2,4-di-tert-butyl-6-{N-[(1R,2R)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carboximidoyl}phenol

• ChemBase ID: 147709
• Molecular Formular: C36H54N2O2
• Molecular Mass: 546.82616
• Monoisotopic Mass: 546.41852898
• SMILES: CC(c1cc(c(c(c1)/C=N/[C@H]1[C@@H](CCCC1)/N=C/c1c(c(cc(c1)C(C)(C)C)C(C)(C)C)O)O)C(C)(C)C)(C)C
• Canonical SMILES: Oc1c(/C=N/[C@@H]2CCCC[C@H]2/N=C/c2cc(cc(c2O)C(C)(C)C)C(C)(C)C)cc(cc1C(C)(C)C)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
• InChIKey: FYNXDGNCEBQLGC-LOYHVIPDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,4-di-tert-butyl-6-{N-[(1R,2R)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carboximidoyl}phenol
• IUPAC Traditional name: 2,4-di-tert-butyl-6-{N-[(1R,2R)-2-{[(3,5-di-tert-butyl-2-hydroxyphenyl)methylidene]amino}cyclohexyl]carboximidoyl}phenol
• Synonyms: (R,R)-Jacobsen’s ligand; (R,R)-(-)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine; (R,R)-Jacobsen 配体; (R,R)-(-)-N,N′-双(3,5-二-叔丁基亚水杨基)-1,2-环己二胺

Database IDs

• CAS Number: 135616-40-9
• MDL Number: MFCD00191800
• Beilstein Number: 5464823
• PubChem SID: 24865244; 162241894
• PubChem CID: 5702535

CALCULATED PROPERTIES

• Acid pKa: 9.452425
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 9.923665
• LogD (pH = 7.4): 10.634766
• Log P: 10.66021
• Molar Refractivity: 171.9314 cm^3
• Polarizability: 65.7757 Å^3
• Polar Surface Area: 65.18 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Melting Point: 205-207 °C(lit.)
• Optical Rotation: [α]20/D -315±15°, c = 1 in methylene chloride

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 98%
• Linear Formula: [[(CH3)3C]2C6H2-2-(OH)CH=N]2C6H10

DETAILS

Sigma Aldrich - 404411

Biochem/physiol Actions
Lipases catalyze the hydrolysis of triacylglycerols into glycerol and free fatty acids.
α-amylase catalyzes the hydrolysis of internal α-1,4-O-glycosidic bonds in starches to release α-anomeric sugars.2
Packaging
1, 5 g in glass bottle
Legal Information
Manufactured under license by Shasun Chemicals and Drugs Limited, using Jacobsen HKR technology.
Application
Amylases from Aspergillus oryzae are used to prevent staling in the baking industry, clarify haze from fruit juices and alcoholic beverages, and produce glucose and maltose syrup products.1
Versatile ligand for asymmetric catalysis. Ligand used for preparing Jacobsen′s catalyst suitable for enantioselective epoxidation of olefins lacking functional groups.Lipases are used industrially for the resolution of chiral compounds and the transesterification production of biodiesel.