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4-methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid - CAS 212578-38-6

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Category
Main Product
Product Name
4-methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
Catalog Number
212578-38-6
Synonyms
4-Methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
CAS Number
212578-38-6
Molecular Weight
193.2
Molecular Formula
C10 H11 N O3
COA
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MSDS
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Canonical SMILES
CN1CC(OC2=CC=CC=C21)C(=O)O
InChI
InChI=1S/C10H11NO3/c1-11-6-9(10(12)13)14-8-5-3-2-4-7(8)11/h2-5,9H,6H2,1H3,(H,12,13)
InChIKey
SSVIRLKDUUXSTR-UHFFFAOYSA-N
Structure
CAS 212578-38-6 4-methyl-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid
Specification
Purity
95%
Boiling Point
376.346ºC at 760 mmHg
Density
1.283g/cm3
Reference Reading
1.Influence of chirality of the preceding acyl moiety on the cis/trans ratio of the proline peptide bond.
Breznik M1, Grdadolnik SG, Giester G, Leban I, Kikelj D. J Org Chem. 2001 Oct 19;66(21):7044-50.
We report that the cis/trans ratio of the proline peptide bond can be strongly influenced by the chirality of the acyl residue preceding proline. Acyl moieties derived from (2S)-2,6-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-2-carboxylic acid (8) and (2R)-3-methoxy-2-methyl-2-(4-methyl-2-nitrophenoxy)-3-oxopropanoic acid (5) in acyl-Pro molecules influence isomerization of the proline peptide bond constraining the omega dihedral angle to the trans orientation. Structures of benzyl (2S)-1-([(2S)-2,6-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-2-yl]carbonyl)-2-pyrrolidinecarboxylate (3) derived from 2D (1)H NMR conformational analysis and crystallographic data exhibit only the trans conformation of proline peptide bond. On the other hand the diastereomer 4, which contains an (R) acyl moiety, exhibits two sets of signals in (1)H NMR spectra. The signals were assigned to trans (72%) and cis (28%) conformers. Crystallographic analysis of 4 showed that only the cis conformation is present in the crystalline state.
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