26057-70-5

Basic information

• Product Name: Furo(3,4-b)furan-2,6(3H,4H)-dione, dihydro-3-methylene-4-octyl-, (+-)-
• Synonyms: Furo(3,4-b)furan-2,6(3H,4H)-dione, dihydro-3-methylene-4-octyl-, (+-)-
• CAS NO: 26057-70-5
• Molecular Formula: C15H22 O4
• Molecular Weight: 266.33
• Mol File: 26057-70-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 458.2°Cat760mmHg
• Flash Point: 235.3°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 1.4E-08mmHg at 25°C
• Refractive Index: 1.495
• CAS DataBase Reference: Furo(3,4-b)furan-2,6(3H,4H)-dione, dihydro-3-methylene-4-octyl-, (+-)-(CAS DataBase Reference)
• NIST Chemistry Reference: Furo(3,4-b)furan-2,6(3H,4H)-dione, dihydro-3-methylene-4-octyl-, (+-)-(26057-70-5)
• EPA Substance Registry System: Furo(3,4-b)furan-2,6(3H,4H)-dione, dihydro-3-methylene-4-octyl-, (+-)-(26057-70-5)

Safety Data

• Hazardous Substances Data: 26057-70-5(Hazardous Substances Data)

Usage

Description

Avenaciolide is a water-insoluble fungal metabolite originally isolated from A. avenaceus. It inhibits glutamate transport in isolated rat liver mitochondria (Ki = 8 μM).

InChI:InChI=1/C15H22O4/c1-3-4-5-6-7-8-9-11-12-10(2)14(16)19-13(12)15(17)18-11/h11-13H,2-9H2,1H3

Upstream product

• 107977-48-0 (3α,3aα,4β,6aα)-(+/-)-Dihydro-4-octyl-3-<(phenylthio)methyl>furo<3,4-b>furan-2,6(3H,4H)-dione 
• 64-18-6 formic acid 
• 107977-44-6 (2α,3β(R^*))-(+/-)-Tetrahydro-4-methylene-α-<2-(trimethylsilyl)ethoxy>-2-octyl-5-oxo-3-furanacetic acid 
• 26191-78-6 (3aS,4S,6aS)-4-Octyl-2,6-dioxo-hexahydro-furo[3,4-b]furan-3-carboxylic acid 
• 107977-47-9 (2α,3β(R^*),4β)-(+/-)-Tetrahydro-α-hydroxy-2-octyl-5-oxo-4-<(phenylthio)methyl>-3-furanacetic acid methyl ester 
• 21369-64-2 n-hexyllithium 
• 124-19-6 nonan-1-al 
• 124929-01-7 2-((2R,3S,4S)-4-Iodo-2-octyl-5-oxo-tetrahydro-furan-3-yl)-2-phenylselanyl-propionic acid tert-butyl ester 
• 17756-68-2 5-octyl-5H-furan-2-one 

Relevant articles and documents

Efficient Synthesis of a Bislactone Skeleton Leading to dl-Avenaciolide

Treatment of 2-halodecanal and potassium ethyl malonate under phase-transfer catalysis condition gave ethyl tetrahydro-4-(ethoxycarbonyl)-2-octyl-5-oxo-3-furanacetate in one step.This compound was successfully converted into dihydro-4-octylfurofuran-2,6(3H,4H)-dione, which is an important key intermediate for the synthesis of dl-avenaciolide.

Total Synthesis of Natural Bicyclic Lactones (+)-Dihydrocanadensolide, (±)-Avenociolide, and (±)-Isoavenociolide via Tungsten-π-Allyl Complexes

A synthetic method using tungsten-π-allyl compounds is developed for total syntheses of natural bislactones including (+)-dihydrocanadensaolide (2), (±)-avenociolide (3), and (±)-isoavenociolide (4). Syntheses of these natural compounds are based on a com

Highly Enantioselective Synthesis of Both Enantiomers of γ-Substituted Butenolides by Bakers' Yeast Reduction and Lipase-Catalyzed Hydrolysis. Total Synthesis of (3AS,6aS)-Ethisolide, Whisky Lactone, and (-)-Avenaciolide

Reduction of 3-chloro-4-oxoalkanoates 5 with bakers' yeast gave (4S)-3-chloro-4-hydroxyalkanoates, which were hydrolyzed and dehydrochlorinated to give (γS)-alkylbutenolides with >96% ee. Reduction of 5 with NaBH4 gave syn-3-chloro-4-hydroxyalkanoate 6. Asymmetric hydrolysis of syn-4-chloro-3-hydroxyalkanoate (±)-10 with lipase afforded (3R,4R)-6 and (3S,4S)-10 with high optical purities. Hydrolysis and dehydrochlorination of (3R,4R)-6 gave (γA)-alkylbutenolides with >85% ee. Total syntheses of (3aS,6aS)-ethisolide, whisky lactone, and (-)-avenaciolide from these butenolides are described.