(3E,3aR,8bS)-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one

Base Information

• Chemical Name: (3E,3aR,8bS)-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one
• CAS No.: 76974-79-3
• Molecular Formula: C₁₇H₁₄O₅
• Molecular Weight: 298.295
• Hs Code.: 2932990090
• Nikkaji Number: J791.442C
• ChEMBL ID: CHEMBL4286026
• Mol file: 76974-79-3.mol

Synonyms:GR24;GR 24;(3E,3aR,8bS)-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one;76974-79-3;2H-Indeno(1,2-b)furan-2-one, 3-((((2R)-2,5-dihydro-4-methyl-5-oxo-2-furanyl)oxy)methylene)-3,3a,4,8b-tetrahydro-, (3E,3aR,8bS)-rel-;(+)-epi-GR-24;CHEMBL4286026;SCHEMBL13974737

Chemical Property of (3E,3aR,8bS)-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one

Chemical Property:

• Vapor Pressure: 6.66E-13mmHg at 25°C
• Boiling Point: 567.7°C at 760 mmHg
• Flash Point: 255°C
• PSA: 61.83000
• Density: 1.39g/cm³
• LogP: 2.18650
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 298.08412354
• Heavy Atom Count: 22
• Complexity: 576

Purity/Quality:

98%min ^*data from raw suppliers

StrigolactoneGR24 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(OC1=O)OC=C2C3CC4=CC=CC=C4C3OC2=O
• Isomeric SMILES: CC1=C[C@H](OC1=O)O/C=C/2\[C@H]3CC4=CC=CC=C4[C@H]3OC2=O
• Uses: Strigolactone GR24 is a terpenoid lactone that stimulates communication with arbuscular mycorrhizal fungi. It is also a plant hormone that stimulates and regulates shoot branching.

Technology Process of (3E,3aR,8bS)-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one

There total 2 articles about (3E,3aR,8bS)-3-[[(2S)-4-methyl-5-oxo-2H-furan-2-yl]oxymethylidene]-4,8b-dihydro-3aH-indeno[1,2-b]furan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-bromo-4-methyl-2H-furan-5-one (59488-94-7) + C12H10O3 → rac-(3aR,8bS,E)-3-(((S)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxymethylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one + contalactone + rac. (3aR,8bS,5'R)-3-<<(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo>methylene>-3,3a,4,8b-tetrahydroindeno<1,2-b>furan-2-one (76974-79-3,78647-00-4,80286-95-9)

Guidance literature:

With potassium carbonate; In acetone; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1016/j.phytochem.2019.112112

Reference yield:

2-bromo-4-methyl-2H-furan-5-one (59488-94-7) + Methyl formate (107-31-3) + cis-3,3a,4,8b-tetrahydro-2H-indeno<1,2-b>furan-2-one (4471-33-4,70667-72-0,78646-74-9) → rac-(3aR,8bS,E)-3-(((S)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl)oxymethylene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one + rac. (3aR,8bS,5'R)-3-<<(2,5-dihydro-3-methyl-2-oxo-5-furanyl)oxo>methylene>-3,3a,4,8b-tetrahydroindeno<1,2-b>furan-2-one (76974-79-3,78647-00-4,80286-95-9)

Guidance literature:

Methyl formate; cis-3,3a,4,8b-tetrahydro-2H-indeno<1,2-b>furan-2-one; With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

2-bromo-4-methyl-2H-furan-5-one; In 1,2-dimethoxyethane; Inert atmosphere;

DOI:10.1016/j.tet.2010.06.072

upstream raw materials:

2-bromo-4-methyl-2H-furan-5-one

Methyl formate

cis-3,3a,4,8b-tetrahydro-2H-indeno<1,2-b>furan-2-one

Refernces

• 1、 Malik, Heetika,Rutjes, Floris P.J.T.,Zwanenburg, Binne. "A new efficient synthesis of GR24 and dimethyl A-ring analogues, germinating agents for seeds of the parasitic weeds Striga and Orobanche spp.". experimental part. p. 7198 - 7203. Retrieved 2010/10/02.