4439-62-7

Usage

InChI:InChI=1/C23H18O7/c1-10(2)15-8-13-14(28-15)6-5-11-20(24)19-12-7-17(26-3)18(27-4)9-16(12)29-23(25)22(19)30-21(11)13/h5-7,9,15H,1,8H2,2-4H3/t15-/m1/s1

Upstream product

• 3276-13-9 Derritol 
• 4755-77-5 Ethyl oxalyl chloride 
• 95-92-1 oxalic acid diethyl ester 
• 116513-54-3 β-rotenonone 
• 116513-53-2 methyl rotenononate 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 108-46-3 recorcinol 
• 500865-17-8 ethyl 3-(3,4-dimethoxyphenyl)-7-hydroxy-4-oxo-4H-chromene-2-carboxylate 
• 24126-98-5 1-(2,4-dihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethan-1-one 
• 83-79-4 rotenone 
• 116513-52-1 rotenononic acid 

Downstream Products

• 3276-13-9 Derritol 
• 144-62-7 oxalic acid 

Relevant academic research and scientific papers

STUDIES ON THE CHEMICAL TRANSFORMATIONS OF ROTENOIDS. III. RING CONVERSIONS OF METHYL ROTENONONATE AND β-ROTENONONE

Ring conversions of methyl rotenononate (2b) and β-rotenonone (3) into rotenonone (1) or 4H-furobenzopyrans (5a-b) were investigated.The Beckmann rearrangement of 2b oxime (6) in PPA provided methyl 3-(benzofuran-5-yl)carbonylamino- (9), 3-(benzofuran-5-yl)aminocarbonyl-2-benzofurancarboxylate (10) and furobenzoxazole (11), whereas 3 oxime (12) gave furo benzoxazole (13) as a single product.Compound 2b underwent ring closure with hydrazines to provide benzofuropyridazin-4(3H)-ones (14a-e).

A Concise Approach to Oxo-Dehydrorotenoid by Direct Lactonization and the Total Syntheses of Stemonone, Rotenonone, 6-Oxo-dehydroelliptone, and 6-Oxo-6a,12a-dehydrodeguelin

An approach to construct the oxo-dehydrorotenoids via direct lactonization of isoflavone-2-carboxylic acids is reported. The present reaction proceeds smoothly with good substrate scope and an operationally simple protocol. The application of this method

STUDIES ON THE CHEMICAL TRANSFORMATION OF ROTENOIDS. II. REACTIONS OF ROTENONE AND ROTENONONE WITH PRIMARY AMINES

The ring transformations of rotenone and rotenonone by primary amines were investigated.The improved synthetic methods for rotenonone were also developed.Rotenone (1) underwent cleavage of C-12a and O-13 linkage to give alkylamines (2a-b), while rotenonone (5) gave 2-alkylcarbamoyl-4-alkylimino-8-methylethenyl-3-(2-hydroxy-4,5-dimethoxy)phenyl-8,9-dihydro-4H-furobenzopyrans (7a-d) as a result of nucleophilic attack on C-12 carbon.Compound 1 was oxidized bynitrosyl chloride or dimethyl sulfoxide in the presence of iodine and sulfuric acid to provide rotenonone (5) in improved yields respectively.