1073-11-6

Basic information

• Product Name: dihydro-5-methyl-5-vinylfuran-2(3H)-one
• Synonyms: dihydro-5-methyl-5-vinylfuran-2(3H)-one;4-HYDROXY-4-METHYL-5-HEXENOICACIDGAMMALACTONE;4,5-Dihydro-5-ethenyl-5-methylfuran-2(3H)-one;4,5-Dihydro-5-methyl-5-vinyl-2(3H)-furanone;5-Methyl-5-ethenyl-4,5-dihydrofuran-2(3H)-one;Lavender lactone;γ-Vinyl-γ-Valerolactone;5-Ethenyldihydro-5-methyl-2(3H)-furanone
• CAS NO: 1073-11-6
• Molecular Formula: C₇H₁₀O₂
• Molecular Weight: 126.1531
• EINECS: 214-024-6
• Mol File: 1073-11-6.mol
• Article Data: 15

Chemical Properties

• Boiling Point: 205.9°Cat760mmHg
• Flash Point: 74.6°C
• Appearance: /
• Density: 1.091g/cm³
• Vapor Pressure: 0.244mmHg at 25°C
• Refractive Index: 1.527
• CAS DataBase Reference: dihydro-5-methyl-5-vinylfuran-2(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: dihydro-5-methyl-5-vinylfuran-2(3H)-one(1073-11-6)
• EPA Substance Registry System: dihydro-5-methyl-5-vinylfuran-2(3H)-one(1073-11-6)

Safety Data

• Hazardous Substances Data: 1073-11-6(Hazardous Substances Data)

Usage

Chemical Properties

4-Hydroxy-4-methyl-5-hexenoic acid gamma-lactone has a floral aroma.

Occurrence

Reportedly present in papaya, wine, tea, grapes (Vitis vinifera), coriander seed, calamus, sage and maté

Uses

4-Methyl-4-vinyl-4-butanolide is an intermediate in the synthesis of γ-CEHC (C249200) which is a metabolite of γ-Tocopherol (T526140); one of the naturally occurring forms of Vitamin E found most abundantly in soybean and corn oils.

InChI:InChI=1/C7H10O2/c1-3-7(2)5-4-6(8)9-7/h3H,1,4-5H2,2H3

Upstream product

• 60047-17-8 2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran 
• 1826-67-1 vinyl magnesium bromide 
• 3536-96-7 vinylmagnesium chloride 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 71328-53-5 5-(1'-bromo-1'-methyl) ethyl-2-methyl-2-vinyltetrahydrofurane 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 67304-14-7 2-methyl-2-vinyl-5-isopropylidenetetrahydrofuran 

Downstream Products

• 178167-77-6 racemic 2,7,8-trimethyl-2-(β-carboxyethyl) chroman 
• 1091618-53-9 C₁₇H₁₉NO₄ 
• 1091618-50-6 C₁₇H₁₉NO₄ 
• 3121-68-4 2,3,5-trimethyl-6-(2-(2-methyl-5-oxotetrahydrofuran-2-yl)ethyl)cvclohexa-2,5-diene-1,4-dione 
• 18794-84-8 (E)-β-farnesene 
• 4072-32-6 racemic 2,5,7,8-tetramethyl-2-(β-carboxyethyl)-6-hydroxy chroman 

Relevant articles and documents

Stereoselective synthesis of 1-methyl-1,2-and 1,3-cyclopentanediols via γ-lactones

A method for the synthesis of 1-methylcarbapentofuranose derivatives was developed, where 1,2-cis- and 1,2-trans-4-hydroxymethyl-1- methylcyclopentanediols were obtained from intramolecular opening of a 4-epoxy-4-methyl-γ-lactone. An intramolecular aldol reaction of 4-methyl-4-(2-oxoethyl)-γ-lactone derivatives yielded 1,3-cis- and 1,3-trans-4-hydroxymethyl-1-methylcyclopentanediols.

Palladium-Catalyzed Cyclization of Free Hydroxyalkenoic Acids: Regio- and Chemoselective Access to Methylene Lactones

A general and collective synthesis of medium-sized methylene lactones via controlled cyclizations of easily accessible collective precursors is described. The rapid composition of key–hydroxyalkenoic acid scaffold yields an assembly of oxocanones, oxepanones, and pyranones in a regioselective and stereodirected fashion via palladium-catalyzed cyclization. (Figure presented.).

CYCLIZATION PROCESSES OF HYDROXYALKENOIC AICDS AND PRODUCTS THEREOF

The invention provides efficient cyclization processes of hydroxyalkenoic acids and products produced therefrom. The following reactions are claimed: Formula (I), (II), (V) and (VI).