212830

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

95%

• Sinônimo(s): Danishefsky’s diene
• Fórmula linear: (CH₃)₃SiOC(=CH₂)CH=CHOCH₃
• Número CAS: 54125-02-9
• Peso molecular: 172.30
• Beilstein: 1616761
• Número MDL: MFCD00008498
• Código UNSPSC: 12352100
• ID de substância PubChem: 24852745
• NACRES: NA.22

Propriedades

• Ensaio: 95%
• forma: liquid
• Impurezas: 2-5% 4-methoxy-3-buten-2-one
• índice de refração: n20/D 1.454 (lit.)
• pb: 68-69 °C/14 mmHg (lit.)
• densidade: 0.885 g/mL at 25 °C (lit.)
• temperatura de armazenamento: 2-8°C
• cadeia de caracteres SMILES: 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+
• chave InChI: SHALBPKEGDBVKK-VOTSOKGWSA-N

Descrição

Descrição geral

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.

Aplicação

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

Informações de segurança

• Pictogramas: GHS02
• Palavra indicadora: Warning
• Frases de perigo: H226
• Declarações de precaução: P210 - P233 - P240 - P241 - P242 - P243
• Classificações de perigo: Flam. Liq. 3
• Código de classe de armazenamento: 3 - Flammable liquids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): 138.2 °F - closed cup
• Ponto de fulgor (°C): 59 °C - closed cup
• Equipamento de proteção individual: Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)