L511188

(S)-2-(2,3-Bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride

Aldrich^CPR

• Synonyme(s) : (βS)-β-[[2,3-bis(dicyclohexylamino)-2-cyclopropen-1-ylidene]amino]-benzenepropanol hydrochloride (1:1), Dicyclohexyl cyclopropenimine, Lambert Cyclopropenimine Catalyst
• Formule empirique (notation de Hill): C₃₆H₅₆ClN₃O
• Numéro CAS: 1366421-67-1
• Poids moléculaire : 582.30
• Numéro MDL: MFCD22417240
• Code UNSPSC : 12352200
• ID de substance PubChem : 329817511

Propriétés

• Chaîne SMILES: Cl.OC[C@H](Cc1ccccc1)\N=C2\C(N(C3CCCCC3)C4CCCCC4)=C2N(C5CCCCC5)C6CCCCC6
• InChI: 1S/C36H55N3O.ClH/c40-27-29(26-28-16-6-1-7-17-28)37-34-35(38(30-18-8-2-9-19-30)31-20-10-3-11-21-31)36(34)39(32-22-12-4-13-23-32)33-24-14-5-15-25-33;/h1,6-7,16-17,29-33,40H,2-5,8-15,18-27H2;1H/t29-;/m0./s1
• Clé InChI: RTCSAEOYHXMTHG-JMAPEOGHSA-N

Description

Description générale

Learn More at the Professor and Product Portal of Professor Tristan Lambert.

Application

Chiral cyclopropenimines are highly effective new class of enantioselective Brønsted base catalysts, the so-called “superbases” for enantioselective organocatalysis.

Due to the prevalence of chemical reactions involving proton transfer as a key mechanistic event, Brønsted bases have become indispensable tools for the practice of organic synthetic chemistry, capable of catalyzing proton transfer reactions enantioselectively for the production of optically enriched products.

Novel Brønsted bases provide potent yet tunable basicity to the acidity of a given substrate, are trivial to prepare, and offer unique opportunities for asymmetric transition state organization. The high basicity should allow them to catalyze a wide range of reactions (i.e. chiral pharmaceutical ingredients) and could lead to easier and faster syntheses of novel chiral compounds for drug discovery and other applications.

2,3-bis(dialkylamino)cyclopropenimines serve as a highly effective platform for chiral Brønsted base catalysis. Chiral 2,3-bis(dialkylamino)cyclopropenimine catalyzes the rapid Michael reaction of a glycine imine substrate with high levels of enantioselectivity. Catalysis with chiral cyclopropenimines should be amenable to relatively large-scale applications under mild reaction conditions.

Autres remarques

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Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable