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Chemical Structure| 135616-40-9

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Product Details of [ 135616-40-9 ]

CAS No. :135616-40-9
Formula : C36H54N2O2
M.W : 546.83
SMILES Code : OC1=C(C(C)(C)C)C=C(C(C)(C)C)C=C1/C=N/[C@H]2[C@H](/N=C/C3=CC(C(C)(C)C)=CC(C(C)(C)C)=C3O)CCCC2
MDL No. :MFCD00191800
InChI Key :FYNXDGNCEBQLGC-LOYHVIPDSA-N
Pubchem ID :2733339

Safety of [ 135616-40-9 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 135616-40-9 ]

* 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.

  • Downstream synthetic route of [ 135616-40-9 ]

[ 135616-40-9 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 37942-07-7 ]
  • (R,R)-1,2-diaminocyclohexane tartrate [ No CAS ]
  • [ 135616-40-9 ]
  • 2
  • [ 37942-07-7 ]
  • (1R,2R)-1,2-diaminocyclohexane tartrate [ No CAS ]
  • [ 135616-40-9 ]
YieldReaction ConditionsOperation 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).
  • 3
  • [ 616-02-4 ]
  • [ 135616-40-9 ]
  • [ 147396-58-5 ]
  • [ 357418-52-1 ]
  • 4
  • [ 80-62-6 ]
  • [ 135616-40-9 ]
  • [ 147396-58-5 ]
  • methyl (R)-(-)-4-methylcyclohex-3-ene-4-carboxylate [ No CAS ]
  • 5
  • [ 135616-40-9 ]
  • [ 147396-58-5 ]
  • [ 624-49-7 ]
  • [ 137492-80-9 ]
  • 7
  • [ 37942-07-7 ]
  • [ 20439-47-8 ]
  • [ 360784-94-7 ]
  • [ 135616-40-9 ]
  • C38H38N2O2 [ No CAS ]
  • [ 886055-61-4 ]
  • 8
  • [ 135616-40-9 ]
  • (1,2-dimethoxyethane-O,O')calcium bis[bis(trimethylsilyl)amide] [ No CAS ]
  • (1,2-dimethoxyethane-O,O')calcium(R,R)-(-)-N,N'-bis[3,5-di(tert-butyl)salicylate]-1,2-cyclohexenediimine [ No CAS ]
  • 9
  • [ 135616-40-9 ]
  • [ 812693-91-7 ]
YieldReaction ConditionsOperation 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).
  • 10
  • [ 37942-07-7 ]
  • [ 191480-63-4 ]
  • [ 135616-40-9 ]
  • 11
  • [ 37942-07-7 ]
  • (R,R)-1,2-diaminocyclohexane*(+)-tartric acid [ No CAS ]
  • [ 135616-40-9 ]
  • 13
  • [ 694-83-7 ]
  • [ 135616-40-9 ]
  • 14
  • chromium dichloride [ No CAS ]
  • [ 135616-40-9 ]
  • (R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediaminochromium(III) chloride [ No CAS ]
  • 15
  • [ 37942-07-7 ]
  • [ 21436-03-3 ]
  • [ 135616-40-9 ]
  • 16
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 135616-40-9 ]
  • 2C36H54N2O2*OV [ No CAS ]
YieldReaction ConditionsOperation 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].
  • 17
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 135616-40-9 ]
  • C36H54N2O2*OV [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In ethanol; for 3h;Heating / reflux; 5.56 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 2.53 g (0.01 mol) 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, 7.7 g of dark green, amorphous powder (yield: 81% of theory) are obtained. [0053] Characterization (cf. Y. N. Belokon: Tetrahedron 57, 2001, 777): [TABLE-US-00002] Color dark green Melting point 233 C.[alpha]D20 = 1000 (c = 0.01; CHCl3) diamagnetic IR (KBr) nu = 2950 (s), 2870 (m), 2350 (w), 2320 (w), 1610 (vs), 1550 (m), 1250 (vs), 1210 (s), 1010 (m) [cm-1].
  • 18
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 135616-40-9 ]
