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(2S,5S)-(−)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone

97%

Sinônimo(s):

(2S,5S)-2-tert-Butyl-3-methyl-5-phenylmethyl-4-imidazolidinone, (2S,5S)-5-Benzyl-2-tert-butyl-3-methyl-4-imidazolidinone

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About This Item

Fórmula empírica (Notação de Hill):
C15H22N2O
Número CAS:
Peso molecular:
246.35
Número MDL:
Código UNSPSC:
12352005
ID de substância PubChem:
NACRES:
NA.22
Preço e disponibilidade não estão disponíveis no momento.

Nível de qualidade

Ensaio

97%

Formulário

solid

pf

93-100 °C (lit.)

grupo funcional

phenyl

cadeia de caracteres SMILES

CN1[C@H](N[C@@H](Cc2ccccc2)C1=O)C(C)(C)C

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

chave InChI

SKHPYKHVYFTIOI-JSGCOSHPSA-N

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Descrição geral

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a chiral imidazolidinone organocatalyst, developed by MacMillan and co-workers.[1]

Aplicação

(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.[2]
  • The preparation of substituted spiroundecenetriones via asymmetric domino Knoevenagel/Diels-Alder reactions.[3]
  • The asymmetric synthesis of β-hydroxy aldehydes and their dimethylacetals via aldehyde-aldehyde aldol condensation reaction.[4]
  • The enantioselective α-fluorination of aldehydes using N-fluorobenzenesulfonamide as a fluorinating agent.[5]
  • The stereoselective preparation of (oxomethyl)oxabicyclo[3.2.1]octenones and tricyclic pyrroles via [4+3] cycloaddition of (trialkylsiloxy)pentadienals to furans.[6]

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.

Características e benefícios

Advantages of MacMillan imidazolidinone organocatalysts:[1]
  • Superior enantiocontrol in numerous transformations
  • High activities at low catalyst loadings
  • Extraordinary functional group tolerance

Informações legais

U.S. Pat. 6,369,243 and related patents apply. For research purposes only.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)


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Visite a Biblioteca de Documentos

The Importance of Iminium Geometry Control in Enamine Catalysis: Identification of a New Catalyst Architecture for Aldehyde-Aldehyde Couplings
Mangion IK, et al.
Angewandte Chemie (International Edition in English), 116(48), 6890-6892 (2004)
Teresa D Beeson et al.
Science (New York, N.Y.), 316(5824), 582-585 (2007-03-31)
The asymmetric alpha-addition of relatively nonpolar hydrocarbon substrates, such as allyl and aryl groups, to aldehydes and ketones remains a largely unsolved problem in organic synthesis, despite the wide potential utility of direct routes to such products. We reasoned that
Evaluation of protonation sites in two MacMillan catalysts in solution by gas phase predissociation spectroscopy and electronic structure calculations
Tavares LC, et al.
Organic Chemistry, 134-145 (2020)
Asymmetric organocatalysis of 4+ 3 cycloaddition reactions
Harmata M, et al.
Journal of the American Chemical Society, 125(8), 2058-2059 (2003)
Organocatalytic Asymmetric Domino Knoevenagel/Diels-Alder Reactions: A Bioorganic Approach to the Diastereospecific and Enantioselective Construction of Highly Substituted Spiro [5, 5] undecane-1, 5, 9-triones
Ramachary DB, et al.
Angewandte Chemie (International Edition in English), 42(35), 4233-4237 (2003)

Artigos

Discover Professor David MacMillan's groundbreaking metal-free asymmetric catalysis using imidazolidinone-based organocatalysts for versatile transformations.

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