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212830

Sigma-Aldrich

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

95%

Sinonimo/i:

Danishefsky’s diene

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About This Item

Formula condensata:
(CH3)3SiOC(=CH2)CH=CHOCH3
Numero CAS:
54125-02-9
Peso molecolare:
172.30
Beilstein:
1616761
Numero MDL:
MFCD00008498
Codice UNSPSC:
12352100
ID PubChem:
24852745
NACRES:
NA.22

Livello qualitativo

100

Saggio

95%

Forma fisica

liquid

Impurezze

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

Indice di rifrazione

n20/D 1.454 (lit.)

P. eboll.

68-69 °C/14 mmHg (lit.)

Densità

0.885 g/mL at 25 °C (lit.)

Gruppo funzionale

ether

Temperatura di conservazione

2-8°C

Stringa SMILE

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+
SHALBPKEGDBVKK-VOTSOKGWSA-N

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Descrizione generale

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.

Applicazioni

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

Accessorio

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

Flame
GHS02

Avvertenze

Warning

Indicazioni di pericolo

H226

Classi di pericolo

Flam. Liq. 3

Codice della classe di stoccaggio

3 - Flammable liquids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

138.2 °F - closed cup

Punto d’infiammabilità (°C)

59 °C - closed cup

Dispositivi di protezione individuale

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

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Certificati d'analisi (COA)

Lot/Batch Number
SHBK6850
SHBF8895V
SHBF2984V
SHBD4654V
SHBD0072V

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Screening of rare earth metal grafted MCM-41 silica for asymmetric catalysis.
Gerstberger G and Anwander R.
Microporous and Mesoporous Materials : The Official Journal of the International Zeolite Association, 44, 303-310 (2001)
The Journal of Organic Chemistry, 57, 4444-4444 (1992)
Tetrahedron, 49, 397-397 (1993)
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
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
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