283754
2(5H)-Furanone
98%
Synonym(s):
γ-Crotonolactone, 2-Buten-1,4-olide
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About This Item
Empirical Formula (Hill Notation):
C4H4O2
CAS Number:
Molecular Weight:
84.07
Beilstein/REAXYS Number:
383585
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
98%
form
liquid
refractive index
n20/D 1.469 (lit.)
bp
86-87 °C/12 mmHg (lit.)
mp
4-5 °C (lit.)
density
1.185 g/mL at 25 °C (lit.)
functional group
ester
storage temp.
2-8°C
SMILES string
O=C1OCC=C1
InChI
1S/C4H4O2/c5-4-2-1-3-6-4/h1-2H,3H2
InChI key
VIHAEDVKXSOUAT-UHFFFAOYSA-N
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General description
Chiral urea compounds catalyzed hetero-Michael addition reaction of 2(5H)-furanone (γ-crotonolactone) to pyrrolidine. The quorum sensing inhibition activity by 2(5H)-furanone was studied using bioindicator strains.
Application
2(5H)-Furanone (γ-Crotonolactone) has been used in:
- synthesis of (+)-L-733,060, (+)-CP-99,994 and (2S,3R)-3-hydroxypipecolic acid
- synthesis of 5-substituted 2(5H) furanones (γ-butenolides) via direct aldol reaction with aromatic aldehydes catalyzed by bifunctional aminothiourea and aminosquaramide organocatalysts
- Michael addition reactions for synthesis of lignans
- three-component Michael-Aldol reactions with an aldehyde anda thiolate or carbanion
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
213.8 °F - closed cup
flash_point_c
101 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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Chiral urea compounds 10a-g were synthesized as catalysts for conjugate addition of pyrrolidine (2) to gamma-crotonolactone (3). In the presence of a catalytic amount of the chiral ureas, this hetero-Michael reaction was greatly accelerated. Asymmetric induction was observed with the
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