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Chemical Structure| 37942-07-7

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Product Details of [ 37942-07-7 ]

CAS No. :37942-07-7
Formula : C15H22O2
M.W : 234.33
SMILES Code : C1=C(C(=C(C=C1C(C)(C)C)C(C)(C)C)O)C=O
MDL No. :MFCD00191998
InChI Key :RRIQVLZDOZPJTH-UHFFFAOYSA-N
Pubchem ID :688023

Safety of [ 37942-07-7 ]

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

Application In Synthesis of [ 37942-07-7 ]

* 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 [ 37942-07-7 ]

[ 37942-07-7 ] Synthesis Path-Downstream   1~25

  • 1
  • [ 37942-07-7 ]
  • [ 20439-47-8 ]
  • [ 151433-25-9 ]
YieldReaction ConditionsOperation in experiment
Heating / reflux; Chiral ligands were prepared by refluxing 1 ,2-cyclohexyldiamines {R,R and S1S) with 2,4 di-.erf-butyl salicylaldehyde
In ethanol; for 12h;Reflux; 1.14 g of (R,R)-1,2-cyclohexanediamine was dissolved in 20 mL of ethanol.4.7 g of 3,5-di-tert-butylsalicylaldehyde in 30 mL of ethanol solution was slowly added dropwise thereto.The resulting mixed solution was refluxed for 12 h.Obtaining a reaction mixture; removing the reaction solvent by filtration,The obtained reaction product ethanol was recrystallized to obtain a Schiff base ligand.The present invention performs elemental analysis on the obtained Schiff base compound,Obtaining the content of each atom therein,The results are as follows: Elem.Anal. (%): Calcd. C 79.07; H 9.95; N5.12.Found: C 78.71; H 9.85; N 4.77. this means,The Schiff base ligand obtained in this embodiment has the structure of formula II,Wherein Y is ((R,R)-1,2-cyclohexanediamine) and R is a tert-butyl group.
General procedure: In a round bottomed flask filled with argon, (1R,2R)-trans-1,2-diaminocyclohexane (R,R-DACH) (1 equiv.) and potassium carbonate (0.9 equiv.) were dissolved in 3mL of distilled water and heated for 30min at 80-85C. The exact amounts are given below. Subsequently, a solution of aldehyde (2 equiv.) in 45mL of ethanol was added dropwise and the reaction mixture was stirred for 3h. The solution turned yellow. After this time, ethanol was evaporated and 10mL of distilled water was added. Water solution was extracted with dichloromethane 3 times with 30mL of the solvent. The combined extracts were washed with brine and dried with anhydrous Na2SO4. After filtration of the drying agent, solution was evaporated to dryness. The resulting salens were subsequently reduced without purification. The resulting salens were dissolved in methanol (300mL or more if it was necessary for complete dissolution). To the salen solution, sodium borohydride (4 equiv.) was added in portions at room temperature. After addition of NaBH4, the reaction mixture was stirred for 3h and then 30mL of water was added and stirred for 15min. The alcohol was evaporated under vacuum and the water residue was extracted with DCM three times for 30mL. Organic phase was dried with Na2SO4 and after removing of the desiccant, the solvent was evaporated.
  • 2
  • [ 37942-07-7 ]
  • (R,R)-1,2-diaminocyclohexane tartrate [ No CAS ]
  • [ 135616-40-9 ]
  • 3
  • [ 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).
  • 4
  • [ 37942-07-7 ]
  • [ 4506-66-5 ]
  • N,N',N'',N'''-tetra-(3,5-di-tert-butylsalicylidene)-1,2,4,5-phenylenetetraamine [ No CAS ]
  • 6
  • [ 37942-07-7 ]
  • [ 20439-47-8 ]
  • [ 360784-94-7 ]
  • [ 135616-40-9 ]
  • C38H38N2O2 [ No CAS ]
  • [ 886055-61-4 ]
  • 7
  • [ 37942-07-7 ]
  • [ 191480-63-4 ]
