(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde Chemical Properties

Boiling point:

271.2±25.0 °C(Predicted)

Density 

1.108 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.472(lit.)

Flash point:

218 °F

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

clear liquid

color 

Colorless to Light yellow

optical activity

[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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

2932990090

Storage Class

10 - Combustible liquids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:SigmaAldrich

(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde Usage And Synthesis

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

(R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde(78008-36-3)Related Product Information

• DIOXOPROMETHAZINE HCL
• Decane
• 1,4-Dioxane
• Selenium dioxide
• 1-Bromodecane
• (R)-(+)-2,2-Dimethyl-1,3-dioxolane-4-carboxaldehyde
• DIOXOPROMETHAZINE
• 2,3-O-(3-PENTYLIDENE)-D-GLYCERALDEHYDE
• RARECHEM AL BP 0891
• 2,3-CYCLOHEXYLIDENE-D-RIBONIC ACID GAMMA-LACTONE
• (R)-1,4-Dioxaspiro[4,5]decane-2-carboxaldehyde