336105-87-4

Basic information

• Product Name: (R,R)-N,N'-bis(3-methyl-salicylidene)-1,2-cyclohexanediamine
• Synonyms: (R,R)-N,N'-bis(3-methyl-salicylidene)-1,2-cyclohexanediamine
• CAS NO: 336105-87-4
• Molecular Weight: 350.461
• Mol File: 336105-87-4.mol

Chemical Properties

• CAS DataBase Reference: (R,R)-N,N'-bis(3-methyl-salicylidene)-1,2-cyclohexanediamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-N,N'-bis(3-methyl-salicylidene)-1,2-cyclohexanediamine(336105-87-4)
• EPA Substance Registry System: (R,R)-N,N'-bis(3-methyl-salicylidene)-1,2-cyclohexanediamine(336105-87-4)

Safety Data

• Hazardous Substances Data: 336105-87-4(Hazardous Substances Data)

Upstream product

• 824-42-0 2-methoxy-3-methylbenzaldehyde 
• 32044-22-7 (R,R)-1,2-diaminocyclohexane*(+)-tartric acid 
• 32044-22-7 (R,R)-1,2-diaminocyclohexane tartrate 

Relevant articles and documents

A practical approach to the resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction with a lipophilic chiral salen-cobalt(III) complex

(Chemical Equation Presented) Liquidating the assets: Coordination of one enantiomer from a racemic mixture of N-benzyl α-amino acids (N-Bn-AA) to the lipophilic chiral [CoIII(salen)(OAc)] complex results in its extraction into the organic phas

Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction: A practical method using a lipophilic chiral cobalt(III) salen complex and mechanistic studies

The efficient resolution of racemic N-benzyl α-amino acids (N-Bn-AA) has been achieved by a liquid-liquid extraction process using the lipophilic chiral salen-cobalt(III) complex [CoIII(3)(OAc)]. As a result of the resolution by extraction, one enantiomer (S) of the N-benzyl α-amino acid predominated in the aqueous phase, while the other enantiomer (R) was driven into the organic phase by complexation to cobalt. The complexed amino acid (R) was then quantitatively released by a reductive (CoIII→Co II) counter-extraction with aqueous sodium dithionite or L-ascorbic acid in methanol. The reductive cleavage allowed to recover the [Co II(3)] complex in good yield, which could be easily re-oxidized to [CoIII(3)(OAc)] with air/AcOH and reused with essentially no loss of reactivity and selectivity. Investigation on the nitrogen substitution indicates that the presence of a single benzyl group on the amino acid nitrogen is important to obtain high enantioselectivity in the extraction process. The kinetic vs. thermodynamic nature of the resolution process was also investigated with an enantiomeric exchange experiment, which shows that the liquid-liquid extraction with [CoIII(3)-(OAc)] is an equilibrium process operating under thermodynamic control. In the absence of a suitable crystal structure of the [CoIII(3)(N-Bn-AA)] complexes, computational and spectroscopic studies were used to investigate how the N-benzyl α-amino acids are accommodated in the "binding pocket" of the chiral cobalt complex. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Diastereomerically-specific zirconium complexes of chiral salan ligands: Isospecific polymerization of 1-hexene and 4-methyl-1-pentene and cyclopolymerization of 1,5-hexadiene

Chiral Salan ligands were found to wrap in a highly diastereoselective manner around zirconium leading to C2-symmetric complexes of predetermined chirality at the metal. These complexes led to active polymerization of higher olefins, their activity and is