| Identification | Back Directory | [Name]
4,4-Dimethyl-3,5,8-trioxabic-yclo[5,1,0]Octane | [CAS]
57280-22-5 | [Synonyms]
0]Octane
4-Dimethyl-3
8-trioxabic-yclo[5
Gadobutrol Impurity 49
4,4-Dimethyl-3,5,8-trioxabic-yclo[5,1,0]Octane
3,5,8-Trioxabicyclo[5.1.0]octane, 4,4-diMethyl-
4,4-diMethyl-3,5,8-trioxabicyclo[5.1.0]octane(EP2)
4 4-DIMETHYL-3 5 8-TRIOXABICYCLO (5.1.0)OCTANE TOBO
4,4-Dimethyl-3,5,8-trioxabic-yclo[5.1.0]octane(DTC-octane) | [EINECS(EC#)]
421-750-9 | [Molecular Formula]
C7H12O3 | [MDL Number]
MFCD16621162 | [MOL File]
57280-22-5.mol | [Molecular Weight]
144.17 |
| Chemical Properties | Back Directory | [Boiling point ]
179℃ | [density ]
1.071 | [refractive index ]
1.4560 to 1.4600 | [Fp ]
56℃ | [storage temp. ]
Inert atmosphere,2-8°C | [form ]
clear liquid | [color ]
Colorless to Light yellow to Light orange | [InChI]
InChI=1S/C7H12O3/c1-7(2)8-3-5-6(10-5)4-9-7/h5-6H,3-4H2,1-2H3 | [InChIKey]
GEKNCWQQNMEIMS-UHFFFAOYSA-N | [SMILES]
C12C(O1)COC(C)(C)OC2 |
| Hazard Information | Back Directory | [Chemical Properties]
Clear colorless to yellow liquid | [Uses]
4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane is used in the CO2-mediated formation of chiral carbamates from meso-epoxides via polycarbonate intermediates and amine nucleophiles, which opens up a wide a wide range of CO2-based carbamate scaffolds with excellent yields and 99% enantiomeric excess. | [Application]
4, 4-dimethyl-3,5, 8-trioxane [5,1,0] octane is a key intermediate in the preparation of gadobinol. As a meso epoxide, it could be used to obtain optically pure ABT derivatives through Ti(IV)/BINOL catalyzed asymmetric aminolysis[1]. | [References]
[1] Bao H, et al. Insight into the Mechanism of the Asymmetric Ring-Opening Aminolysis of 4,4-Dimethyl-3,5,8-trioxabicyclo[5.1.0]octane Catalyzed by Titanium/BINOLate/Water System: Evidence for the Ti(BINOLate)2-Bearing Active Catalyst Entities and the Role of Water. Journal of the American Chemical Society, 2008; 130: 10116–10127.
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