496-06-0

Basic information

• Product Name: ipomeanine
• Synonyms: ipomeanine;1-(3-Furanyl)-1,4-pentanedione;1-(3-Furyl)-1,4-pentanedione;1-(3-Furyl)pentane-1,4-dione;Ipomeanin;1-(Furan-3-yl)pentane-1,4-dione
• CAS NO: 496-06-0
• Molecular Formula: C9H10 O3
• Molecular Weight: 166.19
• Mol File: 496-06-0.mol

Chemical Properties

• Melting Point: 42.5°C
• Boiling Point: 234.38°C (rough estimate)
• Flash Point: 127°C
• Appearance: /
• Density: 1.1097 (rough estimate)
• Vapor Pressure: 0.00344mmHg at 25°C
• Refractive Index: 1.4371 (estimate)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: ipomeanine(CAS DataBase Reference)
• NIST Chemistry Reference: ipomeanine(496-06-0)
• EPA Substance Registry System: ipomeanine(496-06-0)

Safety Data

• Hazardous Substances Data: 496-06-0(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 59, p. 4179, 1994 DOI: 10.1021/jo00094a032

InChI:InChI=1/C9H10O3/c1-7(10)2-3-9(11)8-4-5-12-6-8/h4-6H,2-3H2,1H3

Upstream product

• 26214-65-3 furan-3-carbonyl chloride 
• 94806-25-4 (E)-4-(Tri-n-butylstannyl)-3-buten-2-one 
• 84365-18-4 3-<4,4-(ethylenedithio)pentanoyl>furan 
• 247256-65-1 (R)-1-Furan-3-yl-4,8-dimethyl-nonane-1,4,6-triol 
• 84365-24-2 7,7-ethylenedithio-4-oxo-3-(phenylthio)octanal dimethyl acetal 
• 84393-19-1 6,6-Dimethoxy-1-(2-methyl-[1,3]dithiolan-2-yl)-4-phenylsulfanyl-hexan-3-one 
• 84365-21-9 1-<4,4-(ethylenedithio)pentanoyl>aziridine 
• 54717-84-9 3-(2-methyl-[1,3]-dithiolan-2-yl)propionic acid 
• 142896-17-1 (E)-1-(3-Furanyl)-3-(tri-n-butylstannyl)-2-propen-1-one 
• 75-36-5 acetyl chloride 

Relevant articles and documents

THE CONFIGURATION OF THE SESQUITERPENOID 4-HYDROXY-MYOPORONE (ATHANAGRANDIONE)

The conversion of eremoacetal to (-)-1-(furan-3-yl)-4-hydroxy-4,8-dimethylnonane-1,6-dione establishes the configuration of (-)-4-hydroxymyoporone (athanagrandione) as R.Key words: Ipomoea batatas; Convolvulaceae; FUsarium solani; Athanasia grandiceps; sweet potato; sesquiterpenoid; configuration; 4-hydroxymyoporone; athanagrandione; eremoacetal.

Synthesis of 3-Acylfurans Using 3-(Phenylthio)propanal Dimethyl Acetal as a New Synthon. Syntheses of Ipomeanine and Isoegomaketone

It was found that 3-(phenylthio)propanal dimethyl acetal is a very useful starting material for the preparation of 3-acylfuranoterpenes.Syntheses of two naturally-occurring furans, isoegomaketone and ipomeanine were described.

Palladium-Catalyzed Reductive Coupling of Acid Chlorides with β-Stannyl Enones: Synthesis of 1,4-Diketones and Mechanistic Aspects

The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl intermediate.The double bond conjugated with a single carbonyl group was not significantly reduced.The generality of the method is illustrated by two syntheses of the 1,4-diketone ipomeanine.By performing the reaction at lower temperatures, α,β-unsaturated 1,4-diketones can also be prepared.The reduction of the intermediate α,β-unsaturated 1,4-diketones probably proceeds by insertion of a palladium hydride, formed in situ by reaction of a Pd(II) complex with Bu3SnCl, followed by hydrolysis of the intermediate palladium enolate.

Synthesis of 1,4-Diketones by Palladium-Catalyzed Reductive Coupling of Acid Chlorides with (E)-1,2-Bis(tri-n-butylstannyl)ethene or β-Stannyl Enones

The palladium-catalyzed coupling of acid chlorides with (E)-1,2-bis(tri-n-butylstannyl)ethene or β-stannyl enones gives butane-1,4-diones directly by reduction of the intermediate enedicarbonyl derivative by a palladium hydride derived from n-Bu3SnCl.