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504-77-8 | 4,5-dihydrooxazole
CAS No: 504-77-8 Catalog No: AG00DF3G MDL No:MFCD00792480
Product Description
Catalog Number:
AG00DF3G
Chemical Name:
4,5-dihydrooxazole
CAS Number:
504-77-8
MDL Number:
MFCD00792480
IUPAC Name:
4,5-dihydro-1,3-oxazole
InChI:
InChI=1S/C3H5NO/c1-2-5-3-4-1/h3H,1-2H2
InChI Key:
IMSODMZESSGVBE-UHFFFAOYSA-N
EC Number:
208-000-4
UNII:
31TB4J57Y5
Properties
Complexity:
50.9
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
71.037g/mol
Formal Charge:
0
Heavy Atom Count:
5
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
71.079g/mol
Monoisotopic Mass:
71.037g/mol
Rotatable Bond Count:
0
Topological Polar Surface Area:
21.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.2
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| Stereoselective synthesis of L-threo-sphingosine, L-threo-sphinganine, D-threo-sphingosine, and D-threo-sphinganine via oxazoline formation and olefin cross-metathesis; potent protein kinase C inhibitor analogues. | Archives of pharmacal research 20070201 |
| Tripodal borate ligands from tris(dimethylamino)borane: the first synthesis of a chiral tris(methimazolyl)borate ligand, and the crystal structure of a single diastereomer pseudo-C3-symmetric Ru(II) complex. | Dalton transactions (Cambridge, England : 2003) 20070128 |
| Screening of a modular sugar-based phosphite-oxazoline ligand library in asymmetric Pd-catalyzed heck reactions. | Chemistry (Weinheim an der Bergstrasse, Germany) 20070101 |
| Shaping and enforcing coordination spheres: the implications of C3 and C1 chirality in the coordination chemistry of 1,1,1-tris(oxazolinyl)ethane ('trisox'). | Chemistry (Weinheim an der Bergstrasse, Germany) 20070101 |
| [1,6-Anhydro-N-Acetyl- beta-D-glucosamine in oligosaccharide synthesis: II. synthesis of a spacered Ley tetrasaccharide]. | Bioorganicheskaia khimiia 20070101 |
| One-step synthesis of oxazoline and dihydrooxazine libraries. | Journal of combinatorial chemistry 20070101 |
| Using a tripod as a chiral chelating ligand: chemical exchange between equivalent molecular structures in palladium catalysis with 1,1,1-tris(oxazolinyl)ethane ('trisox'). | Chemistry (Weinheim an der Bergstrasse, Germany) 20070101 |
| Synthesis and metal complexes of chiral c(2)-symmetric diamino-bisoxazoline ligands. | Chemistry (Weinheim an der Bergstrasse, Germany) 20070101 |
| Stereochemical consequences of threefold symmetry in asymmetric catalysis: distorting C3 Chiral 1,1,1-tris(oxazolinyl)ethanes ('trisox') in CuII Lewis acid catalysts. | Chemistry (Weinheim an der Bergstrasse, Germany) 20070101 |
| The nature of the chemical bond in linear three-body systems: from i3- to mixed chalcogen/halogen and trichalcogen moieties. | Bioinorganic chemistry and applications 20070101 |
| Studies on enantioselective allylic oxidation of olefins using peresters catalyzed by Cu(I)-complexes of chiral pybox ligands. | Organic & biomolecular chemistry 20061207 |
| Endocannabinoid metabolomics: a novel liquid chromatography-mass spectrometry reagent for fatty acid analysis. | The AAPS journal 20061201 |
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| Pyridinyloxazolidines: versatile scaffolds for chiral catalyst construction. | Dalton transactions (Cambridge, England : 2003) 20061021 |
| Total synthesis of the cyclodepsipeptide apratoxin A and its analogues and assessment of their biological activities. | Chemistry (Weinheim an der Bergstrasse, Germany) 20061010 |
| Exploring alternative Zn-binding groups in the design of HDAC inhibitors: squaric acid, N-hydroxyurea, and oxazoline analogues of SAHA. | Bioorganic & medicinal chemistry letters 20060915 |
