(2R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde

• ChemBase ID: 151123
• Molecular Formular: C9H14O3
• Molecular Mass: 170.20566
• Monoisotopic Mass: 170.09429431
• SMILES: C1CCC2(CC1)OC[C@@H](O2)C=O
• Canonical SMILES: O=C[C@H]1COC2(O1)CCCCC2
• InChI: InChI=1S/C9H14O3/c10-6-8-7-11-9(12-8)4-2-1-3-5-9/h6,8H,1-5,7H2/t8-/m0/s1
• InChIKey: FFGZPNNLXMQFMO-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde
• IUPAC Traditional name: (2R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde
• Synonyms: (R)-2,3-Cyclohexylideneglyceraldehyde; (R)-Cyclohexylideneglyceraldehyde; 2,3-O-Cyclohexylidene-D-glyceraldehyde; O,O-Cyclohexylidene-(R)-glyceraldehyde; (R)-1,4-Dioxaspiro[4.5]decane-2-carboxaldehyde; (R)-1,4-二氧杂螺[4.5]癸烷-2-甲醛

Database IDs

• CAS Number: 78008-36-3
• MDL Number: MFCD03093997
• PubChem SID: 24878656; 162245281
• PubChem CID: 10855919

CALCULATED PROPERTIES

• Acid pKa: 13.984845
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 1.2796578
• LogD (pH = 7.4): 1.2796578
• Log P: 1.2796578
• Molar Refractivity: 43.4015 cm^3
• Polarizability: 17.342642 Å^3
• Polar Surface Area: 35.53 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Density: 1.108 g/mL at 25 °C(lit.)
• Refractive Index: n20/D 1.472(lit.)
• Optical Rotation: [α]/D 60±10° in chloroform

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter

Product Information

• Empirical Formula (Hill Notation): C9H14O3

DETAILS

Sigma Aldrich - 543039

Application
Used as a building block.6
Reactant for:
• Proline-catalyzed Diels Alder reaction1
• Stereodivergent synthesis of carbahexofuranoses employing a Wittig olefination-Claisen rearrangement protocol2
• Wittig reactions3
• Crotylation reactions4
• Asymmetric synthesis of Goniothalesdiol A via stereocontrolled allylation and base-catalyzed oxy-Michael addition5
Other Notes
Contains varying amounts of polymer
Packaging
1 g in glass bottle