6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione

• ChemBase ID: 140270
• Molecular Formular: C8H10O4
• Molecular Mass: 170.1626
• Monoisotopic Mass: 170.0579088
• SMILES: CC1(OC(=O)C2(CC2)C(=O)O1)C
• Canonical SMILES: O=C1OC(C)(C)OC(=O)C21CC2
• InChI: InChI=1S/C8H10O4/c1-7(2)11-5(9)8(3-4-8)6(10)12-7/h3-4H2,1-2H3
• InChIKey: AXJVPXNVESYGDT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione
• IUPAC Traditional name: 6,6-dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione
• Synonyms: 1,1-Cyclopropanedicarboxylic acid cyclic isopropylidene ester; 6,6-Dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione; cyclic Isopropylidene 1,1-cyclopropanedicarboxylate; 1,1-Cyclopropanedicarboxylic acid cycl-isopropylidene ester; cycl-Isopropylidene 1,1-cyclopropanedicarboxylate; 6,6-Dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione; 1,1-环丙烷二羧酸环异亚丙酯; 6,6-二甲基-5,7-二氧杂螺[2.5]辛烷-4,8-二酮; 1,1-环丙烷二甲酸环异亚丙酯; 6,6-二甲基-5,7-二氧杂螺[2.5]辛烷-4,8-二酮

Database IDs

• CAS Number: 5617-70-9
• EC Number: 227-044-5
• MDL Number: MFCD00042796
• Beilstein Number: 1241835
• PubChem SID: 162234514; 24858026; 24860919
• PubChem CID: 79720

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.0121171
• LogD (pH = 7.4): 1.0121171
• Log P: 1.0121171
• Molar Refractivity: 38.5039 cm^3
• Polarizability: 15.661688 Å^3
• Polar Surface Area: 52.6 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~65 °C; 63-65 °C(lit.); 63-66°C

Safety Information

• German water hazard class: 3
• TSCA Listed: 否
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (GC); 99%
• Grade: puriss.
• Impurities: ≤1% water
• Empirical Formula (Hill Notation): C8H10O4

DETAILS

Sigma Aldrich - 341266

Packaging
5 g in glass bottle

Sigma Aldrich - 29923

Other Notes
Highly activated cyclopropane for homoconjugate reactions1; For the generation of carbonylcyclopropane2; Review of electrophilic cyclopropanes3

REFERENCES

• Intermediate, introduced by Danishefsky, which undergoes homoconjugate additiion of nucleophiles, behaving as the synthetic equivalent of +CH₂CH₂CH(COOH)₂: J. Am. Chem. Soc., 97, 3239 (1975); J. Org. Chem., 40, 2969 (1975); 41, 1668 (1976). For an example in heterocyclic synthesis, see: Org. Synth. Coll., 7, 411 (1990):