88775-71-7

Upstream product

• 88775-25-1 2-(4,5-dibenzyloxy-2-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)-4-oxobutyramide 
• 88775-33-1 2-(4,5-dibenzyloxy-2-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)butyramide 
• 88775-34-2 2-(4,5-dihydroxy-2-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)butyramide 
• 100-44-7 benzyl chloride 
• 88775-31-9 2-(4,5-dibenzyloxy-2-methoxyphenyl)-4-(3,4-methylenedioxyphenyl)butyric acid 

Relevant academic research and scientific papers

BASIC INTRAMOLECULAR ACYLATION. SYNTHESIS OF 2-ARYL-1-TETRALONES BEARING ISOPROPOXY OR BENZYLOXY GROUPS, SYNTHETIC KEY INTERMEDIATES FOR PHENOLIC ANTILEUKAEMIC BENZOPHENANTRIDINE ALKALOIDS, FROM 2,4-DIARILBUTYRIC ACID DERIVATIVES

Generally applicable intramolecular cyclisation of 2,4-diarylbutyric acids having isopropoxy (4) or benzyloxy (12) groups used to protect phenolic functions was required for the purpose of synthesis of phenolic benzophenantridine alkaloids.Treatment of the butyric acids (4b), (4d), (4f), and (12) with POCl3 in acetonitrile in the presence of potassium carbonate furnished the corresponding tetralones (5b), (5d), (5f), and (13) in excellent yield, respectively, without the cleavage of its isopropoxy or benzyloxy groups.A plausible mechanism for basic intramolecular acylation using POCl3 is proposed.

Studies on the chemical constituents of rutaceous plants. L. Development of a versatile method for the synthesis of antitumor-active benzo[c]phenanthridine alkaloids. (2). Preparation of 2-aryl-1-tetralone derivatives

The synthetic pathway from 2,4-bisaryl-4-oxobutyramide (3) to 2-aryl-1-tetralone (4), which is the key intermediate in the Robinson synthesis of antitumor-active benzo[c]phenanthridine alkaloids was improved. Treatment of the model keto-amide (3a) under the reported basic conditions gave γ-keto-α,β-unsaturated acid (9) and degradation products. Reduction of the 2,4-bisaryl-4-oxobutyramide (3) with sodium borohydride gave 2,4-bisaryl-4-hydroxybutyramide (16) which could easily be hydrogenolyzed to give 2,4-bisarylbutyramide (15). However, this transformation also tended to give a γ-lactam derivative (17), unfortunately. We succeeded in the direct hydrogenolysis of the 2,4-bisaryl-4-oxobutyramide (3) to the 2,4-bisarylbutyramide (15), which could be hydrolyzed to the corresponding acid (5) without difficulty. The direct hydrolysis of the 2,4-bisaryl-4-oxobutyronitrile (2) to the 2,4-bisaryl-4-oxobutyric acid (6) as reported by Cheng et al. was also examined. Ten 2-aryl-1-tetralones (4) required as starting materials for syntheses of various benzo[c]phenanthridine alkaloids were prepared.