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CAS No. : | 135616-40-9 | MDL No. : | MFCD00191800 |
Formula : | C36H54N2O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FYNXDGNCEBQLGC-LOYHVIPDSA-N |
M.W : | 546.83 | Pubchem ID : | 2733339 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | (R,R)-N,N'-Bis(5-3-tert-butyl-salicylidene)-l,2-cyclohexanediamine was synthesized following a similar procedure described by Jacobsen E. N., Zhang W., Muci A. R., Ecker J. R., and Deng L. Highly Enantioselective Epoxidation Catalysts Derived from 1,2- Diaminocyclohexane, J. Am. Chem. Soc, 113, 7063-7064 (1991). To a 250 mL round bottom flask was added 2.0053 g (8.5573 mmol) of 3,5 -tert butyl-2-hydroxybenzaldehyde that was dissolved in 20 mL absolute ethanol. Concurrently, (R5R)- 1,2-diammoniumcyclohexane mono-(+)-tartrate salt {see Larrow J. F., Jacobsen E. N., Gao Y., Hong Y., Nie X., and Zepp C. M., A Practical Process for the Large-Scale Preparation of (R,R)-N,N'-Bis(3,5-Di-tert- butylsalicylidene)-l,2-Cyclohexanediaminomanganese (III) Chloride, a Highly Enantioselective Epoxidation Catalyst, J. Org. Chem., 59, 1939-1940 (1994); (1.1219 g, 4.2451 mmol) was dissolved in a basic (NaOH) 0.2 M aqueous/absolute ethanol solution (1 :2). This salt solution was added dropwise to the benzaldehyde solution and the mixture was refluxed under nitrogen for 1 hour. The reaction mixture was filtered using a 60 mL medium frit and washed with 95% ethanol. The product was then extracted into methylene chloride. The frit was washed with additional methylene chloride until the solid was colorless. The solvent was removed under reduced pressure to yield 1.6843 gm (70%) of a yellow solid. 1H NMR: (CDCl3, ppm) delta = 1.24 (s, 9H); 1.41 (s, 9H); 1.45 (m, IH); 1.65 - 1.8 (m, IH); 1.8 - 2.0 (m, 2H); 3.32 (m, IH); 6.98 (d, IH); 7.30 (d, IH); 8.30 (s, IH); 13.72 (s, IH). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium tetrahydroborate; | (Synthesis Example of Complex 3) A salen ligand represented by the following formula (XXIX) is reduced with NaBH4 to produce a salan ligand represented by the following formula (XXX), and Ti(OiPr)4 (1.02 mmol) is added to a dichloromethane solution (2.0 mL) of the salan ligand (0.86 mmol) represented by the formula (XXX), and stirred at room temperature overnight. After few drops of water are added, the resulting mixed solution is further stirred overnight. After the solvent is distilled off under a reduced pressure, a di-mu-oxo titanium (salan) complex (complex 3) (65% yield) represented by the following formula (XXXI) is obtained through recrystallization from dichloromethane. The result of the elemental analysis of the obtained compound is C:70.21, H:9.43, N:4.31, which are well accorded with the calculated value of C72H112N4O6Ti2?0.5H2O (C:70.05, H:9.23, N:4.54). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | In ethanol; for 3h;Heating / reflux; | 5.46 g (0.01 mol) of (R,R)-2,2'-[1,2-cyclohexanediyl)bis(nitrilomethylidyne)]-bis[4,6-di-tert-butyl)phenol] are initially charged in 50 ml of ethanol and admixed with 1.14 g (0.0045 mmol) of vanadyl sulfate pentahydrate. After three hours under reflux and complete conversion (TLC monitoring), the solvent is distilled off, the residue taken up in 200 ml of dichloromethane and the solution washed with 100 ml of water. After phase separation, drying of the solution with sodium sulfate and distilling off the solvent, 5.4 g of bright green, amorphous powder (yield: 96% of theory) are obtained. [0049] Characterization: [TABLE-US-00001] Color bright green Melting point 208 C., with decomposition[alpha]D20 = -300 (c = 0.01; CHCl3) paramagnetic IR (KBr) nu = 2950 (s), 2870 (m), 2350 (w), 2320 (w), 1610 (vs), 1550 (m), 1270 (s) [cm-1]. |
A263243[ 135616-36-3 ]
(S,S)-(+)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine
Reason: Optical isomers