| Deflazacort for type-1 autoimmune hepatitis in a Korean girl. | Journal of Korean medical science 20060801 |
| Synthesis of N-glycan oxazolines: donors for endohexosaminidase catalysed glycosylation. | Carbohydrate research 20060724 |
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| Selective 6-endo cyclization of the acyl radicals onto the nitrogen of imine and oxazoline C-N bonds. | Journal of the American Chemical Society 20060621 |
| Synthesis and application of chiral N-heterocyclic carbene-oxazoline ligands: iridium-catalyzed enantioselective hydrogenation. | Chemistry (Weinheim an der Bergstrasse, Germany) 20060602 |
| Triruthenium carbonyl clusters derived from chiral aminooxazolines: synthesis and catalytic activity. | Dalton transactions (Cambridge, England : 2003) 20060528 |
| Glycopeptide synthesis through endo-glycosidase-catalyzed oligosaccharide transfer of sugar oxazolines: probing substrate structural requirement. | Chemistry (Weinheim an der Bergstrasse, Germany) 20060412 |
| Total synthesis and biological evaluation of halipeptins A and D and analogues. | Journal of the American Chemical Society 20060405 |
| Identification of Asp174 and Asp175 as the key catalytic residues of human O-GlcNAcase by functional analysis of site-directed mutants. | Biochemistry 20060321 |
| Theoretical study of structure, pKa, lipophilicity, solubility, absorption, and polar surface area of some centrally acting antihypertensives. | Bioorganic & medicinal chemistry 20060315 |
| Synthesis and biological evaluation of simplified mycothiazole analogues. | Bioorganic & medicinal chemistry letters 20060301 |
| Chitinase-catalyzed synthesis of alternatingly N-deacetylated chitin: a chitin-chitosan hybrid polysaccharide. | Biomacromolecules 20060301 |
| Catalytic enantioselective Friedel-Crafts/Michael addition reactions of indoles to ethenetricarboxylates. | The Journal of organic chemistry 20060120 |
| Palladium-catalyzed alkylation of aryl C-H bonds with sp3 organotin reagents using benzoquinone as a crucial promoter. | Journal of the American Chemical Society 20060111 |
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| Conformational preferences and enantiodiscrimination of phosphino-4-(1-hydroxyalkyl)oxazoline-metal-olefin complexes resulting from an OH-metal hydrogen bond. | The Journal of organic chemistry 20051125 |
| Chemoenzymatic synthesis of HIV-1 V3 glycopeptides carrying two N-glycans and effects of glycosylation on the peptide domain. | The Journal of organic chemistry 20051125 |
| Design of hydrogen bond catalysts based on a modular oxazoline template: application to an enantioselective hetero Diels-Alder reaction. | Organic letters 20051124 |
| Synthesis of 2H-1,2-benzothiazine 1,1-dioxides via heteroannulation reactions of 2-iodobenzenesulfonamide with ketone enolates under S(RN)1 conditions. | The Journal of organic chemistry 20051111 |
| Enantiodivergent, biocatalytic routes to both taxol side chain antipodes. | The Journal of organic chemistry 20051111 |
| Total synthesis of halipeptins: isolation of halipeptin D and synthesis of oxazoline halipeptin analogues. | Chemistry (Weinheim an der Bergstrasse, Germany) 20051021 |
| Three isomeric forms of hydroxyphenyl-2-oxazoline: 2-(2-hydroxyphenyl)-2-oxazoline, 2-(3-hydroxyphenyl)-2-oxazoline and 2-(4-hydroxyphenyl)-2-oxazoline. | Acta crystallographica. Section C, Crystal structure communications 20051001 |
| Some new aspects of the Boyer reaction. | Organic letters 20050915 |
| Breaking the C3-symmetry of chiral tripodal oxazolines: enantio-discrimination of chiral organoammonium ions. | The Journal of organic chemistry 20050902 |
