390766-89-9

Basic information

• Product Name: (2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE
• Synonyms: (2R,5R)-2-T-BUTYL-3-METHYL-5-PHENYLMETHYL-4-IMIDAZOLIDINONE;(2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE;(2R,5R)-2-TERT-BUTYL-3-METHYL-5-PHENYLMETHYL-4-IMIDAZOLIDINONE;MACMILLAN ORGANOCATALYST(TM) RR246;(2R,5R)-2-TERT-BUTYL-3-METHYL-5-BENZYL-&;(2R,5R)-(+)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone,(2R,5R)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone;(2R,5R)-(+)-2-tert-Butyl-3-Methyl-5-benzyl-4-iMidazolidinone 97%;(2R,5R)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one
• CAS NO: 390766-89-9
• Molecular Formula: C15H22N2O
• Molecular Weight: 246.35
• Mol File: 390766-89-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 93-100°C
• Boiling Point: 378°C at 760 mmHg
• Flash Point: 182.4°C
• Appearance: /
• Density: 1.04g/cm³
• Vapor Pressure: 6.47E-06mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 5.59±0.60(Predicted)
• CAS DataBase Reference: (2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE(390766-89-9)
• EPA Substance Registry System: (2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE(390766-89-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 390766-89-9(Hazardous Substances Data)

Usage

Uses

Used in the 1,4-addition of electron-rich benzenes to unsaturated aldehydes, and the asymmetric hydride reduction of α,β-unsaturated aldehydes.

General Description

(2R,5R)-(+)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a chiral imidazolidinone organocatalyst, developed by MacMillan and co-workers.

InChI:InChI=1/C15H22N2O/c1-15(2,3)14-16-12(13(18)17(14)4)10-11-8-6-5-7-9-11/h5-9,12,14,16H,10H2,1-4H3/t12-,14-/m1/s1

Upstream product

• 35373-92-3 L-phenylalanine methylamide 
• 630-19-3 pivalaldehyde 
• 1608182-03-1 C₂₀H₃₀N₂O 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 63-91-2 L-phenylalanine 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 691847-46-8 (2R,5S)-5-benzyl-2-tert-butyl-3-methylimidazolin-4-one hydrochloride 
• 346440-54-8 (2S,5S)-5-benzyl-2-(tert-butyl)-3-methylimidazolidin-4-one 

Downstream Products

• 1608182-03-1 C₂₀H₃₀N₂O 
• 1646630-39-8 (2S,5S)-5-benzyl-2-(tert-butyl)-3-methyl-4-oxoimidazolidin-1-ium Tetrafluoroborate 
• 1646629-44-8 (2R,5S)-5-benzyl-2-(tert-butyl)-3-methyl-4-oxoimidazolidin-1-ium tetrafluoroborate 
• 188290-36-0 thiophene 

Relevant articles and documents

Asymmetric hydroalkylation of alkynes and allenes with imidazolidinone derivatives: α-alkenylation of α-amino acids

This work reports a new method for the synthesis of quaternary α-alkenyl substituted amino acids by the enantio- and diastereoselective addition of imidazolidinone derivatives to alkynes and allenes. Further hydrolysis of the imidazolidinone products under acidic conditions afforded biologically relevant amino acid derivatives. This method is geometry-selective (E-isomer), enantio- and diastereoselective, and products were obtained in good to excellent yields. The utility of this new methodology is proved by its operational simplicity and the successful accomplishment of gram-scale reactions. Experimental and computational studies suggest the key role of Li in terms of selectivity and support the proposed reaction mechanism.

UNNATURAL AMINO ACIDS

The present invention relates to a process for the preparation compounds of Formula (I): Formula (I) wherein X, Z, Q, Ar, R1, R2, R3 and R4 are each as defined herein. The present invention also relates to processes for the preparation of the compounds of quaternary amino acids and hydantions, to compound of Formula(I), to intermediate compounds of Formula (II), to quaternary amino acid compounds of Formula (III) and to hydantoin compounds of Formula (IV).

Enantioselective oxidation of thioanisole to metyl phenyl sulfoxide by chiral compounds bearing N-Cl bond

Chiral sulfoxides are used in asymmetric synthesis and are present in various biologically active compounds. Asymmetric synthesis of the sulfoxides has been performed by chiral metal complexes and non-metals containing peroxide and oxide moieties. In this study, a new metal free method has been developed to oxidize thioanisole into methyl phenyl sulfoxide with easily accessible chiral compounds carrying N-Cl bond. For this purpose, chiral amine and amide bearing reagents were synthesized and chlorinated by using N-chlorosuccinimide. In oxidation reactions, chiral information has been transferred from N-chloramines to sulfides. With chlorinated chiral reagents, we observed enantioenriched sulfoxide formation. Although the observed results are promising, the best chiral amines are yet to be found. This is the first report on such a reaction, to the best of our knowledge.