4439-62-7

Basic information

• Product Name: rotenonone
• Synonyms: rotenonone;(2R)-1,2-Dihydro-2α-isopropenyl-8,9-dimethoxy-[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6,12-dione;(R)-1,2-Dihydro-8,9-dimethoxy-2-(1-methylethenyl)[1]benzopyrano[3,4-b]furo[2,3-h][1]benzopyran-6,12-dione
• CAS NO: 4439-62-7
• Molecular Formula: C₂₃H₁₈O₇
• Molecular Weight: 406.38482
• Mol File: 4439-62-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 615.6°C at 760 mmHg
• Flash Point: 269.2°C
• Appearance: /
• Density: 1.43g/cm³
• Vapor Pressure: 4.37E-15mmHg at 25°C
• Refractive Index: 1.655
• CAS DataBase Reference: rotenonone(CAS DataBase Reference)
• NIST Chemistry Reference: rotenonone(4439-62-7)
• EPA Substance Registry System: rotenonone(4439-62-7)

Safety Data

• Hazardous Substances Data: 4439-62-7(Hazardous Substances Data)

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

• 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 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 83-79-4 rotenone 
• 116513-52-1 rotenononic acid 
• 116513-53-2 methyl rotenononate 
• 116513-54-3 β-rotenonone 
• 3276-13-9 Derritol 
• 95-92-1 oxalic acid diethyl ester 
• 4755-77-5 Ethyl oxalyl chloride 

Downstream Products

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

Relevant articles and documents

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).

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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.