CAS 762-72-1|silane, trimethyl-2-propenyl-|trimethyl(prop-2-en-1-yl)silane|ALLYL TRIMETHYLSILANE|烯丙基三甲基硅烷|3-(Trimethylsilyl)propene|3-(三甲基甲硅烷基)丙烯|Allyltrimethylsilane|Allyltrimethyl...

General Information

Structure

Molecular Formula

C₆H₁₄Si

Molecular Mass

114.26086

Exact Mass

114.08647698

Charge

InChI

InChI=1S/C6H14Si/c1-5-6-7(2,3)4/h5H,1,6H2,2-4H3

InChIKey

HYWCXWRMUZYRPH-UHFFFAOYSA-N

Canonic Smiles

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

Isomeric Smiles

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

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

2.9051

LogD (pH = 7.4)

2.9051

Log P

2.9051

Molar Refractivity

31.4083

Polarizability

14.499341

Polar Surface Area

0.0

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

silane, trimethyl-2-propenyl-

IUPAC name

trimethyl(prop-2-en-1-yl)silane

Synonyms

ALLYL TRIMETHYLSILANE烯丙基三甲基硅烷3-(Trimethylsilyl)propene3-(三甲基甲硅烷基)丙烯AllyltrimethylsilaneAllyltrimethylsilane

Names and Identifiers

Registration numbers

EC Number

CAS Number

Beilstein Number

PubChem SID

MDL Number

PubChem CID

Registration numbers

Properties

Related Proteins

Molecular Spectra

No Data Available

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Molecule Details

Sigma Aldrich

208264

Packaging
10, 50 g in glass bottle

MP Biomedicals

05203439

MP Biomedicals Rare Chemical collection

Molecule Details

References

PubChem Literature

From Data Sources

• More recent studies have shown that TMS cyclopentanes are also formed in these reactions via a competing [3+2] cycloaddition mechanism: Tetrahedron, 49, 9955 (1993). Chemoselective addition to aldehydes can be accomplished in the presence of a ketone, using Scandium(III) trifluoromethanesulfonate hydrate, 40566 as catalyst: Synthesis, 1822 (1998).

• Similarly, carbonyl compounds are converted to homoallylic alcohols: J. Organomet. Chem., 69, C15 (1974). In the TiCl₄ promoted reaction with enones, behaves as an allyl anion equivalent, giving the product of conjugate addition (Hosomi-Sakurai reaction): J. Am. Chem. Soc., 99, 1673 (1977);105, 2354 (1983); Org. Synth. Coll., 7, 443 (1990):

• In the presence of F^-, functions as an allyl anion equivalent, affording homoallylic alcohols from carbonyl compounds: Tetrahedron Lett., 3043 (1978), and adding to a variety of Michael acceptors: Tetrahedron Lett., 25, 3213 (1984); J. Org. Chem., 51, 1745 (1986). For a review of reactivity in the presence of Lewis acids and F^-, see: J. Prakt. Chem./ Chem. Ztg., 336, 375 (1994).

• Reactions with electrophiles illustrate the ?-effect (see Appendix 4); e.g. acid chlorides with a Lewis acid give allyl ketones: J. Organomet. Chem., 85, 149 (1975):

• Has also been used, in the presence of a catalyst such as p-TsOH, I₂, Br₂ or TfOH, as a silylating agent for alcohols, phenols and carboxylic acids: Tetrahedron Lett., 21, 835 (1980); J. Org. Chem., 46, 5212 (1981). The advantage over more conventional silylation methods is that the only by-product is the neutral gas propene.

References

Bioactivity

PubChem BioAssay

Bioactivity

References

PubChem Literature

From Data Sources

• Reactions with electrophiles illustrate the ?-effect (see Appendix 4); e.g. acid chlorides with a Lewis acid give allyl ketones: J. Organomet. Chem., 85, 149 (1975):

Bioactivity

PubChem BioAssay