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122068

Sigma-Aldrich

trans-4-Methoxy-3-buten-2-one

technical grade, 90%

Synonym(s):

(E)-4-Methoxy-3-buten-2-one

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About This Item

Linear Formula:
CH3OCH=CHCOCH3
CAS Number:
51731-17-0
Molecular Weight:
100.12
Beilstein:
2070991
EC Number:
257-364-0
MDL number:
MFCD00008778
UNSPSC Code:
12352100
PubChem Substance ID:
24847477
NACRES:
NA.22

grade

technical grade

Assay

90%

refractive index

n20/D 1.468 (lit.)

bp

200 °C (lit.)

density

0.982 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

[H]\C(OC)=C(\[H])C(C)=O

InChI

1S/C5H8O2/c1-5(6)3-4-7-2/h3-4H,1-2H3/b4-3+

InChI key

VLLHEPHWWIDUSS-ONEGZZNKSA-N

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General description

trans-4-Methoxy-3-buten-2-one acts as substrate and undergoes zinc triflate-catalyzed Mukaiyama-Michael reaction with 3-TBSO-substituted vinyldiazoacetate to yield functionalized 3-keto-2-diazoalkanoates.

Application

trans-4-Methoxy-3-buten-2-one was used as starting reagent for enantioselective total synthesis of (-)-epibatidine.

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

145.4 °F - closed cup

Flash Point(C)

63 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Bifunctional thiourea-catalyzed enantioselective double Michael reaction of ?, d-unsaturated ?-ketoester to nitroalkene: asymmetric synthesis of (-)-epibatidine.
Hoashi Y, et al.
Tetrahedron Letters, 45(50), 9185-9188 (2004)
Yu Liu et al.
Organic letters, 12(19), 4304-4307 (2010-09-03)
Enedione-diazoesters formed from 3-TBSO-2-diazo-3-butenoates undergo base-catalyzed pericyclization that with dinitrogen extrusion and methyl migration provide a novel and efficient route to 2-carboalkoxyresorcinols. Intercepting the intermediate enolate anion with methyl vinyl ketone leads to the corresponding 4-substituted 2-carboalkoxyresorcinol and suggests generalization

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