Key Documents

404411

(R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

Name: (R,R)-(−)-N,N′-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
Brand: ALDRICH

98%

Synonym(s):

(R,R)-Jacobsen’s ligand

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About This Item

Linear Formula:

[[(CH₃)₃C]₂C₆H₂-2-(OH)CH=N]₂C₆H₁₀

CAS Number:

135616-40-9

Molecular Weight:

546.83

UNSPSC Code:

12352116

NACRES:

NA.22

PubChem Substance ID:

24865244

MDL number:

MFCD00191800

Beilstein/REAXYS Number:

5464823

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Properties

Quality Level

100

assay

98%

form

solid

optical activity

[α]20/D −315±15°, c = 1 in methylene chloride

mp

205-207 °C (lit.)

functional group

imine

SMILES string

CC(C)(C)c1cc(\C=N\[C@@H]2CCCC[C@H]2\N=C\c3cc(cc(c3O)C(C)(C)C)C(C)(C)C)c(O)c(c1)C(C)(C)C

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/b37-21+,38-22+/t29-,30-/m1/s1

InChI key

FYNXDGNCEBQLGC-LQWPWIHBSA-N

Description

Application

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.

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.

Biochem/physiol Actions

α-amylase catalyzes the hydrolysis of internal α-1,4-O-glycosidic bonds in starches to release α-anomeric sugars.

Lipases catalyze the hydrolysis of triacylglycerols into glycerol and free fatty acids.

Legal Information

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

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

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

Regulatory Information

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Articles

Salen Ligands

The first reports of salen used as ligands with manganese for asymmetric epoxidation reactions.

Salen配体

Salen配体：Jacobsen和Katsuki在1990年分别发表了第一篇关于salen作为锰的配体用于不对称环氧化反应的报道。

S. Chang et al.

The Journal of Organic Chemistry, 58, 6939-6939 (1993)

Journal of the American Chemical Society, 113, 7063-7063 (1991)

L. Deng et al.

The Journal of Organic Chemistry, 57, 4320-4320 (1992)

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Global Trade Item Number

SKU	GTIN
404411-1G	04061831986839
404411-5G	04061832623054