(2 S ) - (-) - exo - (dimethylamino) isoborneol
Structural formula | |||||||||||||
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General | |||||||||||||
Surname | (2 S ) - (-) - exo - (dimethylamino) isoborneol | ||||||||||||
other names |
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Molecular formula | C 12 H 23 NO | ||||||||||||
Brief description |
colorless oil |
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properties | |||||||||||||
Molar mass | 198.18 g mol −1 | ||||||||||||
Physical state |
firmly |
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boiling point |
150 ° C |
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solubility |
good in ethanol , toluene and dichloromethane |
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safety instructions | |||||||||||||
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
(2 S ) - (-) - exo - (dimethylamino) isoborneol , mostly abbreviated as DAIB , is an organic chemical compound that can be structurally derived from isoborneol . The chiral compound is sometimes used as an enantioselective catalyst .
Extraction and presentation
The starting product for the synthesis of (2 S ) - (-) - exo - (dimethylamino) isoborneol is (1 R , 4 S ) - (-) - camphorquinone monoxime. From this, (2 S ) - (-) - 3- exo- aminoisoborneol is produced by reduction with lithium aluminum hydride . To introduce the still missing methyl groups, a carbamate is first produced with triphosgene and then the first methyl group is introduced with methyl iodide . In order to obtain the final product, the carbamate is finally reduced with lithium aluminum hydride.
Properties and use
DAIB is a colorless liquid that dissolves well in most organic solvents such as ethanol , toluene and dichloromethane . The compound acts as an enantioselective catalyst in the reduction of aldehydes with organic zinc compounds . The reaction of benzaldehyde with diethylzinc under DAIB catalysis produces ( S ) -1-phenyl-1-propanol with an enantiomeric excess of 95.4% ee and 97% yield. The compound thus enables a high enantiomeric excess in the product, although the catalyst has a significantly lower enantiomeric purity.
DAIB decomposes slowly in air and must therefore be stored under inert gases such as nitrogen or argon .
Individual evidence
- ↑ a b c d James D. White, Duncan J. Wardrop, and Kurt F. Sundermann: (2S) - (-) - exo- (dimethylamino) isoborneol [(2S) - (-) - DAIB] In: Organic Syntheses . 79, 2002, p. 130, doi : 10.15227 / orgsyn.079.0130 ( PDF ).
- ↑ a b Grant R. Krow, Kevin C. Cannon: Encyclopedia of Reagents for Organic Synthesis: (1R, 2S, 3R, 4S) -3-Dimethylamino-1,7,7-trimethylbicyclo [2.2.1] heptane-2- oil. October 15, 2003.
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ Masato Kitamura, Hiromasa Oka, Seiji Suga, Ryoji Noyori : Catalytic enantioselective addidion of dialkylzincs to aldehydes using (2S) - (-) - exo- (dimethylamino) isoborneol [(2S) -DAIB]: (S) -1-phenyl -1-propanol In: Organic Syntheses . 79, 2002, p. 139, doi : 10.15227 / orgsyn.079.0139 ( PDF ).