468975
Benzyl (S)-(−)-4-oxo-2-azetidinecarboxylate
97%
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About This Item
Empirical Formula (Hill Notation):
C11H11NO3
CAS Number:
Molecular Weight:
205.21
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Product Name
Benzyl (S)-(−)-4-oxo-2-azetidinecarboxylate, 97%
InChI
1S/C11H11NO3/c13-10-6-9(12-10)11(14)15-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,12,13)/t9-/m0/s1
SMILES string
O=C1C[C@H](N1)C(=O)OCc2ccccc2
InChI key
WGLLBHSIXLWVFU-VIFPVBQESA-N
assay
97%
optical activity
[α]21/D −44°, c = 3.3 in chloroform
mp
137-140 °C (lit.)
functional group
ester
phenyl
Quality Level
Related Categories
Application
Benzyl (S)-(-)-4-oxo-2-azetidinecarboxylate may be used in the preparation of its N-acetyl derivative, which can be a potential candidate as solid electrolyte interphase (SEI)-forming additive in lithium-ion batteries.
Important building block for the synthesis of NMDA receptor antagonists, 3-alkyl-L-aspartic acids, and orally active β-lactam inhibitors.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Computational screening of lactam molecules as solid electrolyte interphase forming additives in lithium-ion batteries.
Han YK, et al.
Current Applied Physics, 14(6), 897-900 (2014)
Baldwin, J.E. et al.
Tetrahedron, 51, 11581-11581 (1995)
Hanessian, S. et al.
Synlett, 33-33 (1992)
P E Finke et al.
Journal of medicinal chemistry, 38(13), 2449-2462 (1995-06-23)
The stereospecific synthesis of several 4-[(4-carboxyphenyl)oxy]- 3,3-dialkyl-1-[[(1-phenylalkyl)-amino]carbonyl]azetidin-2-on es 3 is described in which the C-3 alkyl groups were varied from methyl to butyl as well as allyl, benzyl and methoxymethyl. The structure-activity relations for these compounds are discussed in terms
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