666246
1-(2-Methoxyethoxy)-1-vinylcyclopropane
Synonym(s):
1-Ethenyl-1-(2-methoxyethoxy)cyclopropane
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About This Item
Empirical Formula (Hill Notation):
C8H14O2
CAS Number:
Molecular Weight:
142.20
UNSPSC Code:
12352100
PubChem Substance ID:
MDL number:
refractive index
n20/D 1.441
density
0.922 g/mL at 25 °C
storage temp.
2-8°C
SMILES string
COCCOC1(CC1)C=C
InChI
1S/C8H14O2/c1-3-8(4-5-8)10-7-6-9-2/h3H,1,4-7H2,2H3
InChI key
YIUPAIQJWAOJKD-UHFFFAOYSA-N
Application
A useful scaffold for the preparation of 7-membered and bicyclic ring systems.
Capable of participating in a variety of rhodium-catalyzed cycloaddition reactions.
Reactant for:
- Rhodium-catalyzed [5+2] cycloaddition with alkynes and allenes
- Cycloaddition/Nazarov cyclization sequence reactions
- Preparation of cyclohexenones by cocyclization with carbon monoxide catalyzed by octacarbonyldicobalt
- Preparation of cyclopentenes by nickel-catalyzed isomerization
signalword
Warning
hcodes
pcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 3
Storage Class
3 - Flammable liquids
wgk
WGK 3
flash_point_f
114.8 °F
flash_point_c
46 °C
ppe
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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Hermann A Wegner et al.
Journal of the American Chemical Society, 127(18), 6530-6531 (2005-05-05)
Initial examples of the intermolecular Rh(I)-catalyzed [5+2] cycloaddition reaction of bifunctional allenes and vinylcyclopropanes are described. The reactions proceed with facility and in yields of up to 99% with a variety of alkyne-, ester-, styrene-, or cyano-substituents on the allene
Zhi-Xiang Yu et al.
Journal of the American Chemical Society, 126(30), 9154-9155 (2004-07-30)
DFT calculations have been applied to investigate the reaction mechanism of rhodium dimer, [Rh(CO)2Cl]2, catalyzed intermolecular (5 + 2) reactions between vinylcyclopropanes and alkynes. The catalytic species is Rh(CO)Cl and the catalytic cycle is through the sequential reactions of cyclopropyl
Paul A Wender et al.
Journal of the American Chemical Society, 124(12), 2876-2877 (2002-03-21)
Prompted by our studies of transition metal-catalyzed [4+4], [4+2], [5+2], and [6+2] cycloadditions and by the view that these two-component reactions could be intercepted by a third component of one or more atoms, a new three-component transition metal-catalyzed cycloaddition is