  • C36H54N2O2*O2V2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In ethanol; for 2h;Heating / reflux; 8.0 g (0.015 mol) of (R,R)-2,2'-[1,2-cyclohexanediyl)bis(nitrilomethylidyne)]-bis[4,6-di-tert-butyl)phenol] are initially charged in 200 ml of ethanol and admixed with 2.5 g (0.01 mol) of vanadyl sulfate pentahydrate. After two 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, 8.2 g of green, amorphous powder (yield: 87% of theory, based on a complex having vanadium:salen ligand=1:2).
  • 19
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 135616-40-9 ]
  • [VO(C6H10(NCHC6H2(C(CH3)3)2O)2)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% In ethanol; for 3h;Heating / reflux; 5.56 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 2.53 g (0.01 mol) 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, 5.7 g of dark green, amorphous powder (yield: 81% of theory, based on a vanadium:salen ligand of 1:1) are obtained.
  • 20
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 135616-40-9 ]
  • 22C36H54N2O2*10OV(2+)*10O4S(2-) [ No CAS ]
YieldReaction ConditionsOperation 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 mol) 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, based on a vanadium:salen ligand ratio of 1:2) are obtained.
  • 21
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 135616-40-9 ]
  • C360H540N20O95S15V15 [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol; for 3h;Heating / reflux; 5.56 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 3.8 g (0.015 mol) 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, 5.0 g of green, amorphous powder are obtained.
YieldReaction ConditionsOperation in experiment
In dichloromethane; for 21h;Heating / reflux;Reactivity (does not react); 5,46 g (0,01 mol) (R, R)-2, 2 - [1, 2-CYCLOHEXANDIYL) bis (nitrilomethylidyn)] bis [4,6-di- TERT.-BUTYL)-PHENOL] (Illa) werden in 50 ml Dichlormethan vorgelegt und mit 1,26 g (0,005 mol) VANADYLSULFAT-PENTAHYDRAT in 50 ml Dichlormethan versetzt. Nach 21 Stunden unter Rueckfluss wird das Loesungsmittel abdestilliert, und der Rueckstand per HPLC untersucht. Zusammensetzung des Gemischs nach HPLC (Gew. -%) : Komponente (I) : (11) : (LUI) =0% : 0% 100%.
  • 23
  • oxovanadium(IV) sulfate [ No CAS ]
  • [ 135616-40-9 ]
  • (O)V(S,S)-N,N'-bis-(3,5-di-tert-butylsalicylidene)-1,2-cyclohexenediamine-2H) [ No CAS ]
YieldReaction ConditionsOperation in experiment
In methanol; dichloromethane; at 20 - 40℃; for 1 - 24h; Beispiel 1 244,3 g (0.448 moi) (R, R)-2, 2 - [1, 2-CYCLOHEXANDIYL) bis (nitrilomethylidyn)] bis [4,6-di- tert.-butyl)-phenol] (Illa) werden in 1500 ML Dichlormethan geloest und mit einer Loesung von 60,0 g (0,237 mol) Vanadylsulfat-Pentahydrat in 2000 ml Methanol versetzt. Die Reaktionsmischung ruehrt fuer 24 h bei Raumtemperatur. Anschliessend wird das Loesungsmittel abdestilliert, der Rueckstand in 1000 ml Dichlormethan aufgenommen und mit 1000 ml Wasser gewaschen. Nach Phasentrennung, Trocknen der organischen Loesung mit Natriumsulfat und Abdestillieren des Loesungsmittels erhaelt man 247,7 g gruenes, amorphes Pulver. Zusammensetzung des Gemischs nach HPLC (Gew. -%) : Komponente (I) : (II) : (III) =68% : 13% : 19%. [A] D20 =-400 (c = 0,01, Chloroform). Beispiel 2 5,46 g (0.01 mol) (R, R)-2, 2 - [1, 2-CYCLOHEXANDIYL) bis (nitrilomethylidyn)] bis [4,6-di- tert.