Substance
ID:714084
Names and Identifiers
IUPAC Traditional name
L-proline
IUPAC name
(2S)-pyrrolidine-2-carboxylic acid
Synonyms
L-脯氨酸(S)-Pyrrolidine-2-carboxylic acidL-ProlineH-Pro-OH
Registration numbers
Beilstein Number
CAS Number
EC Number
MDL Number
Merck Index
Properties
Physical Property
Optical Rotation
-84 (c=1 in water)
Melting Point
ca 225°C dec.
Density
1.36
Safety Information
RTECS
TW3584000
Storage Warning
Hygroscopic
TSCA Listed
是
Product Information
Purity
99%
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
• For preparation from L-proline of the chiral hydrazone "SAMP", and enantioselective syntheses using the RAMP/ SAMP methodology, see: Org. Synth. Coll., 8, 26, 403 (1985).
• For formation of a fused pyrrolidino-oxazolidinone, and use of the product in a synthesis of enantiopure ɑ-branched amino acids, see: Org. Synth. Coll., 9, 626 (1998); for reaction scheme, see Trimethylacetaldehyde, A15013.
• For use as a catalyst in an asymmetric aldol cyclization, see: Org. Synth. Coll., 7, 363 (1990). For reaction scheme, see 2-Methylcyclopentane-1,3-dione, A13936. For use in a direct enantioselective crossed aldol reaction with aldehydes, see: J. Am. Chem. Soc., 124, 6798 (2002). For use as an organoctalyst in direct aldol reactions of ɑ-oxyaldehydes, as the first step in a two-step synthesis of carbohydrates, see: Angew. Chem. Int. Ed., 43, 2152 (2004). Mediates the enantioselective borane reduction of ketones to chiral alcohols with moderate to good ee: Monatsh. Chem., 131, 91 (2000). Also used to induce high ee in the ɑ-amination of aldehydes with Dibenzyl azodicarboxylate, L19347: J. Am. Chem. Soc., 124, 5656 (2002), or Diethyl azodicarboxylate, L19348: Angew. Chem. Int. Ed., 41, 1790 (2002).
• The Li salt has been used as a catalyst for the Michael addition of dimethyl malonate to ɑ?-unsaturated aldehydes: J. Chem. Soc., Chem. Commun., 1088 (1991).
• For a review of the use of proline as a chiral catalyst, see: Synlett, 1675 (2001); Synlett, 1973 (2006).