(4S,9S)-14,16,22,24-tetra-tert-butyl-19-chloro-18,20-dioxa-3,10-diaza-19-manganatetracyclo[19.4.0.04,9.012,17]pentacosa-1(21),2,10,12,14,16,22,24-octaene

• ChemBase ID: 127927
• Molecular Formular: C36H52ClMnN2O2
• Molecular Mass: 635.201329
• Monoisotopic Mass: 634.30977669
• SMILES: CC(C)(C)c1cc2/C=N\[C@H]3CCCC[C@@H]3/N=C\c3cc(cc(c3O[Mn](Cl)Oc2c(c1)C(C)(C)C)C(C)(C)C)C(C)(C)C
• Canonical SMILES: Cl[Mn]1Oc2c(/C=N\[C@@H]3[C@@H](/N=C\c4c(O1)c(cc(c4)C(C)(C)C)C(C)(C)C)CCCC3)cc(cc2C(C)(C)C)C(C)(C)C
• InChI: InChI=1S/C36H54N2O2.ClH.Mn/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;1H;/q;;+3/p-3/t29-,30-;;/m0../s1
• InChIKey: LJVAWOSDJSQANR-ARDORAJISA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,9S)-14,16,22,24-tetra-tert-butyl-19-chloro-18,20-dioxa-3,10-diaza-19-manganatetracyclo[19.4.0.0^4,^9.0^1^2,^1^7]pentacosa-1(21),2,10,12,14,16,22,24-octaene
• IUPAC Traditional name: (4S,9S)-14,16,22,24-tetra-tert-butyl-19-chloro-18,20-dioxa-3,10-diaza-19-manganatetracyclo[19.4.0.0^4,^9.0^1^2,^1^7]pentacosa-1(21),2,10,12,14,16,22,24-octaene
• Synonyms: (S,S)-Jacobsen’s catalyst; (S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride; Jacobsen's catalyst; (S,S)-(+)-N,N′-双(3,5-二-叔丁基亚水杨基)-1,2-环己二胺氯化锰(III); (S,S)-Jacobsen 催化剂

Database IDs

• CAS Number: 135620-04-1; 149656-63-3
• MDL Number: MFCD02101663
• PubChem SID: 24865247
• Chemspider ID: 21171274
• Wikipedia Title: Jacobsen's_catalyst

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 10.985141
• LogD (pH = 7.4): 11.40012
• Log P: 11.4087
• Molar Refractivity: 175.6389 cm^3
• Polarizability: 70.25387 Å^3
• Polar Surface Area: 43.18 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: brown solid
• Melting Point: 330-332 °C; 330-332 °C(lit.)

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• 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: ≥96.0% (CHN)
• Grade: purum
• Linear Formula: [[[(CH3)3C]2C6H2-2-(O-)CH=N]2C6H10]MnCl

DETAILS

Sigma Aldrich - 404454

Application
Salen (Mn)-catalyzed asymmetric epoxidation of unfunctionalized olefins.6,7,8,9 High enantioselectivities and yields are obtained for a variety of substrates,6 especially cis-alkenes. A few applications include the synthesis of the taxol side chain10 and cis-1-amino-2-indanol.11,12 Jacobsen′s catalyst has also been used in the asymmetric α-hydroxylation of silyl enol ethers.13 Catalyst for the enantioselective epoxidation of a variety of olefins.13,14
Reactant involved in:
• Studies of intercalative binding with ct-DNA and radical scavenging antioxidant activity1
• Immobilization on phenoxy-modified zirconium poly(styrenephenylvinylphosphonate)2
• Synthesis of derivatvies for studies of conformational models of enantioselective reactions3Catalyst involved in:
• Asymmetric epoxidation of olefins4
• Immobilization on ionic liquid modified mesoporous silica for oxidative kinetic resolution of racemic secondary alcohols†
• Immobilization on diamine modified zirconium olig-styrenyl phosphonate hydrogen phosphate for epoxidation of styrene5
Packaging
1, 5, 25 g in glass bottle
Legal Information
Manufactured under license by Shasun Chemicals and Drugs Limited, using Jacobsen HKR technology.

Sigma Aldrich - 14717

Application
Reactant involved in:
• Studies of intercalative binding with ct-DNA and radical scavenging antioxidant activity1
• Immobilization on phenoxy-modified zirconium poly(styrenephenylvinylphosphonate)2
• Synthesis of derivatvies for studies of conformational models of enantioselective reactions3Catalyst involved in:
• Asymmetric epoxidation of olefins4
• Immobilization on ionic liquid modified mesoporous silica for oxidative kinetic resolution of racemic secondary alcohols†
• Immobilization on diamine modified zirconium olig-styrenyl phosphonate hydrogen phosphate for epoxidation of styrene5