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| Name = Tetrahydropyran |
| Name = Tetrahydropyran |
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| ImageFileL1 = Tetrahydropyran.png |
| ImageFileL1 = Tetrahydropyran.png |
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| InChI = 1/C5H10O/c1-2-4-6-5-3-1/h1-5H2 |
| InChI = 1/C5H10O/c1-2-4-6-5-3-1/h1-5H2 |
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| InChIKey = DHXVGJBLRPWPCS-UHFFFAOYAV |
| InChIKey = DHXVGJBLRPWPCS-UHFFFAOYAV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2 |
| StdInChI = 1S/C5H10O/c1-2-4-6-5-3-1/h1-5H2 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = DHXVGJBLRPWPCS-UHFFFAOYSA-N |
| StdInChIKey = DHXVGJBLRPWPCS-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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Revision as of 14:45, 29 November 2010
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| Names | |||
|---|---|---|---|
| IUPAC name
Tetrahydropyran
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| Other names
Oxacyclohexane
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| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.005.048 | ||
PubChem CID
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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, or oxane, is the organic compound consisting of a saturated six-membered ring containing five carbon atoms and one oxygen atom.
The tetrahydropyran ring system is the core of pyranose sugars.
Preparation
One classic procedure for the organic synthesis of tetrahydropyran is by hydrogenation with Raney nickel of dihydropyran.[1]
Reactions
In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols.[2][3] 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
- ^ 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.