| Identification | More | [Name]
(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde | [CAS]
78008-36-3 | [Synonyms]
(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CARBOXALDEHYDE
(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CARBOXYALDEHYDE
(R)-1,4-DIOXASPIRO[4.5]DECANE-2-CARBOXALDEHYDE
(R)-(+)-1,4-Dioxospiro(4,5)decane-2-carboxaldehyde
(+)-1,4-DIOXOSPIRO[4,5]DECANE-2-CABOXYALDEHYDE
1,4-DIOXASPIRO[4.5]DECANE-2-CARBOXALDEHYDE
(R)-(+)-2,2,CYCLOHEXYL-1,3-DIOXALANE-4-CARBOXALDEHYDE | [Molecular Formula]
C9H14O3 | [MDL Number]
MFCD07367804 | [Molecular Weight]
170.21 | [MOL File]
78008-36-3.mol |
| Chemical Properties | Back Directory | [Boiling point ]
271.2±25.0 °C(Predicted) | [density ]
1.108 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.472(lit.)
| [Fp ]
218 °F
| [storage temp. ]
Inert atmosphere,Store in freezer, under -20°C | [form ]
clear liquid | [color ]
Colorless to Light yellow | [Optical Rotation]
[α]/D 60±10° in chloroform | [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 | [SMILES]
O1C2(CCCCC2)OC[C@@H]1C=O | [CAS DataBase Reference]
78008-36-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
2932990090 | [Storage Class]
10 - Combustible liquids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
Reactant for:
- Proline-catalyzed Diels Alder reaction
- Stereodivergent synthesis of carbahexofuranoses employing a Wittig olefination-Claisen rearrangement protocol
- Wittig reactions
- Crotylation reactions
- Asymmetric synthesis of Goniothalesdiol A via stereocontrolled allylation and base-catalyzed oxy-Michael addition
| [Synthesis]
General procedure for the synthesis of (R)-1,4-dioxaspiro[4,5]decane-2-carbaldehyde from 1,2:5,6-di-O-cyclohexylidene-D-mannitol: a solution of sodium meta-periodide (NaIO4, 7.3 g, 34 mmol) and tetrabutylammonium bromide (phase transfer catalyst, 0.2 g, 0.62 mmol) in water (60 mL) was slowly added to a solution of 1,2. 5,6-di-O-cyclohexylidene-D-mannitol (10.0 g, 29.3 mmol) to a solution of tetrahydrofuran (THF, 100 mL). The reaction mixture was stirred at room temperature for 3 hours. After completion of the reaction, the organic layer was separated and the aqueous layer was extracted with ether (3 x 35 mL). The combined ether extracts were washed with water (1 x 35 mL) and dried with anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure to give a colorless viscous liquid (R)-1,4-dioxaspiro[4,5]decane-2-carboxaldehyde (compound (R)-8) in 90% yield (8.94 g). | [References]
[1] Synlett, 2011, # 8, p. 1154 - 1156
[2] Helvetica Chimica Acta, 2015, vol. 98, # 6, p. 823 - 833
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 36, p. 6195 - 6207
[4] Tetrahedron Letters, 2013, vol. 54, # 48, p. 6420 - 6422
[5] Organic Letters, 2017, vol. 19, # 16, p. 4167 - 4170 |
|
|