141262-39-7

Basic information

• Product Name: (3E,3aR,8S,8bS)-8-methyl-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylidene)-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[1,2-b]furan-2-one
• CAS NO: 141262-39-7
• Molecular Formula: C₁₈H₂₀O₅
• Molecular Weight: 316.3484
• Mol File: 141262-39-7.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 600.6°C at 760 mmHg
• Flash Point: 267.3°C
• Density: 1.29g/cm³
• Vapor Pressure: 2.2E-14mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: (3E,3aR,8S,8bS)-8-methyl-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylidene)-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[1,2-b]furan-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3E,3aR,8S,8bS)-8-methyl-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylidene)-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[1,2-b]furan-2-one(141262-39-7)
• EPA Substance Registry System: (3E,3aR,8S,8bS)-8-methyl-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylidene)-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[1,2-b]furan-2-one(141262-39-7)

Safety Data

• Hazardous Substances Data: 141262-39-7(Hazardous Substances Data)

Upstream product

• 59488-94-7 2-bromo-4-methyl-2H-furan-5-one 
• 251116-03-7 (3aS,8S,8bR)-3-hydroxymethylene-8-methyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one 
• 198642-01-2 (3aR,8S,8bS)-3-hydroxymethylene-8-methyl-3,3a,4,5,6,7,8,8b-octahydroindeno[1,2-b]furan-2-one 
• 66510-25-6 2-chloro-4-methyl-2H-furan-5-one 
• 202340-60-1 (3aR,8R,8bS)-8-Methyl-3-[1-((1S,2R,3R,6S,7R)-6-methyl-5-oxo-4-oxa-tricyclo[5.2.1.0^2,6]dec-8-en-3-yloxy)-meth-(E)-ylidene]-3,3a,4,5,6,7,8,8b-octahydro-indeno[1,2-b]furan-2-one 
• 109-94-4 formic acid ethyl ester 
• 5949-05-3 (S)-Citronellal 
• 2111-53-7 (S)-(-)-citronellic acid 
• 56994-89-9 (S)-(-)-citronellic acid,methyl ester 
• 120888-48-4 (S)-3-Methyl-6-oxo-hexanoic acid methyl ester 
• 183479-46-1 2,3,4,5,6,7-Hexahydro-2-carboxymethyl-7-methylindene-1,4-dione 
• 158661-84-8 methyl (S)-6-hydroxy-3-methylhexanoate 
• 198641-93-9 methyl (S)-3-methyl-7-octynoate 
• 198641-92-8 methyl (S)-6-iodo-3-methylhexanoate 

Relevant articles and documents

Synthesis and biological evaluation of the four racemic stereoisomers of the structure proposed for sorgolactone, the germination stimulant from Sorghum bicolor

The synthesis of the racemates of the structure 1 proposed for sorgolactone and its three stereoisomers was achieved by confirming the stereostructures of the intermediate (±)-6 and the final product (±)-1 by X-ray analyses. Biological evaluation of the products employing clover broomrape (Orobanche minor) seeds revealed that the order of activity as a germination stimulant was (±)-strigol ~ (±)-9 ≤ (±)-12 > (±)-1 > (±)-11.

The first total synthesis of the naturally occurring germination stimulant sorgolactone

The first total synthesis of sorgolactone is reported, which confirms the proposed structure of the naturally occurring germination stimulant.

Synthesis of (3aR,8S,8bS,2'R)-(+)-sorgolactone and its stereoisomers, the germination stimulant from sorghum bicolor

Methyl (S)-citronellate (2) was converted to (3aR,8S,8bS,2'R)-(+)- sorgolactone (1a) by employing the radical cyclization of 6 to 7 as the key- step. Three other stereoisomers (1b, 1c and 1d) of sorgolactone were also prepared. The CD spectrum of la was in accord with that reported for the natural product.