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Merck
CN

404454

(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride

Synonym(s):

(S,S)-Jacobsen’s catalyst

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About This Item

Linear Formula:
[[[(CH3)3C]2C6H2-2-(O-)CH=N]2C6H10]MnCl
CAS Number:
135620-04-1
Molecular Weight:
635.20
NACRES:
NA.22
PubChem Substance ID:
24865247
UNSPSC Code:
12352101
MDL number:
MFCD02101663

Key Documents

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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/b37-21+,38-22+;;/t29-,30-;;/m0../s1

SMILES string

CC(C)(C)c1cc2C=[N@@H]3[C@H]4CCCC[C@@H]4[N@H]5=Cc6cc(cc(c6O[Mn]35(Cl)Oc2c(c1)C(C)(C)C)C(C)(C)C)C(C)(C)C

InChI key

LJVAWOSDJSQANR-RUIQGICGSA-K

mp

330-332 °C (lit.)

Quality Level

200

Related Categories

General description

(S,S)-(+)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminomanganese(III) chloride is a metal-salen complex that can catalyze a variety of asymmetric transformations.

Application

Reactant involved in:
  • Studies of intercalative binding with ct-DNA and radical scavenging antioxidant activity
  • Immobilization on phenoxy-modified zirconium poly(styrenephenylvinylphosphonate)
  • Synthesis of derivatvies for studies of conformational models of enantioselective reactions

Catalyst involved in:
  • Asymmetric epoxidation of olefins
  • 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 styrene
Salen (Mn)-catalyzed asymmetric epoxidation of unfunctionalized olefins. High enantioselectivities and yields are obtained for a variety of substrates, especially cis-alkenes. A few applications include the synthesis of the taxol side chain and cis-1-amino-2-indanol. Jacobsen′s catalyst has also been used in the asymmetric α-hydroxylation of silyl enol ethers. Catalyst for the enantioselective epoxidation of a variety of olefins.

Legal Information

Manufactured under license by Sterling Pharma Solutions Limited, using Jacobsen HKR technology.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCQ2811
MKBX7136V
MKBN0606V
13405EJ
08121AJ

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Zhang, W. Jacobsen, E.N.
The Journal of Organic Chemistry, 56, 2296-2296 (1991)
Senanayake, C.H. et al.
Tetrahedron Letters, 36, 3993-3993 (1995)
Adam, W. et al.
Tetrahedron, 37, 6531-6531 (1996)
Lee, N.H. et al.
Tetrahedron Letters, 32, 5055-5055 (1991)
Senanayake, C.H. et al.
Tetrahedron Letters, 37, 3271-3271 (1996)
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