オキサゾリジン
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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/05/12 16:49:31」(JST)
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| Oxazolidine |
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| Identifiers |
| CAS number |
504-76-7 Y |
| Jmol-3D images |
Image 1 |
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| Properties |
| Molecular formula |
C3H7NO |
| Molar mass |
73.0938 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| Y (verify) (what is: Y/N?) |
| Infobox references |
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An Oxazolidine is a five-membered ring compound consisting of three carbons, a nitrogen, and an oxygen. The oxygen and NH are the 1 and 3 positions, respectively. In oxazolidine derivatives, there is always a carbon between the oxygen and the nitrogen (or it would be an isoxazolidine).[1][2] All of the carbons in oxazolidines are reduced (compare to oxazole and oxazoline). Some of their derivatives, the oxazolidinediones, are used as anticonvulsants.
Contents
- 1 Bisoxazolidines
- 2 Isoxazolidines
- 3 See also
- 4 References
Bisoxazolidines
Bisoxazolidines are chemical compounds that contain two oxazolidine rings, they are used as performance modifiers in polyurethane coatings and paints. The rings hydrolyze in the presence of moisture to give amine and hydroxyl groups, these can then react with diisocyanates to form a coating.[3] The use of a bisoxazolidine in a polyurethane systems can prevent the unwanted reaction between isocyanate and moisture resulting in coating defects, a result of carbon dioxide release. This moisture triggered curing route is preferential to moisture cure.
The choice of linker between the two oxazolidine rings has a large impact on the performance when used to cure isocyanates. A rigid linker group increases a polyurethanes toughness. A flexible linker group imparts flexibility and increases elongation of a coating. These differences are the reason why bisoxazolidines are used to enhance the performance of polyurethane systems.
Isoxazolidines
In an isoxazolidine nitrogen and oxygen occupy positions 1 and 2 in the ring:
It is the saturated relative of Isoxazole.
See also
- Imidazole, an analog with the oxygen replaced by a nitrogen.
- Thiazole, an analog with the oxygen replaced by a sulfur.
- Benzoxazole, where the oxazole is fused to another aromatic ring.
- Pyrrole, an analog without the oxygen atom.
- Furan, an analog without the nitrogen atom.
- Oxazoline, which has only one double bond reduced.
- Oxazolidinedione, which has two in-cycle keto groups (a carbamate and a lactam).
- Oxazolidinone, which has an in-cycle carbamate.
References
- ^ "SID 3881507 -- PubChem Substance Summary". The PubChem Project. United States National Center for Biotechnology Information. Retrieved 13 December 2005.
- ^ Dr Neil G Carter OXAZOLIDINE DILUENTS: REACTING FOR THE ENVIRONMENT Industrial Copolymers Limited
- ^ Emission control chembytes e-zine 2001.
English Journal
- Atropo- and Diastereoselective Construction of Tetracyclic Biphenylazepinium Salts Derived from Aminoalcohols: Use as Catalysts in Enantioselective Asymmetric Epoxidation.
- Bulman Page PC1, Pearce CA1, Chan Y1, Parker P2, Buckley BR2, Rassias GA3, Elsegood MR2.
- The Journal of organic chemistry.J Org Chem.2015 Aug 21;80(16):8036-45. doi: 10.1021/acs.joc.5b01157. Epub 2015 Aug 3.
- A range of new biphenylazepinium salt organocatalysts effective for asymmetric epoxidation has been developed incorporating an additional substituted oxazolidine ring, and providing improved enantiocontrol in alkene epoxidation over the parent structure. Starting from enantiomerically pure aminoalco
- PMID 26204427
- Cross-Aldol Reaction of Isatin with Acetone Catalyzed by Leucinol: A Mechanistic Investigation.
- Kabeshov MA1,2, Kysilka O3, Rulíšek L4, Suleimanov YV5, Bella M6, Malkov AV7, Kočovský P8,9.
- Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2015 Aug 17;21(34):12026-33. doi: 10.1002/chem.201500536. Epub 2015 Jul 6.
- Comprehensive mechanistic studies on the enantioselective aldol reaction between isatin (1 a) and acetone, catalyzed by L-leucinol (3 a), unraveled that isatin, apart from being a substrate, also plays an active catalytic role. Conversion of the intermediate oxazolidine 4 into the reactive syn-e
- PMID 26147182
- Weak C-H...O and C-H...π hydrogen bonds and π-π stacking interactions in a series of four N'-[(E)-(aryl)methylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazides.
- Nogueira TC1, Pinheiro AC1, Wardell JL1, Souza MV1, Abberley JP2, Harrison WT2.
- Acta crystallographica. Section C, Structural chemistry.Acta Crystallogr C Struct Chem.2015 Aug 1;71(Pt 8):647-52. doi: 10.1107/S2053229615012450. Epub 2015 Jul 7.
- Oxazolidin-2-ones are widely used as protective groups for 1,2-amino alcohols and chiral derivatives are employed as chiral auxiliaries. The crystal structures of four differently substituted oxazolidinecarbohydrazides, namely N'-[(E)-benzylidene]-N-methyl-2-oxo-1,3-oxazolidine-4-carbohydrazide, C12
- PMID 26243408
Japanese Journal
- SYNTHESIS AND CRYSTAL STRUCTURE OF (4S)-4-BENZYL-3-(4,5-DIMETHOXY-2-METHYLBENZOYL)-2,2-DIMETHYL-1,3-OXAZOLIDINE (Dedicated to Professor Isao Kuwajima on the occasion of his 77th birthday)
- Chrzanowska Maria,Meissner Zofia,Chrzanowska Joanna M. [他]
- Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 90(1), 730-739, 2015-01-01
- NAID 40020330673
- Crystal Structure of <font size=-1>L</font>-Isoleucine N-Carboxy Anhydride
- INADA Aya,KANAZAWA Hitoshi,UEKUSA Hidehiro
- X-ray Structure Analysis Online 31(0), 17-18, 2015
- … The title compound, (4S)-4-[(2S)-butan-2-yl]-1,3-oxazolidine-2,5-dione, C7H11NO3 was synthesized and the crystal structure was determined by the single-crystal X-ray diffraction method at 123 K. … The oxazolidine ring in this compound is planar with a maximum deviation of 0.037(4)Å. …
- NAID 130004953664
- CHIRAL OXAZOLIDINE CATALYST FOR ASYMMETRIC SYNTHESIS
- Nakano Hiroto,Okuyama Yuko,Kwon Eunsang
- Heterocycles : an international journal for reviews and communications in heterocyclic chemistry 89(1), 1-26, 2014-01-01
- NAID 40019938175
Related Links
- The Incozol series of oxazolidines consists of a range of mono and bis-oxazolidines, which hydrolyse on exposure to moisture yielding reactive amine and hydroxyl functionalities.
- Structure, properties, spectra, suppliers and links for: Oxazolidine, 504-76-7. ... Predicted data is generated using the US Environmental Protection Agency’s EPISuite Log Octanol-Water Partition Coef (SRC): Log Kow ...