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

• Catalog No.: L14672
• CAS Number: 54125-02-9
• M. F.: C8H16O2Si
• M. W.: 172.29694
• Purity: 98+%

SYNONYMS

• Title: 1-甲氧基-3-三甲基硅氧基-1,3-丁二烯
• IUPAC name: {[(3E)-4-methoxybuta-1,3-dien-2-yl]oxy}trimethylsilane
• IUPAC Traditional name: danishefsky's diene
• Synonyms: Danishefsky's diene

DATABASE IDS

• MDL Number: MFCD00008498
• Merck Index: 146001
• CAS Number: 54125-02-9
• EC Number: 000-000-0
• Beilstein Number: 1616761

PROPERTIES

• Purity: 98+%
• Boiling Point: 68-69°C/14mm
• Density: 0.890
• Flash Point: 45°C(113°F)
• Refractive Index: 1.4550
• GHS Hazard statements: H226
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A
• Risk Statements: 10
• Storage Warning: Moisture Sensitive
• TSCA Listed: 否
• Hazard Class: 3
• UN Number: UN1993
• Packing Group: III

REFERENCES

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