  • [ 135616-40-9 ]
  • 8
  • [ 37942-07-7 ]
  • [ 4506-66-5 ]
  • (2,4-di-tert-butyl-6-({2,4,5-tri-[(3,5-di-tert-butyl-2-hydroxy-benzylidene)-amino]-phenylimino}-methyl)-phenol) [ No CAS ]
  • 9
  • [ 37942-07-7 ]
  • (R,R)-1,2-diaminocyclohexane*(+)-tartric acid [ No CAS ]
  • [ 135616-40-9 ]
  • 10
  • [ 37942-07-7 ]
  • [ 21436-03-3 ]
  • [ 135616-40-9 ]
  • 11
  • [ 14096-51-6 ]
  • [ 37942-07-7 ]
  • [ 932699-99-5 ]
  • 12
  • [ 37942-07-7 ]
  • [ 24629-25-2 ]
  • 2,4-bis(1,1-dimethylethyl)-6-([(1S,2S)-1-hydroxymethyl-2-methylbutyl]imino}methyl)phenol [ No CAS ]
  • 13
  • [ 37942-07-7 ]
  • [ 24629-25-2 ]
  • [ 1159839-76-5 ]
  • 14
  • [ 37942-07-7 ]
  • [ 7474-78-4 ]
  • [ 1217433-15-2 ]
  • 15
  • [ 50-00-0 ]
  • [ 2934-05-6 ]
  • [ 37942-07-7 ]
  • 16
  • [ 37942-07-7 ]
  • [ 5978-75-6 ]
  • [ 1223561-32-7 ]
  • 17
  • [ 37942-07-7 ]
  • (1R,2R)-1,2-diaminocyclohexane tartrate [ No CAS ]
  • [ 151433-25-9 ]
  • 18
  • [ 42726-73-8 ]
  • [ 37942-07-7 ]
  • tert-butyl 6,8-di-tert-butyl-2-oxo-2H-chromene-3-carboxylate [ No CAS ]
  • 19
  • [ 37942-07-7 ]
  • (1R,2R)-(+)-1,2-diaminocyclohexane L-tartrate [ No CAS ]
  • [ 151433-25-9 ]
  • 20
  • [ 37942-07-7 ]
  • [ 68176-57-8 ]
  • C40H56N2O2 [ No CAS ]
  • 21
  • [ 37942-07-7 ]
  • [ 68176-57-8 ]
  • C40H54N2O2Pt [ No CAS ]
  • 22
  • [ 37942-07-7 ]
  • [ 1206675-01-5 ]
  • C22H29NO2 [ No CAS ]
  • 23
  • [ 37942-07-7 ]
  • [ 4506-66-5 ]
  • 2,4-di-tert-butyl-6-((2,4,5-tri-[(3,5-di-tert-butyl-2-hydroxy-benzylidene)-amino]-phylimino)-methyl)-phenol [ No CAS ]
  • 24
  • [ 37942-07-7 ]
  • [ 36997-31-6 ]
  • C54H72N6O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% In methanol; for 24.0h;Reflux; General procedure: The ligands H6L1-7 were prepared by similar methods. A representativemethod for I is presented here. A solution of salicylaldehyde(1.46 g, 12 mmol) in MeOH (30 mL) was added to amethanolic suspension of <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>(0.504 g, 2 mmol). The reaction mixture was refluxed on an oilbath. During this period, the <strong>[36997-31-6]benzene-1,3,5-tricarbohydrazide</strong>slowly dissolved and simultaneously a white solid precipitated.After 24 h of reflux, the reaction mixture was cooled at room temperaturefor an hour, the precipitated solid was filtered, washedwith MeOH (2 5 mL) and dried in a desiccator over silica gel.Data for H6L1 (I): Yield 0.954 g (85%). Anal. Calc. for C30H24N6O6(5 6 4): C, 63.83; H, 4.29; N, 14.89. Found: C, 65.31; H, 4.82; N,13.83%. IR data (cm1): 3440 (OAH), 3018 (NAH), 1659 (CO),1563 (CN).
  • 25
  • [ 37942-07-7 ]
  • [ 41764-74-3 ]
  • N’-(3,5-di-tert-butyl-2-hydroxybenzylidene)-3,4-dimethoxybenzohydrazide [ No CAS ]
 

Historical Records

Technical Information

• Acidity of Phenols • Alkyl Halide Occurrence • Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Electrophilic Substitution of the Phenol Aromatic Ring • Etherification Reaction of Phenolic Hydroxyl Group • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Halogenation of Phenols • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nozaki-Hiyama-Kishi Reaction • Oxidation of Phenols • Passerini Reaction • Paternò-Büchi Reaction • Pechmann Coumarin Synthesis • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reformatsky Reaction • Reimer-Tiemann Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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[ 37942-07-7 ]

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