Consentement d'utilisation des Cookies

J'accepte Notre site sauvegarde des traceurs textes (cookies) sur votre appareil afin de vous garantir de meilleurs contenus et à des fins de collectes statistiques.Vous pouvez désactiver l'usage des cookies en changeant les paramètres de votre navigateur. En poursuivant votre navigation sur notre site sans changer vos paramètres de navigateur vous nous accordez la permission de conserver des informations sur votre appareil.

54125-02-9 - 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, 97% - Danishefsky's diene - L14672 - Alfa Aesar

L14672 1-Methoxy-3-trimethylsiloxy-1,3-butadiene, 97%

Numéro CAS
54125-02-9
Synonymes
Danishefsky's diene

Dimensions Prix ($) Quantité Disponibilité
1g 62,62
5g 222,48
Ajouter au panier Ajouter au devis en vrac Afficher l'article

1-Methoxy-3-trimethylsiloxy-1,3-butadiene, 97%

MDL
MFCD00008498

Propriétés chimiques

Formule
C8H16O2Si
Poids formulaire
172.30
Point d'ébullition
68-69°/14mm
Point d'éclair
45°(113°F)
Densité
0.890
Indice de réfraction
1.4550
Sensibilité
Moisture Sensitive
Solubilité
Miscible with most organic solvents. Immiscible with water.

Applications

1-Methoxy-3-trimethylsiloxy-1,3-butadiene is employed as a reagent in Mannich-Michael reaction for the synthesis of piperidinones and enaminones. As Diels-Alder diene, it is used in the synthesis of pyridones and pyranones, sulfone analogues of griseofulvin (sulfogriseofulvins) and 4H-1-aminopyrroles and 4, 5H-pyrazoles.

Notes

Moisture sensitive. Store in cool place. Incompatible with strong oxidizing agents and strong acids.

Références bibliographiques

High purity grade.

Oxygen-functionalized diene, useful for the regiospecific introduction of cyclohexanone or cyclohexenone groupings by cycloaddition with dienophiles: J. Am. Chem. Soc., 96, 7807 (1974); 100, 6536, 7098 (1978). Review: Acc. Chem. Res., 14, 400 (1981); review of cycloaddition reactions of silyloxydienes: Synthesis, 85 (1983); example and discussion: Org. Synth. Coll., 7, 312 (1990):

An improved procedure for the conversion of the initial adducts to enones involves treatment with TMS-OTf: J. Org. Chem., 55, 3693 (1990).

For cycloaddition to phenyl vinyl sulfone, see: J. Org. Chem., 48, 4986 (1983). Details have been given for the addition to a cyclic vinyl sulfone: Org. Synth. Coll., 8, 38 (1993).

The diene also undergoes cycloaddition reactions with heterodienophiles. Thus addition to carbonyl groups gives 2,3-dihydro--pyrones: J. Am. Chem. Soc., 104, 358 (1982); Heterocycles, 32, 273 (1991). See also Tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyl-3,5-octanedionato)­europium(III), 33541. For asymmetric Diels-Alder reaction with aldehydes, mediated by a chiral Lewis acid derived from BINOL ((R)-(+)-1,1'-Bi(2-naphthol)­, L08305) and Ti(O-i-Pr)4, see: J. Org. Chem., 60, 5998 (1995):

Reaction with imines in the presence of ZnCl2 leads to 4-oxotetrahydropyridines: Tetrahedron Lett., 23, 3739 (1982). For an example in synthesis of the manzamine marine alkaloids, see: J. Org. Chem., 57, 5741 (1992); J. Am. Chem. Soc., 117, 2363 (1995). For enantioselective asymmetric Diels-Alder reaction with an imine catalyzed by a BINOL boron Lewis acid, see: Tetrahedron, 49, 1749 (1993). For aza Diels-Alder reactions with imines in water under neutral conditions, see: Chem. Commun., 574 (2003).

For cycloaddition to Fullerene powder, 39722, see: J. Org. Chem., 60, 6353 (1995).

Choi, J.; Park, H.; Yoo, H. J.; Kim, S.; Sorensen, E. J.; Lee, C. Tandem Diels-Alder and Retro-Ene Reactions of 1-Sulfenyl- and 1-Sulfonyl-1,3-dienes as a Traceless Route to Cyclohexenes. J. Am. Chem. Soc. 2014, 136 (28), 9918-9921.

Kuttruff, C. A.; Geiger, S.; Cakmak, M.; Mayer, P.; Trauner, D. An Approach to Aminonaphthoquinone Ansamycins Using a Modified Danishefsky Diene. Org. Lett. 2012, 14 (4), 1070-1073.

Mentions de danger et de prudence du SGH

Mentions de danger (UE): H226

Flammable liquid and vapour.

Mentions de prudence: P210-P280-P240-P241-P233-P242-P243-P303+P361+P353-P403+P235-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. Keep container tightly closed. Use only non-sparking tools. Take precautionary measures against static discharge. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. Store in a well-ventilated place. Keep cool. Dispose of contents/container in accordance with local/regional/national/international regulations.

Autres références

Merck
14,6001
Beilstein
1616761
Classe de danger
3
Groupe d'emballage
III
Code tarifaire harmonisé
2931.90
TSCA
No

Recommandé

Consulté récemment

Produits chimiques

Sciences de la vie

Métaux et matériaux

Catalyseurs

Analytique et matériel de laboratoire