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About This Item
Empirical Formula (Hill Notation):
C10H22O2Si2
CAS Number:
Molecular Weight:
230.45
Beilstein:
1367530
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
Recommended Products
Assay
≥95%
refractive index
n20/D 1.435 (lit.)
bp
58-59 °C/2 mmHg (lit.)
density
0.897 g/mL at 25 °C (lit.)
SMILES string
C[Si](C)(C)OC1=C(CC1)O[Si](C)(C)C
InChI
1S/C10H22O2Si2/c1-13(2,3)11-9-7-8-10(9)12-14(4,5)6/h7-8H2,1-6H3
InChI key
WOBRFSDEZREQAB-UHFFFAOYSA-N
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General description
Photocycloaddition of 2-cyclohexenones to 1,2-bis(trimethyl-siloxy)cyclobutene has been studied. It undergoes Aldol condensation reaction with carbonyl compounds. It reacts with Br2 to give cyclobutanedione.
Application
1,2-Bis(trimethylsiloxy)cyclobutene has been used in the synthesis of:
- functionalized decalins, required for the total synthesis of various sesquiterpenes and diterpenes
- angularly substituted bicyclo[4.3.0]nona-2,5-diones and bicyclo-[4.4.0]deca-2,5-diones
- 3-methoxyestra-1,3,5,8,14-pentaen-17-one
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
141.8 °F - closed cup
Flash Point(C)
61 °C - closed cup
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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A very short synthesis of 3-methoxyestra-1, 3, 5, 8, 14-pentaen-17-one.
Burnell DJ and Wu Y-J.
Canadian Journal of Chemistry, 67(5), 816-819 (1985)
Journal of the American Chemical Society, 106, 1759-1759 (1984)
Organic Syntheses, 7, 112-112 (1990)
Photoaddition with 1, 2-bis (trimethylsiloxy) cyclobutene: a versatile entry to the stereocontrolled total synthesis of various sesquiterpenes and diterpenes.
de Keukeleire D, et al.
Journal of Photochemistry, 28(2), 165-174 (1985)
A (Π2+ Π2) photocycloaddition reaction as a facile route to angularly substituted cis-hydrindanes and cis-decalanes.
Van Audenhove M, et al.
Tetrahedron Letters, 21(20), 1979-1982 (1980)
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