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CAS No. : | 13482-22-9 | MDL No. : | MFCD02093817 |
Formula : | C6H10O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | BXBJZYXQHHPVGO-UHFFFAOYSA-N |
M.W : | 114.14 | Pubchem ID : | 543706 |
Synonyms : |
|
Num. heavy atoms : | 8 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.83 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 30.2 |
TPSA : | 37.3 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.15 cm/s |
Log Po/w (iLOGP) : | 1.19 |
Log Po/w (XLOGP3) : | -0.22 |
Log Po/w (WLOGP) : | 0.49 |
Log Po/w (MLOGP) : | 0.07 |
Log Po/w (SILICOS-IT) : | 1.22 |
Consensus Log Po/w : | 0.55 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -0.41 |
Solubility : | 44.5 mg/ml ; 0.39 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.11 |
Solubility : | 89.4 mg/ml ; 0.783 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.57 |
Solubility : | 30.5 mg/ml ; 0.267 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.37 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H227-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 |
---|---|---|
91% | at 0 - 20℃; for 12.5 h; Inert atmosphere | General procedure: 4-Hydroxy-cyclohexanone 1 (2.0 mmol) was dissolved in 3 mL of pyridine at 0 °C. The corresponding acid chloride 2 (1.5 equiv) was added drop-wise at this temperature over a period of 30 min. After stirring for 12 h at room temperature, the mixture was directly poured on a column of silica gel and purified by flash chromatography (hexane/ethyl acetate 1:1). The esters 3-16 were isolated as colorless oils in analytically pure form in the yields given in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With acetic acid; In ethanol; at 20℃; for 3h;Heating / reflux; | EXAMPLE 4; 2,3,4,9-Tetrahvdro-l-flr-carbazol-3-oI FCompound No. 41:; To a solution of <strong>[13482-22-9]4-hydroxycyclohexanone</strong> (0.970 g, 8.220 mmol) in acetic acid(10 mL) phenylhydrazine (1.216 g, 11.249 mmol) was added dropwise, with stirring, at room temperature. The material began to crystallise almost immediately and additional acetic acid (5 mL) and ethanol (5 mL) were added. The reaction mixture was then heated under reflux for 3 hours. The resulting dark red solution was concentrated under reduced pressure to about 6 mL and then diluted with a sufficient amount of water to produce clouding. Cooling and scratching induced crystallisation. The mixture was filtered and the solid was washed with water. Crystallisation from methanol/water followed by recrystallisation from ethyl acetate/n-hexane gave the required product as a tan solid (670 mg, 44%), mrhol48-150C [Gardner, P. D.; Haynes, G.R. and Brandon, R.L., J.Org.Chem., 1957, 22, 1206-1210, mpl48.5-149.5C], RF=0.32 (ethyl acetate/n- hexane 1/1). IR(KBr): 3384, 2920, 2843, 1620, 1453, 1367, 1324, 1054, 1004, 744, 637 cm."1 H1 NMR (CDCl3): 7.81 (IH5 br); 7.52(1H, d, J=7.4Hz); 7.34(1H, d, J=7.4Hz); 7.19(1H, t, J=6.3Hz); 7.16(1H, t, 6.3Hz); 4.33(1H, m); 3.18(1H, dd, J=4.8Hz & J=15.2Hz); 2.98-2.74(3H, m); 2.22-2.04(2H, m); 1.77(1H, br). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium bromate; ammonium cerium (IV) nitrate; In water; acetonitrile; for 2.5h;Reflux; | Cerium (IV) ammonium nitrate (45.4 g, 82.85 mmol) and sodium bromate (125 g, 0.828 mol) were added to a solution of 1 ,4-cyclohexanediol (commercially available from Sigma-Aldrich, Milwaukee, WI, 278 g, 2.393 mol) in ACN (2.7 L) and water (1.15 L). The resulting mixture was heated at reflux for 2.5 hours and then cooled to room temperature. The resulting solution was extracted with chloroform (1 L x 3), and the combined organic extracts were dried, filtered and concentrated to afford 4-hydroxycyclohexanone (245 g, 91%). m/z (ESI) 1 15 (M+H)+. |
75% | With Jones reagent; In acetone; at 0 - 20℃; for 0.666667h;Inert atmosphere; | In a three-necked round-bottom flask fitted with a mechanical stir, cyclohexane-1,4-diol (5.8 g, 50 mmol) was dissolved in 200 mL of acetone. The solution was cooled to 0 C, and freshly prepared Jones reagent (1.6 M in acetone) was added over 25 min. The green-blue solution was allowed to warm to room temperature over 15 min. The reaction mixture was filtered over celite and the solvent was removed in vacuo. Flash column chromatography (hexane/ethyl acetate 1:2) gave 4-hydroxy-cyclohexanone 1 (4.28 g, 75%) as a colorless oil.Rf=0.64 (hexane/ethyl acetate 1:3); 1H NMR (300 MHz, CDCl3) delta=1.18-2.01 (m, 4H, 6-H, 2-H), 2.20-2.30 (m, 2H, 3-H), 2.50-2.57 (m, 2H, 5-H), 2.59 (s, 1H, OH), 4.10-4.15 (m, 1H, 1-H); 13C NMR (300 MHz, CDCl3) delta=33.5, 37.1 (2t, C-2,6, C-3,5), 65.9 (d, C-1), 211.6 (s, C-4) in accordance to literature. |
