1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one CAS 196597-78-1
1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Basic information
| Product Name: | 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one |
| Synonyms: | 1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one;1,2,6,7-Tetrahydro-8H-indeno[5,4-β]furan-8-one;RaMelteon I;4-b]furan-8-one;7-tetrahydro-;8H-Indeno[5;1,2,6,7-tetrahydroindeno[5,4-b]furan-8-one;Ramelteon Intermediate 1 |
| CAS: | 196597-78-1 |
| MF: | C11H10O2 |
| MW: | 174.2 |
| EINECS: | 1308068-626-2 |
| Product Categories: | Heterocycles;Aromatics Compounds;Aromatics |
| Mol File: | 196597-78-1.mol |
1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Chemical Properties
| Melting point | 149-1510C |
| Boiling point | 334.2±42.0 °C(Predicted) |
| density | 1.288±0.06 g/cm3(Predicted) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Chloroform (Slightly), Ethyl Acetate (Slightly) |
| form | Solid |
| color | White to Off-White |
| InChI | InChI=1S/C11H10O2/c12-9-3-1-7-2-4-10-8(11(7)9)5-6-13-10/h2,4H,1,3,5-6H2 |
| InChIKey | ZZUIZMWFNOKNLN-UHFFFAOYSA-N |
| SMILES | O1CCC2=C3C(CCC3=O)=CC=C12 |
| CAS DataBase Reference | 196597-78-1(CAS DataBase Reference) |
Safety Information
| HS Code | 2932.99.7000 |
| HazardClass | IRRITANT |
| Chemical Properties | White Solid |
| Uses | A tricyclic indan derivative as receptor agonist; a therapeutic agent for sleep disorders. |
| Synthesis | 196597-77-0 196597-78-1 4,5-Dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (280 kg, 843 mol) was used as a raw material, mixed with anhydrous sodium acetate (173 kg, 2109 mol) and methanol (6384 L). After the reaction system was replaced with nitrogen, 10% Pd/C catalyst (30.8 kg, dry weight) was added. Subsequently, the reaction mixture was pressurized to 0.29 to 0.49 MPa under a hydrogen atmosphere and catalytically reduced for 8 hours at about 40°C with a stirring rate such that the total gas-liquid mass transfer coefficient, KLa (1/hr), was about 15. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Water was added to the concentrated residue, concentrated again under reduced pressure to displace the solvent, cooled and stirred for 1 hour to mature the crystals. The crystallized solution was filtered to give wet 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one crystals (dry weight 127 kg, yield 86.6%). The amount of dimer in the wet crystals was less than 0.1 wt%. |
| References | [1] Journal of Medicinal Chemistry, 2002, vol. 45, # 19, p. 4222 - 4239 [2] Patent: EP1199304, 2002, A1. Location in patent: Referential example 18 [3] Patent: EP1792899, 2007, A1. Location in patent: Page/Page column 13 [4] Patent: CN103570651, 2016, B. Location in patent: Paragraph 0063; 0064 [5] Patent: US6348485, 2002, B1 |
1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Preparation Products And Raw materials
| Raw materials | 8H-Indeno[5,4-b]furan-8-one, 6,7-dihydro--->1-(2,3-dihydrobenzofuran-4-yl)ethanone-->Ethyl 3-(2,3-Dihydrobenzofuran-5-yl)propenoate-->2,3-Dihydrobenzo[b]furan-5-carbaldehyde-->3-(2,3-DIHYDRO-BENZOFURAN-5-YL)-PROPIONIC ACID ETHYL ESTER-->3-(6,7-Dibromo-2,3-dihydrobenzofuran-5-yl)propanoic Acid-->4,5-Dibromo-1,2,6,7-tertahydro-8H-indeno[5,4-b]furan-8-one-->(2E)-3-(2,3-DIHYDROBENZOFURAN-5-YL)PROPENOIC ACID-->Ethyl 3-(6,7-Dibromo-2,3-dihydro-1-benzofuran-5-yl)propanoate-->Ethyl 3-(7-Bromo-2,3-dihydro-1-benzofuran-5-yl)propanoate-->6-Hydroxy-1-indanone-->Formaldehyde-->2,3-Dihydrobenzofuran |
| Preparation Products | Ramelteon-->2H-Indeno[5,4-b]furan, 1,6,7,8-tetrahydro--->2,6,7,8-Tetrahydro-1H-indeno[5,4-b]furan-8-ylethylamine |