| Nitrosation chemistry of pyrroline, 2-imidazoline, and 2-oxazoline: theoretical Curtin-Hammett analysis of retro-ene and solvent-assisted C-X cleavage reactions of alpha-hydroxy-N-nitrosamines. | The Journal of organic chemistry 20050819 |
| The development and application of chiral trisoxazolines in asymmetric catalysis and molecular recognition. | Chemical Society reviews 20050801 |
| O-GlcNAcase uses substrate-assisted catalysis: kinetic analysis and development of highly selective mechanism-inspired inhibitors. | The Journal of biological chemistry 20050708 |
| An efficient, stereocontrolled synthesis of a potent omuralide-salinosporin hybrid for selective proteasome inhibition. | Journal of the American Chemical Society 20050629 |
| Heterocyclic derivative syntheses by palladium-catalyzed oxidative cyclization-alkoxycarbonylation of substituted gamma-oxoalkynes. | The Journal of organic chemistry 20050624 |
| Lipopolymers from new 2-substituted-2-oxazolines for artificial cell membrane constructs. | Macromolecular bioscience 20050523 |
| Anthryl-substituted heterocycles as acid-sensitive fluorescence probes. | The Journal of organic chemistry 20050513 |
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| An easy approach to optically active alpha-amino phosphonic acid derivatives by chiral Zn(II)-catalyzed enantioselective amination of phosphonates. | Journal of the American Chemical Society 20050427 |
| Ortho-selective direct cross-coupling reaction of 2-aryloxazolines and 2-arylimidazolines with aryl and alkenyl halides catalyzed by ruthenium complexes. | The Journal of organic chemistry 20050415 |
| Asymmetric cyclopropanation of 2,5-dimethyl-2,4-hexadiene by copper catalysts bearing new bisoxazoline ligands. | The Journal of organic chemistry 20050415 |
| Organosilanols as catalysts in asymmetric aryl transfer reactions. | Organic letters 20050331 |
| Influence of satellite groups on telechelic antimicrobial functions of polyoxazolines. | Macromolecular bioscience 20050223 |
| Cytosporone E: racemic synthesis and preliminary antibacterial testing. | Bioorganic & medicinal chemistry 20050215 |
| Poly(oxazoline)s with telechelic antimicrobial functions. | Biomacromolecules 20050101 |
| Enzymatic synthesis of chondroitin 4-sulfate with well-defined structure. | Biomacromolecules 20050101 |
| [Synthesis and protective activity of beta-glycosides of N-acetylmuramyl-L-alanyl-D-isoglutamine with alkylalicyclic and arylaliphatic aglycons]. | Bioorganicheskaia khimiia 20050101 |
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| Formation of mononuclear and chloro-bridged binuclear copper(II) complexes of patellamide D, a naturally occurring cyclic peptide: influence of anion and solvent. | Journal of inorganic biochemistry 20041101 |
| Asymmetric hetero-Diels-Alder reactions of N-sulfinyl dienophiles using chiral bis(oxazoline)-copper(II) and -zinc(II) triflates. | The Journal of organic chemistry 20041015 |
| Synthesis and evaluation of novel oxazoline MMP inhibitors. | Bioorganic & medicinal chemistry letters 20041004 |
| Synthesis, structure, and catalytic properties of V(IV), Mn(III), Mo(VI), and U(VI) complexes containing bidentate (N, O) oxazine and oxazoline ligands. | Inorganic chemistry 20040906 |
| A C3-symmetrical chiral trisoxazoline zinc complex as a functional model for zinc hydrolases: kinetic resolution of racemic chiral esters by transesterification. | Angewandte Chemie (International ed. in English) 20040827 |
| Multielectron atom transfer reactions of perchlorate and other substrates catalyzed by rhenium oxazoline and thiazoline complexes: reaction kinetics, mechanisms, and density functional theory calculations. | Inorganic chemistry 20040628 |
