CAS 135616-40-9 (R,R)-(-)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

Synonyms

(1R,2R)-(-)-1,2-CYCLOHEXANE DIAMINO-N,N'-BIS(3,5-DI-TERT-BUTYLSALICYLIDENE); 2,4-ditert-butyl-6-[[[(1R,2R)-2-[(3,5-ditert-butyl-6-oxocyclohexa-2,4-dien-1-ylidene)methylamino]cyclohexyl]amino]methylidene]cyclohexa-2,4-dien-1-one; ANW-54576; (1R,2R)-(-)-1,2-Cyclohexanediamino-N,N'-bis(3,5-di-t-butylsalicylidene), (R,R)-Jacobsen Ligand; MFCD00191800; 616R409; AK-58435; AC1OGTF1; (R,R)-Jacobsen inverted exclamation mark s ligand; (R,R)-1,2-bis(3,5-di-tert-butylsalicylidenamino)cyclohexane;

IUPAC Name

2,4-ditert-butyl-6-[[(1R,2R)-2-[(3,5-ditert-butyl-2-hydroxyphenyl)methylideneamino]cyclohexyl]iminomethyl]phenol;

Molecular Weight

546.84g/mol

Molecular Formula

C36H54N2O2;

Canonical SMILES

CC(C)(C)C1=CC(=C(C(=C1)C=NC2CCCCC2N=CC3=CC(=CC(=C3O)C(C)(C)C)C(C)(C)C)O)C(C)(C)C;

InChI

InChI=1S/C36H54N2O2/c1-33(2,3)25-17-23(31(39)27(19-25)35(7,8)9)21-37-29-15-13-14-16-30(29)38-22-24-18-26(34(4,5)6)20-28(32(24)40)36(10,11)12/h17-22,29-30,39-40H,13-16H2,1-12H3/t29-,30-/m1/s1;

InChI Key

FYNXDGNCEBQLGC-LOYHVIPDSA-N;

Complexity

793

Covalently-Bonded Unit Count

Defined Atom Stereocenter Count

Exact Mass

546.419g/mol

H-Bond Acceptor

H-Bond Donor

Heavy Atom Count

Monoisotopic Mass

546.419g/mol

Rotatable Bond Count

Topological Polar Surface Area

65.2A^2

Application

(R,R)-(-)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine is a yellow powder that serves as a versatile ligand, primarily used in the synthesis of Jacobsen's catalyst. Its primary purpose is to facilitate asymmetric catalysis, making it highly effective for applications such as the enantioselective epoxidation of olefins that lack functional groups. Beyond this, it supports industrial uses, including the enantioselective conjugate addition of hydrazoic acid and cyanation of unsaturated imides, as well as cobalt-catalyzed enantioselective alpha chlorination and fluorination of beta-ketoesters. As such, it plays a crucial role in processes requiring the resolution of chiral compounds and the production of biodiesel through transesterification.

March 15, 2025

Exceptional Ligand for Asymmetric Catalysis

I've been using Alfa Chemistry's (R,R)-(-)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine in my research. It serves as a versatile ligand. Perfect for preparing Jacobsen's catalyst, facilitating efficient enantioselective reactions in my laboratory.