With sodium bromate; ammonium cerium(IV) nitrate; In water; acetonitrile; for 1.5h;Heating / reflux; | A 100 g 1,4-hexanediol was dissolved in 1.4 L of a mixture of acetonitrile and water (7:3 by volume). A mixture of 45.4 g of sodium bromate and 16.5 g of ammonium cerium (IV) nitrate was slowly added. The reaction was maintained under reflux conditions for 90 min. Once acetonitrile was removed by rotary evaporation, the solution was diluted with 800 mL of water and continuously extracted with chloroform for 72 h. The organic solution was dried over magnesium sulfate. Finally chloroform was evaporated from the organic solution to yield 99.5 g of a colorless oil (4-hydroxycyclohexanone). 130 g of benzyl chloride were slowly added to a solution of 60 g of 4-hydroxycyclohexanone in 400 mL of triethylamine. The solution was left to react at 25 C. for 2 h. After removal of the solvent, the product was purified by column chromatography to yield 100 g of a white powder 4-benzylestercyclohexanone. To a solution of 20 g 3-chloroperoxybenzoic acid in 200 mL of chloroform was added a solution of 15 g of 4-benzylestercylohexanone in 100 mL of chloroform. The reaction proceeded at 25 C. for 14 h. The solution was passed through Celite, extracted with brine and water successively. The solution was dried over magnesium sulfate and the solvent evaporated. Finally, the product was re-crystallized from a solution of ethyl acetate:hexane (1:4) to yield 7 g of white powder, benzylester protected 4-hydroxylcaprolactone (p-CLOH). 50 mg of 1,6-hexandiol, 20 g of D,L lactide (DLL) monomer and 4 g of p-CLOH were dried by azeotropic distillation of toluene. The monomers were heated to 140 C. to add stannous octoate (0.5 mol %) under a blanket of argon. The reaction was left to proceed at 160 C. for 14 h. The resulting polymer poly(DLL-pCLOH) was dissolved in acetone, precipitated in methanol and dried under reduced pressure. The benzyl protecting group was removed by dissolving 10 g of poly(DLL-pCLOH) in 100 ml of anhydrous ethyl acetate and adding 0.8 g of tin(IV) chloride under a blanket of argon. The reaction proceeded at 25 C. for 90 min. The resulting polymer poly(DLL-CLOH) was precipitated in methanol and dried under reduced pressure. To 4 g of poly(DLL-CLOH) dissolved in 20 mL of predried dichloromethane, was added 1.5 eq. of dry pyridine and was cooled to -5 C. A solution of ethylene chlorophosphate (0.5 mg) in 5 mL of dry chloroform was added dropwise and reacted for 2 h at -5 C. The resultant solution was allowed to reach 25 C. and react for 4 more h. The resulting solution was diluted with 50 mL dichloromethane, and then extracted with distilled water and a 1 M solution of NaHCO3. The organic phase was dried with sodium sulfate and filtered to yield poly(DLL-CLP). 3 g of poly(DLL-CLP) were dissolved in 30 mL of dry acetonitrile and cooled to -10 C. Approximately 300 mL of trimethylamine was condensed into the pressure vessel, which was then slowly heated to 60 C. The solution was stirred for 45 h at this temperature. The resulting polymer, a copolymer of d,l-lactide and caprolactone bearing phosphorylcholine pendant groups (poly(DLL-CLPC)), was precipitated in methanol and dried under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 19% 2: 43% 3: 17% 4: 11% | With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 50℃; for 2h; ruthenium(II) catalyzed reaction of 1,4-endoperoxide; | |
1: 17 % Chromat. 2: 11 % Chromat. 3: 43 % Chromat. 4: 19 % Spectr. | With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 50℃; for 2h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 21% 2: 17% 3: 28% 4: 5% | With cobalt(II) 5,10,15,20-tetraphenylporphyrin In chloroform at 60℃; for 11h; Further byproducts given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 44 % Chromat. 2: 4 % Chromat. 3: 39 % Chromat. | With tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 60℃; for 5h; other reagent; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With toluene-4-sulfonic acid In benzene for 4.6h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With pyridine; In dichloromethane; at 45℃; for 4h;Inert atmosphere; Schlenk technique; | General procedure: In a precursor step, 1.5 mL of <strong>[13482-22-9]4-hydroxylcyclohexanone</strong> (15 mmol) were synthesized7 and dissolved directly under argon atmosphere in 150 mL dried dichloromethane in a 250 mL one-necked round-bottom flask. Afterwards, 2.4 mL of pyridine (30 mmol) and the corresponding acid chloride (1.1 equiv) were added. The reaction mixture was stirred and heated up to 45 C. The esterification was performed under stirring for 4 h at 45 C. After cooling down to room temperature the solution was extracted three times with a HCl/water solution (2.3 mL HCl (1 N), 100 mL deionized water). The organic phase was dried over sodium sulfate and filtered. The solvent was removed under vacuum and the esters purified by column chromatography (methyl-tert-butyl ether/hexane 8:1). Only the cyclohexanone esters 15-17 could be isolated as crystalline solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1H-imidazole; In dichloromethane; | <strong>[13482-22-9]4-hydroxycyclohexanone</strong> (500 mg, 4.38 mmol), TBS-C1 (792 mg, 5.26 mmol),and imidazole (447 mg, 6.57 mmol) were dissolved in DCM (8761 tL) for 3 hours. The reaction mixture was diluted with DCM, washed with water, 1 N HC1, saturated NaHCO3, then brine, dried (Na2504), filtered, and concentrated in vacuo to give Intermediate 140Aas alight yellow oil: ?H NMR (400MHz, CHLOROFORM-cl) 4.09 (if, J=5.1, 2.7 Hz, 1H), 2.69-2.56 (m, 2H), 2.24-2.14 (m, 2H), 1.99-1.77 (m, 4H), 0.88 (s, 9H), 0.06 (s, 6 H). | |