| Nickel and iron complexes with oxazoline- or pyridine-phosphonite ligands; synthesis, structure and application for the catalytic oligomerisation of ethylene. | Dalton transactions (Cambridge, England : 2003) 20040521 |
| Selective oxidation of polyfunctional 2-amino-1,3-propanediol derivatives. | The Journal of organic chemistry 20040514 |
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| Catalytic asymmetric bromination and chlorination of beta-ketoesters. | Chemistry (Weinheim an der Bergstrasse, Germany) 20040503 |
| Direct catalytic asymmetric aldol reactions of pyruvates: scope and mechanism. | Organic & biomolecular chemistry 20040407 |
| Controllable enantioselective Friedel-Crafts reaction between indoles and alkylidene malonates catalyzed by pseudo-C3-symmetric trisoxazoline copperII complexes. | The Journal of organic chemistry 20040220 |
| Facile syntheses of oxazolines and thiazolines with N-acylbenzotriazoles under microwave irradiation. | The Journal of organic chemistry 20040206 |
| Theoretical insights into the role of a counterion in copper-catalyzed enantioselective cyclopropanation reactions. | Chemistry (Weinheim an der Bergstrasse, Germany) 20040206 |
| Rational design of a bimodular model system for the investigation of heterocyclization in nonribosomal peptide biosynthesis. | Chemistry & biology 20040201 |
| Corticosteroid avoidance in pediatric renal transplantation: can it be achieved? | Paediatric drugs 20040101 |
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| C2-symmetric bis(oxazolinato)lanthanide catalysts for enantioselective intramolecular hydroamination/cyclization. | Journal of the American Chemical Society 20031203 |
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| The leupyrrins: a structurally unique family of secondary metabolites from the myxobacterium Sorangium cellulosum. | Journal of natural products 20030901 |
| Oxidase domains in epothilone and bleomycin biosynthesis: thiazoline to thiazole oxidation during chain elongation. | Biochemistry 20030819 |
| Amphiphilic polymer supports for the asymmetric hydrogenation of amino acid precursors in water. | Chemistry (Weinheim an der Bergstrasse, Germany) 20030721 |
| Direct asymmetric Michael reactions of cyclic 1,3-dicarbonyl compounds and enamines catalyzed by chiral bisoxazoline-copper(II) complexes. | The Journal of organic chemistry 20030627 |
| Evaluation of chiral oxazolines for the highly enantioselective diethylzinc addition to N-(diphenylphosphinoyl) imines. | The Journal of organic chemistry 20030530 |
| A procedure for preparing oxazolines of highly unsaturated fatty acids to determine double bond positions by mass spectrometry. | Journal of lipid research 20030501 |
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| Synthesis and anti-histaminic evaluation of N-phenyl-(alkyl)-5-(dialkylamino)methyl-2-amino-2-oxazolines. | Journal of enzyme inhibition and medicinal chemistry 20030401 |
| Designing supramolecular structures from models of cyclic peptide scaffolds with heterocyclic constraints. | Journal of molecular graphics & modelling 20030301 |
| High-throughput catch-and-release synthesis of oxazoline hydroxamates. Structure-activity relationships in novel inhibitors of Escherichia coli LpxC: in vitro enzyme inhibition and antibacterial properties. | Journal of the American Chemical Society 20030212 |
| Carbonyl-ene reactions catalyzed by bis(oxazoline) copper (II) complexes proceed by a facile stepwise mechanism: DFT and ONIOM (DFT:PM3) studies. | Journal of the American Chemical Society 20030122 |
| Inhibitors of calling behavior of Plodia interpunctella. | Journal of insect science (Online) 20030101 |
| Synthesis of allylic alcohols from oxazolinyloxiranes. | The Journal of organic chemistry 20021129 |
