415678-40-9

Basic information

• Product Name: (2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95%
• Synonyms: (2s,5s)-5-benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidone;(2S,5S)-5-Benzyl-3-Methyl-2-(5-Methylfuran-2-yl)iMidazolidin-4-one;(2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone 95%
• CAS NO: 415678-40-9
• Molecular Formula: C16H18N2O2
• Molecular Weight: 270.33
• Mol File: 415678-40-9.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 438.6 °C at 760 mmHg
• Flash Point: >110℃
• Appearance: /
• Density: 1.155 g/cm³
• Vapor Pressure: 6.84E-08mmHg at 25°C
• Refractive Index: n20/D1.5598
• PKA: 4.44±0.60(Predicted)
• CAS DataBase Reference: (2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95%(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95%(415678-40-9)
• EPA Substance Registry System: (2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95%(415678-40-9)

Safety Data

• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-36-45
• RIDADR: UN 2810 6.1 / PGIII
• WGK Germany: 3
• Hazardous Substances Data: 415678-40-9(Hazardous Substances Data)

Usage

Description

(2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95% is a chiral imidazolidinone derivative with a unique structure featuring a benzyl group and a furyl group. It is a high purity compound, which makes it suitable for various applications in the fields of chemistry and pharmaceuticals.

Uses

Used in Enantioselective Organocatalytic Transfer Hydrogenation:
(2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95% is used as a catalyst for enantioselective organocatalytic transfer hydrogenation of cycloalkenones with tert-Bu Hantzsch ester as the source of hydrogen. This application is significant for the synthesis of chiral compounds with high enantiomeric purity, which are essential in the pharmaceutical industry.
Used in Alkylation of Indoles:
In the pharmaceutical industry, (2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95% is used as a catalyst in the alkylation of indoles with an α,β-disubstituted α,β-unsaturated aldehyde. This process is crucial for the enantioselective preparation of a selective serotonin reuptake inhibitor, which is an important class of antidepressant drugs.
Used in MacMillan Reaction:
(2S,5S)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95% is also utilized in the MacMillan reaction, a widely used method in organic chemistry for the synthesis of complex molecules. This application highlights the versatility of the compound in facilitating various chemical transformations, contributing to the development of new pharmaceuticals and other specialty chemicals.

InChI:InChI=1/C16H18N2O2/c1-11-8-9-14(20-11)15-17-13(16(19)18(15)2)10-12-6-4-3-5-7-12/h3-9,13,15,17H,10H2,1-2H3/t13-,15-/m0/s1

Upstream product

• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 620-02-0 5-Methylfurfural 
• 35373-92-3 L-phenylalanine methylamide 

Relevant articles and documents

Basicities and Nucleophilicities of Pyrrolidines and Imidazolidinones Used as Organocatalysts

The Br?nsted basicities pKaH (i.e., pKa of the conjugate acids) of 32 pyrrolidines and imidazolidinones, commonly used in organocatalytic reactions, have been determined photometrically in acetonitrile solution using CH acids as indicators. Most investigated pyrrolidines have basicities in the range 16 aH aH aH 12.6) and the 2-imidazoliummethyl-substituted pyrrolidine A21 (pKaH 11.1) are outside the typical range for pyrrolidines with basicities comparable to those of imidazolidinones. Kinetics of the reactions of these 32 organocatalysts with benzhydrylium ions (Ar2CH+) and structurally related quinone methides, common reference electrophiles for quantifying nucleophilic reactivities, have been measured photometrically. Most reactions followed second-order kinetics, first order in amine and first order in electrophile. More complex kinetics were observed for the reactions of imidazolidinones and several pyrrolidines carrying bulky 2-substituents, due to reversibility of the initial attack of the amines at the electrophiles followed by rate-determining deprotonation of the intermediate ammonium ions. In the presence of 2,4,6-collidine or 2,6-di-tert-butyl-4-methyl-pyridine, the deprotonation of the initial adducts became faster, which allowed the rate of the attack of the amines at the electrophiles to be determined. The resulting second-order rate constants k2 followed the correlation log?k2(20 °C) = sN(N + E), where electrophiles are characterized by one parameter (E) and nucleophiles are characterized by the two solvent-dependent parameters N and sN. In this way, the organocatalysts A1-A32 were integrated in our comprehensive nucleophilicity scale, which compares n-, -, and σ-nucleophiles. The nucleophilic reactivities of the title compounds correlate only poorly with their Br?nsted basicities.

Enantioselective transformation of alpha,beta-unsaturated ketones using chiral organic catalysts

Nonmetallic organic catalysts are provided that facilitate the enantioselective reaction of α,β-unsaturated ketones. The catalysts are chiral imidazolidinone compounds having the structure of formula (IIA) or (IIB) or are acid addition salts thereof, wherein, in one preferred embodiment, R1 is C1-C6 alkyl, R2is phenyl or 2-methylfuryl, R3 and R4 are hydrogen, and R5 is phenyl optionally substituted with 1 or 2 substituents selected from the group consisting of halo, hydroxyl, and C1-C6 alkyl The chiral imidazolidinones are useful in catalyzing a wide variety of reactions, including cycloaddition reactions, Friedel-Crafts alkylation reactions, and Michael additions.