1-Methoxy-3-trimethylsiloxy-1,3-butadiene, 96%

Name: 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, 96%
SKU: L14672.03
Price: 59.20 EUR

CAS: 54125-02-9 | C8H16O2Si | 172.299 g/mol

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Catalog number L14672.03

also known as L14672-03

Price (EUR)

59,20

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Quantity:

1 g

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Price (EUR)

59,20

Each

Chemical Identifiers

CAS54125-02-9

IUPAC Name[(4-methoxybuta-1,3-dien-2-yl)oxy]trimethylsilane

Molecular FormulaC8H16O2Si

InChI KeySHALBPKEGDBVKK-UHFFFAOYSA-N

SMILESCOC=CC(=C)O[Si](C)(C)C

Specifications

Specification Sheet

FormLiquid

Refractive Index1.4525-1.4575 @ 20°C

Assay (GC)≥94.0%

Appearance (Color)Clear colorless to yellow

1-Methoxy-3-trimethylsiloxy-1,3-butadiene is employed as a reagent in Mannich-Michael reaction for the synthesis of piperidinones and enaminones. As Diels-Alder diene, it is used in the synthesis of pyridones and pyranones, sulfone analogues of griseofulvin (sulfogriseofulvins) and 4H-1-aminopyrroles and 4, 5H-pyrazoles.

This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications
1-Methoxy-3-trimethylsiloxy-1,3-butadiene is employed as a reagent in Mannich-Michael reaction for the synthesis of piperidinones and enaminones. As Diels-Alder diene, it is used in the synthesis of pyridones and pyranones, sulfone analogues of griseofulvin (sulfogriseofulvins) and 4H-1-aminopyrroles and 4, 5H-pyrazoles.

Solubility
Miscible with most organic solvents. Immiscible with water.

Notes
Moisture sensitive. Store in cool place. Incompatible with strong oxidizing agents and strong acids.

RUO – Research Use Only

General References:

High purity grade.
Oxygen-functionalized diene, useful for the regiospecific introduction of cyclohexanone or cyclohexenone groupings by cycloaddition with dienophiles: J. Am. Chem. Soc., 96, 7807 (1974); 100, 6536, 7098 (1978). Review: Acc. Chem. Res., 14, 400 (1981); review of cycloaddition reactions of silyloxydienes: Synthesis, 85 (1983); example and discussion: Org. Synth. Coll., 7, 312 (1990):
An improved procedure for the conversion of the initial adducts to enones involves treatment with TMS-OTf: J. Org. Chem., 55, 3693 (1990).
For cycloaddition to phenyl vinyl sulfone, see: J. Org. Chem., 48, 4986 (1983). Details have been given for the addition to a cyclic vinyl sulfone: Org. Synth. Coll., 8, 38 (1993).
The diene also undergoes cycloaddition reactions with heterodienophiles. Thus addition to carbonyl groups gives 2,3-dihydro--pyrones: J. Am. Chem. Soc., 104, 358 (1982); Heterocycles, 32, 273 (1991). See also Tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato) europium(III), 33541. For asymmetric Diels-Alder reaction with aldehydes, mediated by a chiral Lewis acid derived from BINOL ((R)-(+)-1,1'-Bi(2-naphthol) , L08305) and Ti(O-i-Pr)₄, see: J. Org. Chem., 60, 5998 (1995):
Reaction with imines in the presence of ZnCl₂ leads to 4-oxotetrahydropyridines: Tetrahedron Lett., 23, 3739 (1982). For an example in synthesis of the manzamine marine alkaloids, see: J. Org. Chem., 57, 5741 (1992); J. Am. Chem. Soc., 117, 2363 (1995). For enantioselective asymmetric Diels-Alder reaction with an imine catalyzed by a BINOL boron Lewis acid, see: Tetrahedron, 49, 1749 (1993). For aza Diels-Alder reactions with imines in water under neutral conditions, see: Chem. Commun., 574 (2003).
For cycloaddition to Fullerene powder, 39722, see: J. Org. Chem., 60, 6353 (1995).