1-[(8R,9R)-12-acetyl-4,13-dimethyl-8,9-bis(2,4,6-trimethylphenyl)-1,3-dioxa-7,10-diaza-2-cobaltacyclotrideca-4,6,10,12-tetraen-5-yl]ethan-1-one

• ChemBase ID: 143034
• Molecular Formular: C32H38CoN2O4
• Molecular Mass: 573.58832
• Monoisotopic Mass: 573.21635271
• SMILES: Cc1cc(c(c(c1)C)[C@@H]1/N=C\C(=C(/O[Co]O/C(=C(\C=N\[C@@H]1c1c(cc(cc1C)C)C)/C(=O)C)/C)\C)\C(=O)C)C
• Canonical SMILES: Cc1cc(C)c(c(c1)C)[C@@H]1/N=C\C(=C(\C)/O[Co]O/C(=C(\C=N\[C@@H]1c1c(C)cc(cc1C)C)/C(=O)C)/C)\C(=O)C
• InChI: InChI=1S/C32H40N2O4.Co/c1-17-11-19(3)29(20(4)12-17)31(33-15-27(23(7)35)24(8)36)32(34-16-28(25(9)37)26(10)38)30-21(5)13-18(2)14-22(30)6;/h11-16,31-32,35,37H,1-10H3;/q;+2/p-2/t31-,32-;/m1./s1
• InChIKey: PHCQQLMRNZRDJA-JOVGIXRXSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(8R,9R)-12-acetyl-4,13-dimethyl-8,9-bis(2,4,6-trimethylphenyl)-1,3-dioxa-7,10-diaza-2-cobaltacyclotrideca-4,6,10,12-tetraen-5-yl]ethan-1-one
• IUPAC Traditional name: 1-[(8R,9R)-12-acetyl-4,13-dimethyl-8,9-bis(2,4,6-trimethylphenyl)-1,3-dioxa-7,10-diaza-2-cobaltacyclotrideca-4,6,10,12-tetraen-5-yl]ethanone
• Synonyms: (R,R)-AMAC; (1R,2R)-N,N′-Bis(2-acetyl-3-oxo-2-butenylidene)-1,2-dimesitylethylenediaminato cobalt(II); (1R,2R)-N,N′-双(2-乙酰-3-氧代-2-亚丁烯基)-1,2-二均三甲苯基乙二胺合钴(II)

Database IDs

• CAS Number: 361346-80-7
• MDL Number: MFCD06797061
• PubChem SID: 162237258
• PubChem CID: 11226930

CALCULATED PROPERTIES

• Acid pKa: 18.646933
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 5.644822
• LogD (pH = 7.4): 5.654673
• Log P: 5.6548
• Molar Refractivity: 155.899 cm^3
• Polarizability: 61.11089 Å^3
• Polar Surface Area: 77.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 246-250 °C
• Optical Rotation: [α]/D 291°, c = 0.1 in chloroform

Product Information

• Purity: ≥97%
• Empirical Formula (Hill Notation): C32H38CoN2O4

DETAILS

Sigma Aldrich - 708550

Application
Catalyst used for the enantioselective reduction of ketones, hetero Diels-Alder reaction, carbonylene reaction, 1,3-dipolar cycloaddition9

• Schiff base-cobalt complex catalyst for asymmetric borohydride reduction of carbonyl compounds1Catalyst for:
• Enantioselective borohydride reduction2
• Stereoselective preparation of aryl alcohols via asymmetric reduction of aryl ketones with borohydride3
• Stereoselective borohydride reduction of diketones to diols4
• Stereoselective preparation of optically active deuterated primary alcohols via enantioselective borodeuteride reduction of aldehydes5
• Stereoselective preparation of β-hydroxy esters via dynamic kinetic resolution of alkylketo esters with enantioselective borohydride reduction6
• Chemoselective, diastereoselective, and enantioselective borohydride reduction of 1,3-diketones7
• Asymmetric synthesis of diarylhydroxypropanones by stereoselective reduction of alkyldiaryldiketones8
Packaging
100, 500 mg in glass bottle