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

1,2,6,7-Tetrahydro-8H-indeno[5,4-b]furan-8-one Usage And Synthesis

Chemical Properties

White Solid

Uses

A tricyclic indan derivative as receptor agonist; a therapeutic agent for sleep disorders.

Synthesis

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

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