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'''Tetrahydropyran''' (THP) is the [[organic compound]] consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. The compound is a colourless volatile liquid, but is obscure. Derivatives of tetrahydropyran are, however, more common. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and [[dihydropyran]] are common intermediates in [[organic synthesis]]. Furthermore, a tetrahydropyran ''ring system'', i.e., five carbon atoms and an oxygen, is the core of [[pyranose]] sugars, such as [[glucose]]. In gas phase, the THP exists in its lowest energy Cs symmetry chair conformation<ref>{{Cite journal|title = A dynamical (e,2e) investigation of the structurally related cyclic ethers tetrahydrofuran, tetrahydropyran, and 1,4-dioxane|url = http://scitation.aip.org/content/aip/journal/jcp/139/3/10.1063/1.4813237|journal = The Journal of Chemical Physics|date = 2013-07-21|issn = 0021-9606|pages = 034306|volume = 139|issue = 3|doi = 10.1063/1.4813237|first = J. D.|last = Builth-Williams|first2 = S. M.|last2 = Bellm|first3 = L.|last3 = Chiari|first4 = P. A.|last4 = Thorn|first5 = D. B.|last5 = Jones|first6 = H.|last6 = Chaluvadi|first7 = D. H.|last7 = Madison|first8 = C. G.|last8 = Ning|first9 = B.|last9 = Lohmann}}</ref> |
'''Tetrahydropyran''' (THP) is the [[organic compound]] consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. The compound is a colourless volatile liquid, but is obscure. Derivatives of tetrahydropyran are, however, more common. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and [[dihydropyran]] are common intermediates in [[organic synthesis]]. Furthermore, a tetrahydropyran ''ring system'', i.e., five carbon atoms and an oxygen, is the core of [[pyranose]] sugars, such as [[glucose]]. In gas phase, the THP exists in its lowest energy Cs symmetry chair conformation.<ref>{{Cite journal|title = A dynamical (e,2e) investigation of the structurally related cyclic ethers tetrahydrofuran, tetrahydropyran, and 1,4-dioxane|url = http://scitation.aip.org/content/aip/journal/jcp/139/3/10.1063/1.4813237|journal = The Journal of Chemical Physics|date = 2013-07-21|issn = 0021-9606|pages = 034306|volume = 139|issue = 3|doi = 10.1063/1.4813237|first = J. D.|last = Builth-Williams|first2 = S. M.|last2 = Bellm|first3 = L.|last3 = Chiari|first4 = P. A.|last4 = Thorn|first5 = D. B.|last5 = Jones|first6 = H.|last6 = Chaluvadi|first7 = D. H.|last7 = Madison|first8 = C. G.|last8 = Ning|first9 = B.|last9 = Lohmann}}</ref> |
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==Preparation== |
==Preparation== |
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{{Authority control}} |
{{Authority control}} |
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[[Category:Protecting groups]] |
[[Category:Protecting groups]] |
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[[Category:Ether solvents]] |
[[Category:Ether solvents]] |
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Revision as of 07:07, 24 November 2015
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| Names | |||
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| IUPAC name
Oxane
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| Other names
Tetrahydropyran,
Oxacyclohexane | |||
| Identifiers | |||
3D model (JSmol)
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| ChEBI | |||
| ChemSpider | |||
| DrugBank | |||
| ECHA InfoCard | 100.005.048 | ||
| KEGG | |||
PubChem CID
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| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| C5H10O | |||
| Molar mass | 86.13 g/mol | ||
| Density | 0.880 g/cm3 | ||
| Melting point | −45 °C (−49 °F; 228 K) | ||
| Boiling point | 88 °C (190 °F; 361 K) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Tetrahydropyran (THP) is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom. The compound is a colourless volatile liquid, but is obscure. Derivatives of tetrahydropyran are, however, more common. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. Furthermore, a tetrahydropyran ring system, i.e., five carbon atoms and an oxygen, is the core of pyranose sugars, such as glucose. In gas phase, the THP exists in its lowest energy Cs symmetry chair conformation.[1]
Preparation
One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[2]
Reactions
In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols.[3][4] Reaction of the alcohol with dihydropyran forms a tetrahydropyranyl ether, protecting the alcohol from a variety of reactions. The alcohol can later be restored readily by acidic hydrolysis with formation of 5-hydroxypentanal.
See also
- Tetrahydrofuran (THF)
- Pyran
References
- ^ Builth-Williams, J. D.; Bellm, S. M.; Chiari, L.; Thorn, P. A.; Jones, D. B.; Chaluvadi, H.; Madison, D. H.; Ning, C. G.; Lohmann, B. (2013-07-21). "A dynamical (e,2e) investigation of the structurally related cyclic ethers tetrahydrofuran, tetrahydropyran, and 1,4-dioxane". The Journal of Chemical Physics. 139 (3): 034306. doi:10.1063/1.4813237. ISSN 0021-9606.
- ^ D. W. Andrus; John R. Johnson (1955). "Tetrahydropyran". Organic Syntheses
{{cite journal}}: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 3, p. 794. - ^ R. A. Earl L. B. Townsend (1990). "Methyl 4-Hydroxy-2-butynoate". Organic Syntheses; Collected Volumes, vol. 7, p. 334.
- ^ Arthur F. Kluge (1990). "Diethyl [(2-Tetrahydropyranyloxy)methyl]phosphonate". Organic Syntheses; Collected Volumes, vol. 7, p. 160.
| Authority control databases: National |
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