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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%

CAS Number
54125-02-9
Synonyms
Danishefsky's diene

Size Price ($) Quantity Availability
1g 62.62
5g 222.48
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1-Methoxy-3-trimethylsiloxy-1,3-butadiene, 97%

MDL
MFCD00008498

Chemical Properties

Formula
C8H16O2Si
Formula Weight
172.30
Boiling Point
68-69°/14mm
Flash Point
45°(113°F)
Density
0.890
Refractive Index
1.4550
Sensitivity
Moisture Sensitive
Solubility
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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226

Flammable liquid and vapour.

Precautionary Statements: 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.

Other References

Merck
14,6001
Beilstein
1616761
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
No

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