| Coupling of bulky, electron-deficient partners in aryl amination in the preparation of tridentate bis(oxazoline) ligands for asymmetric catalysis. | The Journal of organic chemistry 20021129 |
| Dendritic oxazoline ligands in enantioselective palladium-catalyzed allylic alkylations. | The Journal of organic chemistry 20021115 |
| Aspartate 313 in the Streptomyces plicatus hexosaminidase plays a critical role in substrate-assisted catalysis by orienting the 2-acetamido group and stabilizing the transition state. | The Journal of biological chemistry 20021018 |
| Copper-catalyzed enantioselective conjugate addition of diethylzinc to acyclic enones in the presence of planar-chiral phosphaferrocene-oxazoline ligands. | Organic letters 20021017 |
| Modular synthesis of amine-functionalized oxazolines. | Organic letters 20021003 |
| Modular bis(oxazoline) ligands for palladium catalyzed allylic alkylation: unprecedented conformational behaviour of a bis(oxazoline) palladium eta3-1,3-diphenylallyl complex. | Chemistry (Weinheim an der Bergstrasse, Germany) 20020916 |
| A flat squared conformation of an ascidiacyclamide derivative caused by chiral modification of an oxazoline residue. | Biochemical and biophysical research communications 20020913 |
| Non-centrosymmetric packing of 1-D coordination networks based on chirality. | Chemical communications (Cambridge, England) 20020907 |
| Metal-induced supramolecualr chirality in an optically active polythiophene aggregate. | Chemistry (Weinheim an der Bergstrasse, Germany) 20020902 |
| The influence of ligand side chain on the enantioselectivity of Lewis acid catalyzed Diels-Alder reactions. | Chemical & pharmaceutical bulletin 20020901 |
| C2-amidoglycosylation. Scope and mechanism of nitrogen transfer. | Journal of the American Chemical Society 20020821 |
| 11-Methyl-12a-phenyl-9a,12a-dihydrophenanthro[9',10':5,6][1,4]dioxino[2,3-d]oxazole and 9a-(10-hydroxyphenanthren-9-yl)-11,12a-diphenyl-9a,12a-dihydrophenanthro[9',10':5,6][1,4]dioxino[2,3-d]oxazole. | Acta crystallographica. Section C, Crystal structure communications 20020801 |
| Asymmetric synthesis of a selective endothelin A receptor antagonist. | Chemical & pharmaceutical bulletin 20020801 |
| Highly enantioselective copper-bisoxazoline-catalyzed allylic oxidation of cyclic olefins with tert-butyl p-nitroperbenzoate. | Journal of the American Chemical Society 20020731 |
| Immobilized oxazoline-containing ligands in asymmetric catalysis--a review. | Bioorganic & medicinal chemistry letters 20020722 |
| Potent, novel in vitro inhibitors of the Pseudomonas aeruginosa deacetylase LpxC. | Journal of medicinal chemistry 20020704 |
| Three 2-oxazolinyl rings on one quaternary carbon atom: preparation of a novel tripodal tris(oxazolinyl) ligand and the tetrameric molecular structure of its CuI complex. | Chemical communications (Cambridge, England) 20020621 |
| Degradation of and drug release from a novel 2,2-bis(2-oxazoline) linked poly(lactic acid) polymer. | Journal of controlled release : official journal of the Controlled Release Society 20020617 |
| Metalation of 4-oxazolinyloxazole derivatives. A convenient route to 2,4-bifunctionalized oxazoles. | The Journal of organic chemistry 20020531 |
| Stereospecific beta-lithiation of oxazolinyloxiranes: synthesis of alpha,beta-epoxy-gamma-butyrolactones. | Organic letters 20020502 |
| Total synthesis of the turrianes and evaluation of the DNA-cleaving properties. | Chemistry (Weinheim an der Bergstrasse, Germany) 20020415 |
| On the intermediates in chiral bis(oxazoline)copper(II)-catalyzed enantioselective reactions--experimental and theoretical investigations. | Chemistry (Weinheim an der Bergstrasse, Germany) 20020415 |
| Synthesis and structural properties of patellamide A derivatives and their copper(II) compounds. | Chemistry (Weinheim an der Bergstrasse, Germany) 20020402 |
| Chemical synthesis of benzamide riboside. | Current medicinal chemistry 20020401 |
| Catalytic asymmetric direct alpha-amination reactions of 2-keto esters: a simple synthetic approach to optically active syn-beta-amino-alpha-hydroxy esters. | Journal of the American Chemical Society 20020320 |
| Lewis acid-catalyzed asymmetric diels-alder reactions using chiral sulfoxide ligands: chiral 2-(arylsulfinylmethyl)-1,3-oxazoline derivatives. | Chemical & pharmaceutical bulletin 20020301 |
| Mechanisms of steroid impairment of growth. | Hormone research 20020101 |
| Enantioselective hydrogenations of arylalkenes mediated by [Ir(cod) (JM-Phos) ]+ complexes. | Chemistry (Weinheim an der Bergstrasse, Germany) 20011217 |
| Biosynthesis of the thiazolylpeptide antibiotic GE2270. | The Journal of antibiotics 20011201 |
| Ru(3)(CO)(12)-catalyzed coupling reaction of sp(3) C-H bonds adjacent to a nitrogen atom in alkylamines with alkenes. | Journal of the American Chemical Society 20011107 |
| Catalyhtic asymmetric Henry reactions--a simple approach to optically active beta-nitro alpha-hydroxy esters. | Chemical communications (Cambridge, England) 20011107 |
| Proline-based P, N ligands in asymmetric allylation and the Heck reaction. | The Journal of organic chemistry 20011102 |
| Study of glycosylation with N-trichloroacetyl-D-glucosamine derivatives in the syntheses of the spacer-armed pentasaccharides sialyl lacto-N-neotetraose and sialyl lacto-N-tetraose, their fragments, and analogues. | Carbohydrate research 20011101 |
| Diastereo- and enantioselective cyclopropanation with chromium fischer carbene complexes: alkenyl oxazolines as useful achiral and chiral substrates. | Journal of the American Chemical Society 20011031 |
| Delta(2)-oxazolines-1,3 and N-acylaziridines as potential proinsecticides of carboxylic acids. V. Direct thin-layer chromatography monitoring of the metabolism in locust tissues. | Journal of chromatography. B, Biomedical sciences and applications 20010915 |
| Total synthesis of tricyclic azaspirane derivatives of tyrosine: FR901483 and TAN1251C. | Journal of the American Chemical Society 20010808 |
| Synthesis and chiroptical properties of optically active, regioregular oligothiophenes. | Organic letters 20010726 |
| Significance of asymmetric sites in choosing siderophores as deferration agents. | Journal of medicinal chemistry 20010719 |
| Synthesis, absolute configuration, and enantiomeric enrichment of a cruciferous oxindole phytoalexin, (S)-(-)-spirobrassinin, and its oxazoline analog. | The Journal of organic chemistry 20010601 |
| Enantioselective and diastereoselective Mukaiyama-Michael reactions catalyzed by bis(oxazoline) copper(II) complexes. | Journal of the American Chemical Society 20010516 |
| Optical peroxide biosensor using the electrically controlled-release technique. | Biosensors & bioelectronics 20010501 |
| Effects of amino acids and chirality for molecular folding of desoxazoline-ascidiacyclamide derivatives: X-ray crystal structures of four cyclic octapeptides including unusual amino acids, cyclo(-Ile-aThr-D-Val-Thz-)(2), cyclo(-Ala-aThr-D-Val-Thz-Ile-aThr-D-Val-Thz-), cyclo(-Val-aThr-D-Val-Thz-Ile-aThr-D-Val-Thz-), and cyclo(-Ile-aThr-Val-Thz-Ile-aThr-D-Val-Thz-). | Biopolymers 20010301 |
| Catalytic, highly enantioselective Friedel-Crafts reactions of aromatic and heteroaromatic compounds to trifluoropyruvate. A simple approach for the formation of optically active aromatic and heteroaromatic hydroxy trifluoromethyl esters. | The Journal of organic chemistry 20010209 |
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