40.4 g | With dmap; triethylamine; In N,N-dimethyl-formamide; at 10 - 35℃; for 16h; | To a solution of the crude <strong>[13482-22-9]4-hydroxycyclohexan-1-one</strong> (21.2 g), 4-dimethylaminopyridine (7.48 g) and triethylamine (22.5 g) in DMF (350 mL) was slowly added tert-butyldimethylsilyl chloride (30.2 g) at room temperature, and the mixture was stirred at room temperature for 16 hr. Water was added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was passed through a silica gel pad (ethyl acetate/hexane) to give the crude title compound (40.4 g). 1H NMR (300 MHz, CDCl3) delta 4.13 (tt, J=5.0, 2.5 Hz, 1H), 2.58-2.76 (m, 2H), 2.17-2.31 (m, 2H), 1.81-2.05 (m, 4H), 0.92 (s, 9H), 0.10 (s, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87 % Chromat. | With hydrogen In isopropyl alcohol at 100℃; various catalyst, var. temp., var. of hydrogen pressure, var. of substrate concentr.; | |
With hydrogen at 130℃; | ||
With Zr -F-100 In isopropyl alcohol at 82℃; for 6h; |
With nicotinamide adenine dinucleotide phosphate; isopropyl alcohol In aq. phosphate buffer at 30℃; for 12h; Enzymatic reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With water; toluene-4-sulfonic acid; In tetrahydrofuran; at 110℃; | A solution of the title compound (11 g, 70 mmol) in THF:H2O (100 mL, 1:1) was heated at 110 C. overnight. The reaction mixture was extracted with ethyl acetate (250 mL). The organic phase was washed with water and brine and dried over Na2SO4. The solvent was removed under reduced pressure to give the title compound (5.2 g, 65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With pyridine; at 0 - 20℃; for 12.5h;Inert atmosphere; | General procedure: 4-Hydroxy-cyclohexanone 1 (2.0 mmol) was dissolved in 3 mL of pyridine at 0 C. The corresponding acid chloride 2 (1.5 equiv) was added drop-wise at this temperature over a period of 30 min. After stirring for 12 h at room temperature, the mixture was directly poured on a column of silica gel and purified by flash chromatography (hexane/ethyl acetate 1:1). The esters 3-16 were isolated as colorless oils in analytically pure form in the yields given in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With triethylamine; In dichloromethane; at 20℃; for 16h;Inert atmosphere; | Step 1. Preparation of 4-oxocyclohexyl methanesulfonate Methanesulfonyl chloride (0.746 rnL, 9.64 mmol) and triethylamine (1.343 mL, 9.64 mmol) were added to a solution of <strong>[13482-22-9]4-hydroxycyclohexanone</strong> (1 g, 8.76 mmol) in dichloromethane (10 mL). The reaction mixture was stirred at rt for 16 h. The mixture was concentrated and the product was purified by column chromatography on silica gel (0% hexanes? 60% 9: 1 acetone:methanol/40% hexanes, 80 g column, lambda = 220 nm) to afford 4-oxocyclohexyl methanesulfonate (1.65 g, 8.58 mmol, 98% yield) as a colorless oil: XH MR (400MHz, CHLOROFORM-d) delta 5.14 (tt, J=5.5, 2.8 Hz, 1H), 3.1 1 (s, 3H), 2.75 - 2.59 (m, 2H), 2.49 - 2.28 (m, 4H), 2.24 - 2.06 (m, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air; methyl nitrite; nitrogen(II) oxide at 24.85℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With pyridine; at 0 - 20℃; for 12.5h;Inert atmosphere; | General procedure: 4-Hydroxy-cyclohexanone 1 (2.0 mmol) was dissolved in 3 mL of pyridine at 0 C. The corresponding acid chloride 2 (1.5 equiv) was added drop-wise at this temperature over a period of 30 min. After stirring for 12 h at room temperature, the mixture was directly poured on a column of silica gel and purified by flash chromatography (hexane/ethyl acetate 1:1). The esters 3-16 were isolated as colorless oils in analytically pure form in the yields given in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With Candida parapsilosis ATCC 7330 whole cells; In ethanol; water; at 25℃; for 8h;pH 6.8;Microbiological reaction; | General procedure: At first, 10 g of wet cells of Candida parapsilosis ATCC 7330 suspendedin 10 mL of water, and 40 mg (0.2 mmol) of benzil 1a dissolvedin 1 mL of dioxane (for other diketones ethanol was used) asa cosolvent were added into the cell suspension and incubated at25 C, 200 rpm for 8 h in a water bath shaker. The reaction was carriedout in triplicate. Control experiments were carried out in parallel without the whole cells and with heat treated cells underidentical conditions. In order to determine the isolated chemicalyield, the asymmetric reduction of 1a was carried out with80 mg of the substrate, wet cells and cosolvent were taken accordingly. After completion of the reaction the product 2a was extracted with ethyl acetate (3 10 mL) and the organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product obtained was purified by column chromatographyusing hexane/ethyl acetate (75:25) as the mobile phase to give 2a in 75% yield as a colourless solid. The ee was foundto be 98%, as determined by HPLC OD-H column using 9:1 hexane/isopropanol mixture. The specific rotation of 2a [a]D25 = +71.2 (c0.25, acetone) for 98% ee} was compared with the literature value to assign the absolute configuration, and it was found be (S). The same procedure was followed for the remaining diketones 1b-1j. The spectroscopic data of 2a, 2b, 2c, 2d, 2e, 2g and2h were in accordance with the literature values. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | Example 226: Synthesis of N -cyclopropyl- N -(( Z )-4-hydroxycyclohexyl)-6-(piperidin-1-yl)picolinamide and N -cyclopropyl- N -(( E )-4-hydroxycyclohexyl)-6-(piperidin-1-yl)picolinamide [554] [555] Step 1: Synthesis of 4-hydroxycyclohexanone [556] 1,4-cyclohexandione mono-ethylene ketal (1.0 g, 6.4 mmol) was dissolved in MeOH (30 ml), followed by addition of sodium borohydride (750 mg, 19.2 mmol) at 0oC, and then the resulting mixture was stirred at room temperature under nitrogen stream for 2 hours. The resulting reaction liquid was concentrated under reduced pressure, followed by addition of a saturated aqueous sodium chloride solution (30 ml), and extracted with EtOAc (50 ml x 2). The organic layer was dried over anhydrous sodium sulfate, and then filtered, concentrated, and vacuum-dried. The residue thus obtained was dissolved in THF (30 ml), followed by addition of 1N aqueous HCl solution (15 ml), and then the resulting mixture was stirred at room temperature for 18 hours. The resulting reaction liquid was neutralized by addition of 10% aqueous NaOH solution, followed by extraction with MC (30 ml x 3). The organic layer was dried over anhydrous sodium sulfate, followed by filtration and concentration, and then the residue thus obtained was subjected to MPLC (60% EtOAc/Hexanes), to obtain 450 mg of colorless oil (62%).[557] | |
24.8 g | To a solution of 1,4-dioxaspiro[4.5]decan-8-one (50.0 g) in MeOH (230 mL) was added portionwise sodium borohydride (9.50 g) at 0 C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure to a volume of ca. 70-80 mL. To the resulting solution was carefully dropwise added 2 M hydrochloric acid (200 mL) at 0 C., and the mixture was stirred at room temperature for 72 hr. An aqueous potassium carbonate solution was carefully added to the mixture, and the mixture was extracted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was passed through a silica gel pad (ethyl acetate) to give the crude title compound (24.8 g). 1H NMR (300 MHz, CDCl3) delta 4.20 (td, J=6.6, 3.0 Hz, 1H), 2.52-2.69 (m, 2H), 2.23-2.39 (m, 2H), 1.89-2.13 (m, 4H), 1.68 (d, J=3.4 Hz, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: (i), (ii) CrO3, H2SO4 2: (i) CF3CO2H, (ii) H2, Pd-C | ||
Multi-step reaction with 2 steps 1: 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate; tetrabutylammomium bromide / acetonitrile / 25 °C 2: [nickel(II)(pyridine)4(chloride)2]; 4,4'-di-tert-butyl-2,2'-bipyridine; pyridine; zinc; magnesium chloride / acetonitrile; N,N-dimethyl acetamide / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With acetic acid; In ethanol; at 20℃; for 3h;Heating / reflux; | EXAMPLE 9; 6-Methoxy-2,3,4,9-tetrahydro-l.ff-carbazol-3-ol [Compound No. 91; 4-Methoxyphenylhydrazine (0.644 g, 3.688 mmol) was suspended in acetic acid (20 mL) and ethanol (10 mL). 4-Hydroxycyclohexanone (0.420 mg, 3.688 mmol) was dissolved in acetic acid (10 mL) and then added to the reaction mixture at room temperature, with stirring. The reaction mixture was heated under reflux for 3 hours. The solvents were partially removed under reduced pressure and then the reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (2x50 mL). The organic layers were collected and dried (MgSO4), and the solvents were removed under reduced pressure to give a brown oil. The crude product was purified by column chromatography using silica gel and (ethyl acetate/n-hexane Vz). Fractions containing the required material were collected and the solvent removed under reduced pressure to give the product as a fine crystalline material (661 mg, 83%), mpl00-103C [CW. Bird, A.G.H. Wee, J.Heterocycl.Chem., 1985, 22, 191-192, mpl03-106C], RF=0.17 (ethyl acetate/n-hexane 1/1). IR (KBr): 3392, 2916, 2841, 1622, 1590, 1483, 1436, 1214, 1176, 1050, 1020, 830, 798 cm."1 1H NMR (CDCl3): 7.6O(1H. br), 7.19(1H, d, J=8.7Hz), 6.92(1H, d, J=2.4Hz), 6.81(1H, dd, J=2.4 & 8.71Hz), 4.29(1H, m), 3.86(3H, s), 3.09-2.67(4H, m), 2.11-2.02(2H, m), 1.75(1H5 br). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With trimethylamine at 25℃; for 2h; | 2 A 100 g 1,4-hexanediol was dissolved in 1.4 L of a mixture of acetonitrile and water (7:3 by volume). A mixture of 45.4 g of sodium bromate and 16.5 g of ammonium cerium (IV) nitrate was slowly added. The reaction was maintained under reflux conditions for 90 min. Once acetonitrile was removed by rotary evaporation, the solution was diluted with 800 mL of water and continuously extracted with chloroform for 72 h. The organic solution was dried over magnesium sulfate. Finally chloroform was evaporated from the organic solution to yield 99.5 g of a colorless oil (4-hydroxycyclohexanone). 130 g of benzyl chloride were slowly added to a solution of 60 g of 4-hydroxycyclohexanone in 400 mL of triethylamine. The solution was left to react at 25 ° C. for 2 h. After removal of the solvent, the product was purified by column chromatography to yield 100 g of a white powder 4-benzylestercyclohexanone. To a solution of 20 g 3-chloroperoxybenzoic acid in 200 mL of chloroform was added a solution of 15 g of 4-benzylestercylohexanone in 100 mL of chloroform. The reaction proceeded at 25° C. for 14 h. The solution was passed through Celite, extracted with brine and water successively. The solution was dried over magnesium sulfate and the solvent evaporated. Finally, the product was re-crystallized from a solution of ethyl acetate:hexane (1:4) to yield 7 g of white powder, benzylester protected 4-hydroxylcaprolactone (p-CLOH). 