668-10-0

Basic information

• Product Name: Ammiol
• Synonyms: Ammiol;7-(Hydroxymethyl)-4,9-dimethoxy-5H-furo[3,2-g][1]benzopyran-5-one
• CAS NO: 668-10-0
• Molecular Formula: C₁₄H₁₂O₆
• Molecular Weight: 276.24
• Mol File: 668-10-0.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 503.7°C at 760 mmHg
• Flash Point: 258.4°C
• Appearance: /
• Density: 1.391g/cm³
• Vapor Pressure: 5.77E-11mmHg at 25°C
• Refractive Index: 1.617
• CAS DataBase Reference: Ammiol(CAS DataBase Reference)
• NIST Chemistry Reference: Ammiol(668-10-0)
• EPA Substance Registry System: Ammiol(668-10-0)

Safety Data

• Hazardous Substances Data: 668-10-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H12O6/c1-17-11-8-3-4-19-12(8)14(18-2)13-10(11)9(16)5-7(6-15)20-13/h3-5,15H,6H2,1-2H3

Upstream product

• 88897-90-9 4,9-Dimethoxy-7<(methylthio)acetoxymethyl>-5H-furo<3,2-g><1>benzopyran-5-one 
• 76301-44-5 4,9-Dimethoxy-7-<(methylsulfinyl)methyl>-5H-furo<3,2-g><1>benzopyran-5-one 
• 76301-19-4 4,9-Dimethoxy-7--5H-furo<3,2-g><1>benzopyran-5-one 
• 82-02-0 Khellin 
• 484-51-5 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran 
• 93454-52-5 khellin-2-carboxaldehyde 
• 93454-53-6 4,9-Dimethoxy-7-(iodomethyl)-5H-furo<3,2-g><1>benzopyran-5-one 

Downstream Products

• 484-51-5 5-acetyl-6-hydroxy-4,7-dimethoxybenzofuran 

Relevant articles and documents

The Synthesis and Chemistry of Functionalized Furochromones. 2. The Synthesis, Sommelet-Hauser Rearrangement, and Conversion of 4,9-Dimethoxy-7--5H-furobenzopyran-5-one to Ammiol

Condensation (NaH/THF) of khellinone 14 with ethyl 2-(methylthio)acetate followed by acid-catalyzed cyclodehydration in methanolic HCl yielded 4,9-dimethoxy-7--5H-furobenzopyran-5-one (10).Condensation of 14 with ethyl 2-(phenylthio)acetate followed by cyclodehydration yielded the corresponding C-7 (phenylthio)methylene analogue 11.Sulfide 10 was converted to sulfonium salt 17 which upon treatment with base yielded the rearranged sulfide 18, 4,9-dimethoxy-6--7-methyl-5H-furobenzopyran-5-one.Desulfurization of 18 yielded the 6,7-dimethylfurochromone 19 while treatment of both 18 and 10 with N,N-dimethylformamide dimethyl acetal yielded 20 and 21, respectively.Periodate oxidation of 10 yielded sulfoxide 24 which underwent Pummerer rearrangement to give acetoxy sulfide 25.Hydrolysis of 25 (to give 2) and Meerwein-Ponndorf-Verley reduction then yielded ammiol 4.Treatment of 10 with excess methyl iodide yielded the known allylic iodide 5. treatment of 5 with KO2 or KOAc and then basic hydrolysis of that acetate likewise yielded ammiol.Treatment of 5 with N,N-dimethylamine afforded the C-7 aminomethylene analogue 27 in 96percent yield.