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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

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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)
Mingji Dai et al.
Journal of the American Chemical Society, 129(3), 645-657 (2007-01-18)
The paper describes the course of cycloadditions of Diels-Alder dienophiles containing linked enyne sites, each substituted with activating groups. Consistently, it was found that in the enyne cases the Diels-Alder reaction occurred specifically at the acetylenic center. Furthermore, it was
The Journal of Organic Chemistry, 57, 3605-3605 (1992)
Marie-Laure Teyssot et al.
The Journal of organic chemistry, 72(7), 2364-2373 (2007-03-10)
Electron-poor 6-oxo-1-sulfonyl-1,6-dihydropyridine-3-carboxylates 1b-d undergo cross-Diels-Alder reactions with electron-rich dienes 4a-f under hyperbaric conditions, reacting either as dienophiles to yield normal-electron-demand (NED) cycloadducts 10 and/or 11 or as dienes to give inverse-electron-demand (IED) cycloadducts 12 and/or 13. The latter are converted
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