50 mg of 1,6-hexandiol, 20 g of D,L lactide (DLL) monomer and 4 g of p-CLOH were dried by azeotropic distillation of toluene. The monomers were heated to 140° C. to add stannous octoate (0.5 mol %) under a blanket of argon. The reaction was left to proceed at 160° C. for 14 h. The resulting polymer poly(DLL-pCLOH) was dissolved in acetone, precipitated in methanol and dried under reduced pressure. The benzyl protecting group was removed by dissolving 10 g of poly(DLL-pCLOH) in 100 ml of anhydrous ethyl acetate and adding 0.8 g of tin(IV) chloride under a blanket of argon. The reaction proceeded at 25° C. for 90 min. The resulting polymer poly(DLL-CLOH) was precipitated in methanol and dried under reduced pressure. To 4 g of poly(DLL-CLOH) dissolved in 20 mL of predried dichloromethane, was added 1.5 eq. of dry pyridine and was cooled to -5° C. A solution of ethylene chlorophosphate (0.5 mg) in 5 mL of dry chloroform was added dropwise and reacted for 2 h at -5° C. The resultant solution was allowed to reach 25° C. and react for 4 more h. The resulting solution was diluted with 50 mL dichloromethane, and then extracted with distilled water and a 1 M solution of NaHCO3. The organic phase was dried with sodium sulfate and filtered to yield poly(DLL-CLP). 3 g of poly(DLL-CLP) were dissolved in 30 mL of dry acetonitrile and cooled to -10° C. Approximately 300 mL of trimethylamine was condensed into the pressure vessel, which was then slowly heated to 60° C. The solution was stirred for 45 h at this temperature. The resulting polymer, a copolymer of d,l-lactide and caprolactone bearing phosphorylcholine pendant groups (poly(DLL-CLPC)), was precipitated in methanol and dried under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
24% | With pyridine hydrogenfluoride at 0℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With carbon dioxide; hydrogen at 50℃; for 4h; Supercritical conditions; | ||
With hydrogen In water at 25℃; for 7h; Autoclave; | ||
With hydrogen In dichloromethane at 50℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With Pd/Al2O3; hydrogen; In water; at 59.84℃; under 760.051 Torr; for 5h; | General procedure: In a typical reaction procedure, 4g Pd catalyst was added to a stirred solution composed of a given amount of phenol (Pd/phenol=0.02, 0.012 and 0.023 (ratio of mole)) and 50mL solvent in a modified 100mL three-necked flask with a jacket connected to a cooling recirculator (Scientz DL-3020) at 333K. The flask which contained the reaction mixture was purged 6 times with hydrogen in order to remove air completely before being stirred vigorously under atmospheric hydrogen. The products and reactants were analyzed by GC(GC2060 equipped PEG-20M column and flame ionization detector). | |
With hydrogen; In dichloromethane; water; at 100℃; under 1500.15 Torr; for 12h;Autoclave; | General procedure: A typical procedure for the hydrogenation of phenol was as follows: phenol (47mg, 0.5mmol), Pd/TiN (2.5-5 mol%) and H2O (2mL), CH2Cl2 (1mL), were placed into a 50mL stainless steel autoclave. The reactor system was purged with N2 three times followed by H2 three times. The autoclave was pressurized with 0.2MPa of H2. The reaction mixture was stirred vigorously at the desired reaction temperature. After a prescribed reaction time, the autoclave was cooled to room temperature and the residue gas was released. The catalyst was removed from the liquid by filtration, and then the organic phase was extracted. The conversion and selectivity were determined by a GC 112A equipped with a FID detector and an SE-54 column (30m×0.25mm×0.25mum film thickness). | |
With hydrogen; In dichloromethane; at 80℃; under 7500.75 Torr; for 3h; | General procedure: The hydrogenation reaction was carried out in the stainless steel reactor equipped with a magnetic stirrer. Amounts of phenol, Pd/C-HPA and solvent were added into the reactor. The reactor was ushed with 0.2MPa H2 for five times to remove air and 1.0MPa H2 was introduced. Then the mixture was heated to a desired temperature and reacted for a certain time. After the reaction was nished, the reactor was cooled to room temperature and depressurized. The reaction mixture was centrifuged to separate the catalysts and got the product mixture. The separated catalysts were directly used in the recycle experiments. The sample of the upper layer were characterized qualitatively with HP6890/5973 GC/MS equipped with an HP-5MS column, 30m × 0.25mm × 0.25mum, and its quantitative analysis were determined by GC using HP6890 GC equipped with an HP-5 column, 30m × 0.32mm × 0.25mum. The contents of the reactants and products were directly showed by the system of GC chemstation according to the area of each chromatograph peak. The conversion of phenol was dened as Conv.%, which was the wt% of phenol consumed in the reaction. The selectivity of one product was calculated by Sel.% = Wp/Wall × 100, where Wp was the mass of one product, and Wall was the total mass of all products, including cyclohexanone and cyclohexanol. All the experiments were repeated for five times to conrm the results eectiveness. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | Step 2: Synthesis of 4-(cyclopropylamino)cyclohexanol [558] <strong>[13482-22-9]4-hydroxycyclohexanone</strong> (443 mg, 3.88 mmol) was dissolved in 1,2-dichloroethane (20 ml), followed by sequential addition of cyclopropylamine (0.295 ml, 4.27 mmol), NaBH(OAc)3 (1.3 g, 6.21 mmol), and acetic acid (0.2 ml, 3.88 mmol), and then the resulting mixture was stirred at room temperature under nitrogen stream for 13 hours. The resulting reaction liquid was neutralized by addition of 10% aqueous NaOH solution, and extracted with 10% MeOH/MC (15 ml x 4). The organic layer was dried over anhydrous sodium sulfate, followed by filtration, concentration, and vacuum drying, to obtain 580 mg of yellow solid (96%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With pyridine; at 0 - 20℃; for 12.5h;Inert atmosphere; | General procedure: 4-Hydroxy-cyclohexanone 1 (2.0 mmol) was dissolved in 3 mL of pyridine at 0 C. The corresponding acid chloride 2 (1.5 equiv) was added drop-wise at this temperature over a period of 30 min. After stirring for 12 h at room temperature, the mixture was directly poured on a column of silica gel and purified by flash chromatography (hexane/ethyl acetate 1:1). The esters 3-16 were isolated as colorless oils in analytically pure form in the yields given in Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With caesium carbonate; In 1,4-dioxane; at 80℃; for 18h; | To a solution of 4-hydroxycyclohexanone (171 mg, 1.5 mmol) in dloxane was added Cs2CO3 (488 mg, 1.5 mmol) and <strong>[1379338-74-5]5,7-dichloropyrido[4,3-b]pyrazine</strong> (200 mg, 1.0mmo) at room temperature. The mixture was stirred at 80 C for 18 hours. After that,the <strong>[1379338-74-5]5,7-dichloropyrido[4,3-b]pyrazine</strong> was consumed and the reaction was used for next step directly. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With toluene-4-sulfonic acid; In ethanol; at 20℃; | Reference Example 14 [0451] Step 1 [0452] To a solution of <strong>[13482-22-9]4-hydroxycyclohexanone</strong> (2.0g, 17.5mmol) in ethanol (8ml) were added triethyl orthoformate (8.78ml, 52.6mmol) and p-toluenesulfonic acid monohydrate (3.3mg, 0.018mmol), and the mixture was stirred overnight at room temperature. To the reaction mixture was added saturated aqueous sodium bicarbonate, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give Compound vii-7 (2.93g, Yield 89%). [0453] 1H-NMR(CDCl3)delta:1.15-1.21 (m, 6H), 1.49-1.60 (m, 4H), 1.76-1.81 (m, 2H), 1.93-2.00 (m, 2H), 3.43-3.50 (m, 4H), 3.77 (brs, 1H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.5% | a) (E)-10-(ethyl(4-hydroxycyclohexyl)amino)-l-methoxy-3-methyl-5,6,15,16- tetr ahydr obenzo [c] pyrido [4,3-j ] [1] azacyclododecin-14(9H)-one To (E)-10-amino-l-methoxy-3-methyl-5,6, 15,16-tetrahydrobenzo[c]pyrido[4,3- j][l]azacyclododecin-14(9H)-one (0.177 g, 0.525 mmol) and <strong>[13482-22-9]4-hydroxycyclohexanone</strong> (0.120 g, 1.049 mmol) was added DCE (7 mL) and the suspension was stirred for 10 min. AcOH (0.120 mL, 2.098 mmol) and Na(OAc)3BH (0.445 g, 2.098 mmol) were added and the reaction was stirred vigorously at room temperature overnight. Acetaldehyde (0.148 mL, 2.62 mmol) was added and the reaction was allowed to stir for 1 h. The reaction was diluted into DCM (25 mL) with stirring, then water and saturated aqueous NaHC03 solution were added and the biphasic system was stirred for 30 min. This was then separated and back extracted with DCM. The combined organics were dried over MgS04, filtered and concentrated in vacuo to a residue that was adsorbed onto silica gel and purified via flash column chromatography using (Isco Rf-12 gram column, 10-60 % (3 : 1 EtOAc:EtOH) in heptane) to afford a mixture of cis and trans cyclohexyl isomers of (E)- 10-(ethyl(4-hydroxycyclohexyl)amino)-l-methoxy-3-methyl-5,6,15, 16- tetrahydrobenzo[c]pyrido[4,3-j][l]azacyclododecin-14(9H)-one (185 mg, 0.391 mmol, 74.5 % yield) as a solid. LC-MS(ES) 464.2 [M+H]+ (minor), 183.5 (major). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With sulfuric acid; acetic acid; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 15mL of glacial acetic acid was treated with 4 drops of concentrated sulfuric acid. This mixture was left to stand at room temperature until the starting materials couldn?t be detected on the TLC plate. The reaction mixture was then diluted with 100 mL water. After 10 min stirring the yellow solid was collected on a glass filter, treated with 25ml of 5% aqueous solution of potassium hydrogencarbonate and washed with water. The yellow solid was dried and recrystallized from a suitable solvent. (2E,6E)-2,6-Bis(4?-nitrobenzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6f) Overall yield: 85%. Mp: 216-218C (MeOH/CHCl 3 ); Lit.: 210-213C [42]. 1 H-NMR (500MHz, CDCl 3 ) delta (ppm) 3.06-3.18 (br m, 4H), 5.21 (m, 1H), 7.59 (d, J = 9.0Hz, 4H), 7.92 (s, 2H), 8.29 (d, J = 9.0Hz, 4H). 