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

Description

(2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE, also known as a chiral imidazolidinone organocatalyst, is a compound developed by MacMillan and co-workers. It is characterized by its unique molecular structure, which includes a tert-butyl group at the 2nd position, a methyl group at the 3rd position, a benzyl group at the 5th position, and an imidazolidinone ring. This structure endows the compound with specific catalytic properties that are useful in various chemical reactions.

Uses

Used in the Pharmaceutical Industry:
(2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE is used as a chiral organocatalyst for the 1,4-addition of electron-rich benzenes to unsaturated aldehydes. This application is crucial in the synthesis of various pharmaceutical compounds, as it allows for the selective formation of specific stereoisomers, which can have different biological activities and properties.
Used in the Chemical Industry:
In the chemical industry, (2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE is used as a catalyst for the asymmetric hydride reduction of α,β-unsaturated aldehydes. This process is essential for the production of enantiomerically pure compounds, which are often required in the synthesis of specialty chemicals, agrochemicals, and other fine chemicals.
Overall, (2R,5R)-(+)-2-TERT-BUTYL-3-METHYL-5-BENZYL-4-IMIDAZOLIDINONE is a versatile and valuable compound in the fields of pharmaceuticals and chemical synthesis, thanks to its unique catalytic properties and ability to facilitate selective reactions.

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

Downstream Products

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

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).

Aromatic Interactions in Organocatalyst Design: Augmenting Selectivity Reversal in Iminium Ion Activation

Substituting N-methylpyrrole for N-methyindole in secondary-amine-catalysed Friedel-Crafts reactions leads to a curious erosion of enantioselectivity. In extreme cases, this substrate dependence can lead to an inversion in the sense of enantioinduction. Indeed, these closely similar transformations require two structurally distinct catalysts to obtain comparable selectivities. Herein a focussed molecular editing study is disclosed to illuminate the structural features responsible for this disparity, and thus identify lead catalyst structures to further exploit this selectivity reversal. Key to effective catalyst re-engineering was delineating the non-covalent interactions that manifest themselves in conformation. Herein we disclose preliminary validation that intermolecular aromatic (CH-π and cation-π) interactions between the incipient iminium cation and the indole ring system is key to rationalising selectivity reversal. This is absent in the N-methylpyrrole alkylation, thus forming the basis of two competing enantio-induction pathways. A simple L-valine catalyst has been developed that significantly augments this interaction.