Substance
ID:737415
Names and Identifiers
IUPAC name
{[(3E)-4-methoxybuta-1,3-dien-2-yl]oxy}trimethylsilane
Synonyms
1-Methoxy-3-trimethylsiloxy-1,3-butadieneDanishefsky's diene1-甲氧基-3-三甲基硅氧基-1,3-丁二烯
IUPAC Traditional name
danishefsky's diene
Registration numbers
CAS Number
Beilstein Number
MDL Number
Merck Index
EC Number
Properties
Safety Information
GHS Precautionary statements
P210-P241-P280-P303+P361+P353-P403+P235-P501A
Hazard Class
3
UN Number
UN1993
Packing Group
III
Storage Warning
Moisture Sensitive
Risk Statements
10
GHS Pictograms
Flammable gases, category 1
Flammable aerosols, categories 1,2
Flammable liquids, categories 1,2,3
Self-reactive substances and mixtures, Types B,C,D,E,F
Pyrophoric liquids, category 1
Pyrophoric solids, category 1
Self-heating substances and mixtures
Substances and mixtures, which in contact with water, emit flammable gases, categories 1,2,3
Organic peroxides, Types B,C,D,E,F
TSCA Listed
否
GHS Hazard statements
H226
Physical Property
Flash Point
45°C(113°F)
Refractive Index
1.4550
Density
0.890
Boiling Point
68-69°C/14mm
Product Information
Purity
98+%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• For cycloaddition to Fullerene powder, 39722, see: J. Org. Chem., 60, 6353 (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).
• 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):
• 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):
