1,6-Dioxaspiro(4.4)nonane-2,7-dione

1,6-Dioxaspiro(4.4)nonane-2,7-dione
Names
Preferred IUPAC name
1,6-Dioxaspiro[4.4]nonane-2,7-dione
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.020.455
EC Number
  • 222-499-6
  • InChI=1S/C7H8O4/c8-5-1-3-7(10-5)4-2-6(9)11-7/h1-4H2
    Key: VTQYOGUFKHVWOO-UHFFFAOYSA-N
  • C1CC2(CCC(=O)O2)OC1=O
Properties
C7H8O4
Molar mass 156.14 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,6-Dioxaspiro[4.4]nonane-2,7-dione or spirodilactone is a spiro compound derived from the dicarboxylic acid 4,4-dihydroxypimelic acid, formed through double internal esterification into a symmetrical lactone. The short name spirodilactone is also occasionally used for the anellation Spiro[2-benzofuran-3,5'-oxolane]-1,2'-dione. The exceptionally straightforward synthesis of 1,6-dioxaspiro[4.4]nonane-2,7-dione from the platform chemical succinic acid offers promising prospects for future applications of this compound. The dilactone already serves as a starting material for heterocyclic pyrrolizidine, for the polyol 3-hydroxymethyl-1,3,6-hexanetriol, for esters of γ-ketopimelic acid, and as a dicarboxylic acid derivative for functional polymers such as polyethers and polyamides.

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