Prolinol
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| Prolinol | |
|---|---|
  D (left) and L (right) prolinol |
|
| General | |
| Systematic name | (R or S) 2-pyrrolidinemethanol |
| Other names | |
| Molecular formula | C5H11NO |
| SMILES | ? |
| Molar mass | 101.15 g/mol |
| Appearance | Liquid |
| CAS number | [68832-13-3] (D-prolinol) [23356-96-9] (L-prolinol) |
| Properties | |
| Density and phase | 1.036 g/mL liquid |
| Solubility in water | ? g/100 ml (?°C) |
| Melting point | ?°C (? K) |
| Boiling point | 74-76 °C at 2 mmHg |
| Chiral rotation [α]D | ?° |
| Viscosity | ? cP at ?°C |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | Irritant |
| NFPA 704 | |
| Flash point | 86 °C |
| R/S statement | R: 36/37/38 S: 26-36 |
| RTECS number | ? |
| Related compounds | |
| Related compounds | ? |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.
[edit] Preparation
Prolinol is obtained by reduction of the amino acid proline using lithium aluminium hydride.[1] Because proline is cheaply available in high optical purity, enantiomerically pure prolinol is also widely available.
[edit] Use
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. [2][3]
[edit] References
- ^ 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).
- ^ 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.
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