aryl-2H-chromenes [4-alkyl- and 4-aryl-(2H)1-benzopyrans] lead to the corresponding 4-substituted chroman-3-ones [4-substituted (2H)-1-benzopyran-3(4H)-ones] in good yields.