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212830

Sigma-Aldrich

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene

95%

Synonym(s):

Danishefsky’s diene

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About This Item

Linear Formula:
(CH3)3SiOC(=CH2)CH=CHOCH3
CAS Number:
54125-02-9
Molecular Weight:
172.30
Beilstein:
1616761
MDL number:
MFCD00008498
UNSPSC Code:
12352100
PubChem Substance ID:
24852745
NACRES:
NA.22

Assay

95%

form

liquid

impurities

2-5% 4-methoxy-3-buten-2-one

refractive index

n20/D 1.454 (lit.)

bp

68-69 °C/14 mmHg (lit.)

density

0.885 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CO\C=C\C(=C)O[Si](C)(C)C

InChI

1S/C8H16O2Si/c1-8(6-7-9-2)10-11(3,4)5/h6-7H,1H2,2-5H3/b7-6+

InChI key

SHALBPKEGDBVKK-VOTSOKGWSA-N

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General description

trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene is a funtionalized Diels-Alder diene. Mukaiyama-Michael-type addition/heterocyclization of trans-1-methoxy-3-trimethylsiloxy-1,3-butadiene (Danishefsky′s diene) with 1,2-diaza-1,3-butadiene has been investigated. Asymmetric hetero-Diels-Alder cyclization of Danishefsky′s diene with benzaldehyde catalyzed by mesoporous inorganic/metalorganic hybrid materials has been reported.

Application

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene was used:
  • in the synthesis of sulfone analogues of griseofulvin (sulfogriseofulvins), 4H-1-aminopyrroles and 4,5H-pyrazoles
  • as Diels-Alder diene for the synthesis of pyridones and pyranones
  • as reagent employed in the Mannich-Michael reaction for preparation of piperidinones and enaminones

accessory

Product No.
Description
Pricing

Pictograms

Flame
GHS02

Signal Word

Warning

Hazard Statements

H226

Hazard Classifications

Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

138.2 °F - closed cup

Flash Point(C)

59 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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M Friedrich et al.
Archiv der Pharmazie, 329(7), 361-370 (1996-07-01)
Syntheses of substituted, especially of fluoro substituted benzoxathiole 1,1-dioxides, are described. These derivatives were transformed via the Peterson olefination into substituted 2-alkylidene derivatives 27. Diels-Alder reactions of 27 with 1,1-dimethoxy- and 1-methoxy-3-trimethylsiloxy-1,3-butadiene (30, 32) gave sulfone analogues 31 of griseofulvin
The Journal of Organic Chemistry, 57, 4444-4444 (1992)
Tetrahedron, 49, 397-397 (1993)
Orazio A Attanasi et al.
Organic letters, 10(10), 1983-1986 (2008-04-23)
The versatility of the Mukaiyama-Michael-type addition/heterocyclization of Danishefsky's diene with 1,2-diaza-1,3-butadienes was applied to the synthesis of both 4 H-1-aminopyrroles and 4,5 H-pyrazoles. Thus, the same reagents furnished different types of highly functionalized azaheterocycles essentially depending on their structure: as
Tetrahedron, 49, 1749-1749 (1993)
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