(2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone

Base Information

• Chemical Name: (2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone
• CAS No.: 415678-40-9
• Molecular Formula: C₁₆H₁₈N₂O₂
• Molecular Weight: 270.331
• European Community (EC) Number: 623-815-9
• Nikkaji Number: J1.709.132H
• Wikidata: Q76416937
• Mol file: 415678-40-9.mol

Synonyms:415678-40-9;(2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone;(2S,5S)-5-benzyl-3-methyl-2-(5-methylfuran-2-yl)imidazolidin-4-one;4-Imidazolidinone,3-methyl-2-(5-methyl-2-furanyl)-5-(phenylmethyl)-, (2S,5S)-;SCHEMBL2150474;(2S,5S)-5-BENZYL-3-METHYL-2-(5-METHYL-2-FURYL)-4-IMIDAZOLIDINONE;IQIMPHPFMHVWBZ-ZFWWWQNUSA-N;MFCD08457653;BS-52972;C80093;(2S, 5S)-5-Benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one;(2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone, 95%

Chemical Property of (2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone

Chemical Property:

• Vapor Pressure: 6.84E-08mmHg at 25°C
• Refractive Index: 1.566
• Boiling Point: 438.6 °C at 760 mmHg
• PKA: 4.44±0.60(Predicted)
• Flash Point: 219 °C
• PSA: 45.48000
• Density: 1.155 g/cm³
• LogP: 2.52620
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 270.136827821
• Heavy Atom Count: 20
• Complexity: 354

Purity/Quality:

98%,99%, ^*data from raw suppliers

(2S,5S)-(–)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-36-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC=C(O1)C2NC(C(=O)N2C)CC3=CC=CC=C3
• Isomeric SMILES: CC1=CC=C(O1)[C@H]2N[C@H](C(=O)N2C)CC3=CC=CC=C3
• Uses: Catalyst for:Enantioselective organocatalytic transfer hydrogenation of cycloalkenones with tert-Bu Hantzsch ester as source of hydrogenAlkylation of indoles with an α,β-disubstituted α,β-unsaturated aldehyde in the enantioselective preparation of a selective serotonin reuptake inhibitorMacMillan reaction

Technology Process of (2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone

There total 6 articles about (2S,5S)-(-)-5-Benzyl-3-methyl-2-(5-methyl-2-furyl)-4-imidazolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.0%

5-Methylfurfural (620-02-0) + L-phenylalanine methylamide (35373-92-3) → (2R,5S)-5-benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one (415678-40-9,415678-56-7) + (2S,5S)-5-benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one (415678-40-9,415678-56-7)

Guidance literature:

With 4 A molecular sieve; samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; at 25 ℃; for 29h;

DOI:10.1021/ja017641u

Reference yield: 46.0%

5-Methylfurfural (620-02-0) + L-phenylalanine methylamide (35373-92-3) → (2R,5S)-5-benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one (415678-40-9,415678-56-7) + (2S,5S)-5-benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one (415678-40-9,415678-56-7)

Guidance literature:

With 4 A molecular sieve; samarium(III) trifluoromethanesulfonate; In tetrahydrofuran; at 25 ℃; for 29h;

DOI:10.1021/ja017641u

Reference yield:

(L)-phenylalanine ethyl ester hydrochloride (3182-93-2) → (2R,5S)-5-benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one (415678-40-9,415678-56-7) + (2S,5S)-5-benzyl-3-methyl-2-(5-methyl-furan-2-yl)-imidazolidin-4-one (415678-40-9,415678-56-7)

Guidance literature:

Multi-step reaction with 2 steps

1: methylamine / ethanol / 95 h

2: ytterbium(III) triflate / chloroform / 8 h / Reflux

With methylamine; ytterbium(III) triflate; In ethanol; chloroform;

DOI:10.1016/j.tet.2011.04.009

upstream raw materials:

5-Methylfurfural

L-phenylalanine methylamide

(L)-phenylalanine ethyl ester hydrochloride

Refernces

• 1、 Samulis, Leopold,Tomkinson, Nicholas C.O.. "Preparation of the MacMillan imidazolidinones". supporting information; experimental part. p. 4263 - 4267. Retrieved 2011/06/26.
• 2、 Northrup, Alan B.,MacMillan, David W. C.. "The first general enantioselective catalytic Diels-Alder reaction with simple (α,β-unsaturated ketones". . p. 2458 - 2460. Retrieved 2007/10/03.