CAS 54125-02-9|1-甲氧基-3-三甲基硅氧基-1,3-丁二烯|1-Methoxy-3-trimethylsiloxy-1,3-butadiene|Danishefsky's diene|danishefsky's diene|{[(3E)-4-methoxybuta-1,3-dien-2-yl]oxy}trimethylsilane|<i>trans</i...

General Information

Structure

Molecular Formula

C₈H₁₆O₂Si

Molecular Mass

172.29694

Exact Mass

172.09195628

Charge

InChI

InChI=1S/C8H16O2Si/c1-8(6-7-9-2)10-11(3,4)5/h6-7H,1H2,2-5H3

InChIKey

SHALBPKEGDBVKK-UHFFFAOYSA-N

Canonic Smiles

CO/C=C/C(=C)O[Si](C)(C)C

Isomeric Smiles

O(/C=C/C(=C)O[Si](C)(C)C)C

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

1.6023

LogD (pH = 7.4)

1.6023

Log P

1.6023

Molar Refractivity

45.0415

Polarizability

19.297256

Polar Surface Area

18.46

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

Synonyms

1-甲氧基-3-三甲基硅氧基-1,3-丁二烯1-Methoxy-3-trimethylsiloxy-1,3-butadieneDanishefsky's dienetrans-1-Methoxy-3-trimethylsilyloxy-1,3-butadiene(E)-1-Methoxy-3-trimethylsilyloxy-1,3-butadieneKitahara dieneDanishefsky's dieneDanishefsky’s dienetrans-1-Methoxy-3-trimethylsiloxy-1,3-butadieneDanishefsky 二烯反-1-甲氧基-3-(三甲基硅氧基)-1,3-丁二烯

IUPAC Traditional name

danishefsky's diene

IUPAC name

{[(3E)-4-methoxybuta-1,3-dien-2-yl]oxy}trimethylsilane [(4-methoxybuta-1,3-dien-2-yl)oxy]trimethylsilane

Names and Identifiers

Registration numbers

CAS Number

Wikipedia Title

Chemspider ID

PubChem CID

PubChem SID

1622211912488397724852745

Beilstein Number

MDL Number

Merck Index

EC Number

Registration numbers

Properties

Safety Information

S23,S24/25

2-8°C

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Wikipedia

Danishefsky's_diene

Sigma Aldrich

212830

Application
Funtionalized Diels-Alder diene1,2
Packaging
1, 5 g in ampule

65368

Other Notes
Versatile electron rich diene for Diels-Alder reactions1,2,3,4

Molecule Details

References

PubChem Literature

From Data Sources

• 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):

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

danishefsky's diene

IUPAC name

{[(3E)-4-methoxybuta-1,3-dien-2-yl]oxy}trimethylsilane [(4-methoxybuta-1,3-dien-2-yl)oxy]trimethylsilane

Registration numbers

CAS Number

Wikipedia Title

Chemspider ID

PubChem CID

PubChem SID

1622211912488397724852745

Beilstein Number

MDL Number

Merck Index

EC Number

Molecule Details

212830

Application
Funtionalized Diels-Alder diene1,2
Packaging
1, 5 g in ampule

65368

Other Notes
Versatile electron rich diene for Diels-Alder reactions1,2,3,4

References

PubChem Literature

From Data Sources

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

• 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).

• High purity grade.

Bioactivity

PubChem BioAssay

Properties

Safety Information

S23,S24/25

2-8°C

Molecule

ID:126864