-butyl)-phenol] (Illa) werden in 12,5 ml Dichlormethan geloest und mit einer Loesung von 1,26 g (0,005 mol) VANADYLSULFAT-PENTAHYDRAT in 12,5 ML Methanol versetzt. Die Reaktionsmischung ruehrt fuer eine Stunde bei 40 C. Anschliessend wird das Loesungsmittel abdestilliert, der Rueckstand in 50 ml Dichlormethan aufgenommen und mit 100 ml Wasser gewaschen. Nach Phasentrennung, Trocknen der organischen Loesung mit Natriumsulfat und Abdestillieren des Loesungsmittels erhaelt man 3,5 g gruenes, amorphes Pulver. Zusammensetzung des Gemischs nach HPLC (Gew. -%) : Komponente (I) : (H) : (III) = 71 % : 10% : 19%.
In tetrahydrofuran; ethanol; for 3h;Heating / reflux; 5,46 G (0,01 mol) (R, R)-2, 2'- [1, 2-Cyclohexandiyl) bis (nitrilomethylidyn)] bis [4,6-di- tert.-butyl)-phenol] (Illa) werden in 25 ml THF vorgelegt und mit 1,26 g (0,005 mol) VANADYLSULFAT-PENTAHYDRAT in 25 ml Ethanol versetzt. Nach drei Stunden unter Rueckfluss wird das Loesungsmittel abdestilliert, der Rueckstand in 50 mi Dichlormethan aufgenommen und die Loesung mit 300 ml Wasser gewaschen. Nach Phasentrennung, Trocknen der Loesung mit Natriumsulfat und Abdestillieren des Loesungsmittels erhaelt man 3,6 g gruenes, amorphes Pulver. Zusammensetzung des Gemischs nach HPLC (Gew. -%) : Komponente (I) : (II) : (III) =43% : 13% : 44 %.
In ethanol; for 2h;Heating / reflux; Beispiel 3 5,46 g (0,01 mol) (R, R)-2, 2'- [1, 2-Cyclohexandiyl) bis (nitrilomethylidyn)] bis [4,6-di- tert.-butyl)-phenol] (ILLA) werden in 50 mi Ethanol vorgelegt und mit 1,14 g (0,0045 mol) Vanadylsulfat-Pentahydrat versetzt. Nach zwei Stunden unter Rueckfluss wird das Loesungsmittel abdestilliert, der Rueckstand in 200 ml Dichlormethan aufgenommen und die Loesung mit 100 mi Wasser gewaschen. Nach Phasentrennung, Trocknen der Loesung mit Natriumsulfat und Abdestillieren des Loesungsmittels erhaelt man 4,8 g gruenes, amorphes Pulver. Zusammensetzung des Gemischs nach HPLC (Gew. -%) : Komponente (I) : (LL) : (III) =61 % : 12% : 27%. [A] O =-350 (c = 0,01, Chloroform). Beispiel 4 5,46 g (0,01 mol) (R, R)-2, 2 - [1, 2-CYCLOHEXANDIYL) bis (nitrilomethylidyn)] bis [4,6-di- tert.-butyl)-phenol] (Illa) werden in 50 ml Ethanol vorgelegt und mit 0,86 g (0,0034 mol) Vanadylsulfat-Pentahydrat versetzt. Nach zwei Stunden unter Rueckfluss wird das Loesungsmittel abdestilliert, der Rueckstand in 200 ml Dichlormethan aufgenommen und die Loesung mit 100 ml Wasser gewaschen. Nach Phasentrennung, Trocknen der Loesung mit Natriumsulfat und Abdestillieren des Loesungsmittels erhaelt man 3,8 g gruenes, amorphes Pulver. Zusammensetzung des Gemischs nach HPLC (Gew. -%) : Komponente (I) : (LL) : (III) = 44 % : 8% : 48%. [alpha]D20 = -350 (c = 0,01, Chloroform).
  • 24
  • [ 67-56-1 ]
  • [ 71-48-7 ]
  • [ 64-19-7 ]
  • [ 135616-40-9 ]
  • C39H59CoN2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
