423424
2-(Trimethylsiloxy)-1,3-cyclohexadiene
95%
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About This Item
Empirical Formula (Hill Notation):
C9H16OSi
CAS Number:
Molecular Weight:
168.31
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
2079140
Assay:
95%
Form:
liquid
Product Name
2-(Trimethylsiloxy)-1,3-cyclohexadiene, 95%
InChI
1S/C9H16OSi/c1-11(2,3)10-9-7-5-4-6-8-9/h5,7-8H,4,6H2,1-3H3
SMILES string
C[Si](C)(C)OC1=CCCC=C1
InChI key
WPIRVUXAMPRMAY-UHFFFAOYSA-N
assay
95%
form
liquid
refractive index
n20/D 1.462 (lit.)
bp
65 °C/7 mmHg (lit.)
density
0.899 g/mL at 25 °C (lit.)
storage temp.
2-8°C
Quality Level
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Application
2-(Trimethylsiloxy)-1,3-cyclohexadiene may be used as a diene in the synthesis of isoquinuclidinone 2-aza[2.2.2]octa-3,5-dione by reacting with p-toluenesulfonyl cyanide.
General description
2-(Trimethylsiloxy)-1,3-cyclohexadiene ((cyclohexa-1,5-dien-1-yloxy)trimethylsilane) is silyl enol ether of cyclohexenone. The Diels–Alder reactions with dienophiles α-acetoxyacrylonitrile, acrylonitrile and α-chloroacrylonitrile has been studied.
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High-Temperature Diels-Alder Reactions: Transfer from Batch to Continuous Mode.
Abele S, et al.
Organic Process Research & Development, 16(5), 1114-1120 (2011)
Safety Assessment of Diels-Alder Reactions with Highly Reactive Acrylic Monomers.
Abele S, et al.
Organic Process Research & Development, 16(12), 2015-2020 (2012)
Cynthia K McClure et al.
The Journal of organic chemistry, 68(21), 8256-8257 (2003-10-11)
The hetero-Diels-Alder reaction of an electron-deficient nitrile, p-toluenesulfonyl cyanide, with the silyl enol ether of cyclohexenone produced a hydrolytically sensitive [4 + 2] adduct in good yield. Use of Mander's reagent, ethyl cyanoformate, with the same diene, produced an unstable
Design and Scale-Up of Diels-Alder Reactions for the Practical Synthesis of 5-Phenylbicyclo [2.2. 2] oct-5-en-2-one.
Funel JA, et al.
Organic Process Research & Development, 15(6), 1420-1427 (2011)
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