165123
Diethyl 1,3-acetonedicarboxylate
96%
Synonym(s):
Diethyl 3-oxoglutarate
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About This Item
Linear Formula:
CO(CH2COOC2H5)2
CAS Number:
Molecular Weight:
202.20
Beilstein/REAXYS Number:
640146
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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assay
96%
form
liquid
refractive index
n20/D 1.440 (lit.)
bp
250 °C (lit.)
density
1.113 g/mL at 25 °C (lit.)
functional group
ester
SMILES string
CCOC(=O)CC(=O)CC(=O)OCC
InChI
1S/C9H14O5/c1-3-13-8(11)5-7(10)6-9(12)14-4-2/h3-6H2,1-2H3
InChI key
ZSANYRMTSBBUCA-UHFFFAOYSA-N
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Application
Diethyl 1,3-acetonedicarboxylate was used in the synthesis of novel pyrido[4,3,2-de]quinoline, isoquinolino[6,5,4,3-cde] quinoline and pyrazomycin. It was used as starting reagent in the synthesis of (±)-thienamycin, potent β-lactam antibiotic.
Storage Class
10 - Combustible liquids
wgk_germany
WGK 3
flash_point_f
159.8 °F - closed cup
flash_point_c
71 °C - closed cup
ppe
Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)
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A synthesis of the pyrazomycins.
S De Bernardo et al.
The Journal of organic chemistry, 41(2), 287-290 (1976-01-23)
A practical synthesis of (?)-thienamycin.
Melillo DG, et al.
Tetrahedron Letters, 21(29), 2783-2786 (1980)
Q Ding et al.
Anti-cancer drug design, 15(2), 99-108 (2000-07-20)
A series of novel pyrido[4,3,2-de]quinoline and isoquinolino[6,5,4,3-cde] quinoline compounds was synthesized and evaluated for cytotoxicity in the National Cancer Institute developmental therapeutics program. The tricyclic compound 7 was synthesized by the cyclization of 3,4-diamino-1,2dimethoxybenzene with diethyl 1,3-acetonedicarboxylate. Oxidation of monochloropyrido[4,3,2-de]quinoline
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