(R,R)-Jacobsen's ligand 1 (82 g, 0.15 mol, 1.0 equiv) was charged to a 3-L, 3-neck round bottom flask equipped w/mechanical stirrer, thermometer, and air-sparging dip tube. MeOH (750 mL) was then charged to the vessel at ambient temperature. Glacial Acetic Acid (18 g, 0.3 mol, 2.0 equiv) was then charged to the flask. Co(OAc)2.4H2O (41.9 g, 0.165 mol, 1.1 equiv) was charged to the reaction vessel and an additional 75 mL MeOH (approx. 10 volumes total) was used as a rinse. The contents of the flask were stirred open to the air for 30 minutes until most of the ligand solids had dissolved. Then, an air stream was pulled through the dark green/brown mixture via house vacuum using a dip tube open to the atmosphere with stirring for 2 hours. The contents of the flask were monitored for consumption of ligand and absence of Co(II)salen catalyst by TLC. When monitoring indicated completion of the reaction, the sparge tube was replaced with an addition funnel and water (850 mL) was slowly added over 2-3 hours (slowly at first, portionwise) via the addition funnel to precipitate the active Co(III) ligand catalyst complex 2. Brown solids were isolated by vacuum filtration of the contents of the reaction vessel through Whatman 3 paper on a Buchner funnel. The solids were washed with water (2×350 mL) and air dried. The solids were scraped off of the filter paper and dried in a vacuum oven at 35 C. under house vacuum to yield 105 g (quantitative) of a dark brown solid, identified by NMR analysis as Co(III) ligand catalyst complex 2. The NMR spectrum was consistent with the expected complex containing a molecule of methanol coordinated to cobalt, thereby filling the metal's sixth coordination site.
  • 25
  • [ 373-02-4 ]
  • [ 135616-40-9 ]
  • Ni((R,R)-N,N-bis(3,5-di-tert-butylsalicylidene)cyclohexane-1,2-diamine) [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In methanol; dichloromethane; water; at 3 - 20℃; for 2.5h; Ni(salen*) was prepared as follows: First, to a 250 mL round bottom flask was added 1.0087 g (1.8446 mmol) of (R,R)-N,N'-Bis(5-3-tert-butyl-salicylidene)-l,2- cyclohexanediamine that was dissolved in 44 mL of methylene chloride. Concurrently, Ni?(OAc)24H2O (0.5076 g, 2.040 mmol) was dissolved in 25 mL of dry methanol. The nickel solution was added dropwise to the reaction mixture was stirred for 2 hours at room temperature. The mixture was then cooled to 3 C in an ice bath and stirred for an additional 0.5 hour. The solid product was filtered using a 60 mL medium frit and washed with cold dry methanol until the filtrate became clear. The solid was dried under vacuum overnight. The yield of the complex was 0.7316 g (66%). 1H NMR: (CDCl3, ppm) mu = 1.28 (s, 9H); 1.34 (m, EPO <DP n="13"/>2H); 1.43 (s, 9H); 1.92 (m, IH); 2.45 (m, IH); 2.99 (m, IH); 6.90 (d, J = 2.4Hz, IH); 7.31 (d, IH); 7.40 (s, IH). ELEMENTAL ANALYSIS: Theoretical (%) C 71.41, H 8.99, N 4.63, Ni 9.69. Experimental (%) C 71.72, H 8.66, N 4.57, Ni 9.55.
  • 26
  • [ 6147-53-1 ]
  • [ 135616-40-9 ]
  • [ 176763-62-5 ]
  • 27
  • [ 638-38-0 ]
  • [ 135616-40-9 ]
  • lithium chloride [ No CAS ]
  • chloro(N,N'-bis(3,5-di-tert-butysalicylidenate)-1,2-diaminocyclohexane)manganese(III) [ No CAS ]
  • 28
  • [ 6156-78-1 ]
  • [ 135616-40-9 ]
  • [ 7647-14-5 ]
  • [ 138124-32-0 ]
  • 29
  • trans-1,2-cyclohexanediamine [ No CAS ]
  • [ 135616-40-9 ]
 

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[ 135616-40-9 ]

Chemical Structure| 135616-36-3

A263243 [135616-36-3]

(S,S)-(+)-N,N'-Bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamine

Reason: Optical isomers