(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone - ≥97%(GC) , CAS No.346440-54-8

CAS: 346440-54-8 Cat. No.: S161185 Molecular Weight: 246.35 PubChem CID: 10309834

GRADE & PURITY ≥97%(GC)

Synonyms

Q27270710 | (2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone | T70804 | (2S,5S)-(-)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone | J-019688 | AKOS000272101 | NSC 400336 | Macmillan's imidazolidinone catalysts second generation catalyst [MI

Storage

Room temperature

Shipped In

Normal

Overview

product description：

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

application：

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a second-generation MacMillan catalyst, which can be used as a chiral organocatalyst in:

The chiral transformation reaction, including Friedel-Crafts and Mukaiyama-Michael reactions.

The preparation of substituted spiroundecenetriones via asymmetric domino Knoevenagel/Diels-Alder reactions.

The asymmetric synthesis of β-hydroxy aldehydes and their dimethylacetals via aldehyde-aldehyde aldol condensation reaction.

The enantioselective α-fluorination of aldehydes using N-fluorobenzenesulfonamide as a fluorinating agent.

The stereoselective preparation of (oxomethyl)oxabicyclo[3.2.1]octenones and tricyclic pyrroles via [4+3] cycloaddition of (trialkylsiloxy)pentadienals to furans.

Metal-free OrganoCatalyst technology for asymmetric catalysis. Catalyzes asymmetric indole alkylations, Friedel-Crafts alkylations, and a broad range of conjugate addition reactions in high enantiomeric excess.

Specifications

Synonyms

Q27270710 | (2S, 5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone | T70804 | (2S, 5S)-(-)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone | J-019688 | AKOS000272101 | NSC 400336 | Macmillan's imidazolidinone catalysts second generation catalyst [MI

Specifications & Purity

≥97%(GC)

Storage

Room temperature

Shipped In

Normal

Purity

≥97%(GC)

Names and Identifiers

• Canonical Smiles: CC(C)(C)C1NC(C(=O)N1C)CC2=CC=CC=C2
• IUPAC Name: (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one
• InChIKey: SKHPYKHVYFTIOI-JSGCOSHPSA-N
• INCHI: 1S/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-/m0/s1
• Isomeric SMILES: CC(C)(C)[C@H]1N[C@H](C(=O)N1C)CC2=CC=CC=C2
• WGK Germany: 3
• PubChem CID: 10309834
• Molecular Weight: 246.35
• Reaxy-Rn: 6480916

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives
• Direct Parent: Alpha amino acids and derivatives
• Alternative Parents: Imidazolidinones Benzene and substituted derivatives Tertiary carboxylic acid amides Lactams Azacyclic compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds Amines
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha-amino acid or derivatives - Monocyclic benzene moiety - Benzenoid - Imidazolidinone - Imidazolidine - Tertiary carboxylic acid amide - Carboxamide group - Lactam - Azacycle - Organoheterocyclic compound - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Hydrocarbon derivative - Organic oxide - Carbonyl group - Organic oxygen compound - Amine - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Specific Rotation[α]: -60° (C=1,MeOH)
• Melt Point(°C): 100 °C
• Molecular Weight: 246.350 g/mol
• XLogP3: 3.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 246.173 Da
• Monoisotopic Mass: 246.173 Da
• Topological Polar Surface Area: 32.299 Ų
• Heavy Atom Count: 18
• Formal Charge: 0
• Complexity: 302.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1