Prolinol
From Wikipedia, the free encyclopedia
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| Names | |||
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| IUPAC name
(R or S) 2-pyrrolidinemethanol
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| Identifiers | |||
68832-13-3 (D-prolinol)  23356-96-9 (L-prolinol)  |
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| ChemSpider | 2006673 (D-prolinol) 555468 (L-prolinol) |
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| Jmol 3D model | (D-prolinol): Interactive image (L-prolinol): Interactive image |
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| PubChem | 2724541 (D-prolinol) 640091 (L-prolinol) |
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| Properties | |||
| C5H11NO | |||
| Molar mass | 101.15 g/mol | ||
| Appearance | Liquid | ||
| Density | 1.036 g/mL liquid | ||
| Boiling point | 74 to 76 °C (165 to 169 °F; 347 to 349 K) at 2 mmHg | ||
| Hazards | |||
| Main hazards | Irritant | ||
| R-phrases | 36/37/38 | ||
| S-phrases | 26-36 | ||
| Flash point | 86 °C (187 °F; 359 K) | ||
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |||
- This article is about a compound used in synthesis of certain stimulants and should not be confused with a stimulant in that class the brand name of which is propalin
Prolinol is a chiral amino-alcohol that is used as a chiral building block in organic synthesis. It exists as two enantiomers: the D and L forms.
Contents
Preparation[edit]
Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.[1][2] Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.
Use[edit]
Prolinol is used in broad variety of chemical reactions as chiral ligand, chiral catalyst or chiral auxiliary reagent in the Hajos-Parrish-Eder-Sauer-Wiechert reaction, the Baylis-Hillman reaction, Noyori type reaction and the Michael reaction. [3][4]
See also[edit]
References[edit]
- ^ Dickman, D. A.; Meyers, A. I.; Smith, G. A.; Gawley, R. E. Reduction of α-Amino Acids: L-Valinol Organic Syntheses, Collected Volume 7, p.530 (1990).
- ^ Enders D.; Fey P.; Kipphardt, H. [1] Organic Syntheses, Collected Volume 8, p.26 (1993).
- ^ Benjamin List (2002). "Proline-catalyzed asymmetric reactions". Tetrahedron. 58 (28): 5573–5590. doi:10.1016/S0040-4020(02)00516-1.
- ^ Shinichi Itsuno, Koichi Ito, Akira Hirao and Seiichi Nakahama (1984). "Asymmetric synthesis using chirally modified borohydrides. Part 2. Enantioselective reduction of ketones with polymeric (S)-prolinol–borane reagent". J. Chem. Soc., Perkin Trans. 1 (12): 2887–2895. doi:10.1039/P19840002887.