13 C-NMR (125MHz, CDCl 3 ) delta (ppm) 32.9, 66.9, 123.8, 130.7, 134.1, 137.4, 141.4, 147.6, 187.2. MS: m/z calculated for C 20 H 16 N 2 O 6 : see Table1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In water at 25℃; for 15h; Schlenk technique; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.35 g | With sodium tris(acetoxy)borohydride; In 1,2-dichloro-ethane; for 0.5h; | 4-hydroxycyclohexanone (1.25 g, 11.00 mmol) and tert-butyl 4- (aminomethyl)benzoate (2.3 g, 11.0 mmol) was dissolved in 1,2-dichloroethane (50 mL) was added sodium (triacetoxy)borohydride (2.33 g, 11.0 mmol). After 30 min, potassium carbonate (1M aqueous) was added, followed by methylene chloride. The organic phase was isolated, washed with brine and evaporated under pressure to afford residue tert-butyl 4-(((4- hydroxycyclohexyl)amino)methyl)benzoate (3.35 g, 10.9 mmol) was obtained in quantitative yield. LCMS (ESI+): 306.2 (M+H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In methanol; at 40℃; for 1h; | A solution of <strong>[13482-22-9]4-hydroxycyclohexanone</strong> (3.5 g, 30.7 mmol) and 2-methylpropan-l- amine (3.35 ml, 33.7 mmol) in MeOH (61.3 ml) was heated at 40 C for 1 hour, then allowed to cool to room temperature. Sodium borohydride (1.740 g, 46.0 mmol) was added slowly. The reaction was allowed to stir at room temperature overnight. The solvent was evaporated and the crude material was taken up in EtOAc and H2O. Layers were separated. The aqueous phase was extracted with EtOAc (2X). The combined organic phases were dried over Na2S04, filtered, and concentrated to afford 152A (4.0 g, 23.35 mmol, 76 % yield) as a colorless oil. 1H MR (400MHz, chloroform-d) delta 5.30 (s, 1H), 3.87 (br. s., 1H), 3.61 (br. s., 1H), 2.50 (d, J=3.8 Hz, 1H), 2.41 (dd, J=6.7, 2.0 Hz, 2H), 2.07 - 1.87 (m, 2H), 1.80 - 1.66 (m, 2H), 1.67 - 1.50 (m, 3H), 1.39 - 1.22 (m, 1H), 1.22 - 1.05 (m, 1H), 0.96 - 0.85 (m, 6H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With pyridine; In dichloromethane; at 45℃; for 4h;Inert atmosphere; Schlenk technique; | General procedure: In a precursor step, 1.5 mL of <strong>[13482-22-9]4-hydroxylcyclohexanone</strong> (15 mmol) were synthesized7 and dissolved directly under argon atmosphere in 150 mL dried dichloromethane in a 250 mL one-necked round-bottom flask. Afterwards, 2.4 mL of pyridine (30 mmol) and the corresponding acid chloride (1.1 equiv) were added. The reaction mixture was stirred and heated up to 45 C. The esterification was performed under stirring for 4 h at 45 C. After cooling down to room temperature the solution was extracted three times with a HCl/water solution (2.3 mL HCl (1 N), 100 mL deionized water). The organic phase was dried over sodium sulfate and filtered. The solvent was removed under vacuum and the esters purified by column chromatography (methyl-tert-butyl ether/hexane 8:1). Only the cyclohexanone esters 15-17 could be isolated as crystalline solids. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With pyridine; In dichloromethane; at 45℃; for 4h;Inert atmosphere; Schlenk technique; | In a precursor step, 1.5 mL of <strong>[13482-22-9]4-hydroxylcyclohexanone</strong> (15 mmol) were synthesized7 and dissolved directly under argon atmosphere in 150 mL dried dichloromethane in a 250 mL one-necked round-bottom flask. Afterwards, 2.4 mL of pyridine (30 mmol) and the corresponding acid chloride (1.1 equiv) were added. The reaction mixture was stirred and heated up to 45 C. The esterification was performed under stirring for 4 h at 45 C. After cooling down to room temperature the solution was extracted three times with a HCl/water solution (2.3 mL HCl (1 N), 100 mL deionized water). The organic phase was dried over sodium sulfate and filtered. The solvent was removed under vacuum and the esters purified by column chromatography (methyl-tert-butyl ether/hexane 8:1). Only the cyclohexanone esters 15-17 could be isolated as crystalline solids. 5.4.1. 4-Oxo-cyclohexyl 4-nitrobenzoate (15) Rf = 0.77 (hexane/dichloromethane 1:4); 1H NMR (300 MHz, CD2Cl2, ppm) delta = 8.25 (d, 2H, 11-H, 15-H), 8.15 (d, 2H, 12-H, 14-H), 5.41 (sept, 1H, 4-H), 2.55 (m, 2H, 2-H, 6-H), 2.4 (m, 2H, 3-H, 5-H), 2.31-2.16 (m, 4H, 3-H, 5-H, 2-H, 6-H); 13C NMR (75 MHz, CD2Cl2, ppm) delta = 209.2 (C-1), 164.1 (C-8), 150.9 (C-13), 135.7 (C-10), 130.7 (C-11, C-15), 123.7 (C-12, C-14), 70.5 (C-4), 37.2 (C-2, C-6), 30.4 (C-3, C-5). IR (solid): nu = 3107, 2956, 1720, 1524, 1274, 1119, 874 cm-1 elemental analysis calculated (%) for C13H13O5N (262.91): C 59.3, H 4.9, N 5.3; found: C 59.4, H 4.96, N 5.1. MS (ESI): m/z calculated for C13H13O5N: [M+H]+: 263.0794; found: 263.0780. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide In acetonitrile at 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: cyclohexane With 2C60H50O21Si10(12-)*9Cu(2+)*6Na(1+); water; dihydrogen peroxide; nitric acid; oxygen-18 In acetonitrile at 60℃; Stage #2: With triphenylphosphine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: phenylmagnesium bromide / tetrahydrofuran 2: water; acetone 3: trifluoroacetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
12% | With ammonium chloride In dimethyl sulfoxide at 50 - 70℃; | 6.1 1,2,2,6,6-pentamethyl-4-piperidone (0.5-2 eq), 4-hydroxycyclohexanone (3-6eq)And NH4Cl (3- 6 eq) dissolved in DMSO,And heating and stirring at 50-70 ° C for 6-12 hours. Acidified with dilute hydrochloric acid,Extract with petroleum ether and adjust pH=9 with saturated sodium carbonate solution.Concentration under reduced pressure gave a crude product which was purified using purified.The mobile phase was 5% MeOH / DCM to give the product as a white solid.The yield was 12%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | To a solution of 4-hydroxy-1-cyclohexanone (8) (200 mg, 1.75 mmol) in dry CH2Cl2 (15 ml) at -35 C was added separately a solution of TiCl4 (0.29 ml, 2.62 mmol) and tributylamine (1.25 ml, 5.25 mmol) in CH2Cl2 (2 ml each). The reaction mixture was stirred at the same temperature for half an hour and after which a solution of 1,1-dimethoxyacetone (0.42 ml, 3.5 mmol) in CH2Cl2 (2 ml) was added to it. Reaction mixture was allowed to attain room temperature on its own and left to stir for 3 hours. Water (20 ml) was added to quench the reaction mixture. Extraction was done with CH2Cl2 (3 x 15 ml) and the combined organic layer was washed with brine (40 ml), dried over anhydrous Na2SO4 (2 g) and evaporated to dryness under reduced pressure. Crude product was purified with column chromatography using ethyl acetate/hexanes (5:95). The product was obtained as a colorless liquid in 78% yield (180 mg). IR (neat) 3054, 2930, 1588, 1449, 1281, 1184, 1086, 855, 742 cm-1; 1H NMR (CDCl3, 500 MHz): delta 2.21 (s, 3H), 7.20-7.28 (m, 2H), 7.37 (s, 1H), 7.43 (d, 1H, J = 8.0 Hz), 7.49 (d, 1H, J = 7.5 Hz); 13C NMR (CDCl3, 125 MHz): delta 8.0, 111.4, 115.7, 119.5, 122.3, 124.2, 129.1, 141.4, 155.4; HRMS calcd. for C9H8ONa [M+Na]+: 155.0473. Found 155.0477. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) Overall yield: 88%. Mp: 139-140 C (MeOH). 1 H-NMR (500 MHz, CDCl 3 ) delta (ppm) 1.94 (s, 1H), 2.98 (m, 2H), 3.19 (m, 2H), 4.12 (m, 1H), 7.45 (br m, 10H), 7.88 (s, 2H). 13 C-NMR (125MHz, CDCl 3 ) delta (ppm) 36.5, 65.6, 128.4, 128.8, 130.3, 132.3, 135.5, 139.3, 188.8. MS: m/z calculated for C 20 H 18 O 2 : see Table1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With potassium hydroxide; In methanol; water; at 20℃; | General procedure: A solution of 0.1 mol (1.141 g) <strong>[13482-22-9]4-hydroxycyclohexanone</strong> and 0.2 mol of the appropriate arylaldehyde in 20 mL of methanol was treated with a solution of 0.3 mol (1.683 g) potassium hydroxide in 20 mL of water. This mixture was stirred at room temperature on a magnetic stirrer until the starting materials couldn?t be detected on the TLC plate from the mother liquor. The reaction mix-ture was then diluted with 100mL water. The precipitated yellow solid was col-lected on a glass filter and washed with water. The yellow solid was dried, and recrystallized from a suitable solvent.(2E,6E)-2,6-Bis(benzylidene)-<strong>[13482-22-9]4-hydroxycyclohexanone</strong> (6a) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium tris(acetoxy)borohydride; acetic acid; In dichloromethane; at 20℃;Inert atmosphere; | General procedure: Taking Compound 5b as an example, the synthesis method was introduced as below: 77.5 mg (0.832 mmol) aniline and 95.0 mg (0.832 mmol) <strong>[13482-22-9]4-hydroxycyclohexan-1-one</strong> were dissolved in dichloromethane under argon, and 229.32 mg (1.082 mmol) sodium borohydride and 94.98 mg (0.749 mmol) acetic acid were added. The reaction was stirred at room temperature. After the reaction was completed monitored by TLC, the mixture was evaporated to dryness. Column chromatography (DCM/MeOH = 120:1 to 60:1) to obtain 135.3 mg intermediate 5a. Under argon, 135.3 mg (0.71 mmol) of intermediate 5a was dissolved in dichloromethane, and sodium bicarbonate (0.88 g (10.65 mmol)) and Dess-Martin reagent 0.59 g (1.42 mmol) were added and stirred at room temperature for 1.5 h. The reaction was quenched with EtOAc. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90.6% | With triethylamine; In dichloromethane; at 0 - 20℃; for 4h; | S1. After dissolving <strong>[13482-22-9]p-hydroxycyclohexanone</strong> (Formula C1, 20g, 175mmol) in dichloromethane (200mL), add triethylamine (36g, 356mmol) and place in an ice water bath to cool to 0C; , Slowly add acrylic acid chloride (15.9g, 176mmol) dropwise. After the dropwise addition, continue stirring at 0 degrees Celsius for 1 hour. Then, slowly increase the temperature to room temperature and continue stirring for 3 hours to carry out the reaction. After the reaction is complete, add the reaction solution It was quenched in ice water (100 mL), neutralized with saturated sodium bicarbonate solution, and extracted three times with dichloromethane (80 mL*3). The resulting organic phase was washed with saturated brine and dried over anhydrous sodium sulfate, and then vacuumed Spin dry to obtain the intermediate (formula C2, 27.6 g, 159 mmol, yield 90.6%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.6% | With magnesium(II) sulfate; toluene-4-sulfonic acid; In toluene;Inert atmosphere; Reflux; | To a solution of <strong>[5428-40-0]4-bromo-2-hydroxybenzamide</strong> (215 mg, 1.0 mmol), 4-hydroxycyclohexanone2c (0.15 mL, 1.3 mmol) and p-toluenesulfonic acid monohydrate(10 mg, 0.053 mmol) in toluene (4 mL), magnesium sulfate (240 mg,2.0 mmol) was added. The mixture was refluxed overnight. EtOAc(40 mL) was added and the solid was filtered off. The filtrate wasconcentrated under reduced pressure and the residue was purifiedby silica gel chromatography (0-100% EtOAc/hexane then 25%EtOH/EtOAc) as eluent to afford the title compound 2d (58 mg, yield18.6%) as white solid. |
18.6% | With magnesium(II) sulfate; toluene-4-sulfonic acid; In toluene;Inert atmosphere; Reflux; | To a solution of <strong>[5428-40-0]4-bromo-2-hydroxybenzamide</strong> (215 mg, 1.0 mmol), 4-hydroxycyclohexanone2c (0.15 mL, 1.3 mmol) and p-toluenesulfonic acid monohydrate(10 mg, 0.053 mmol) in toluene (4 mL), magnesium sulfate (240 mg,2.0 mmol) was added. The mixture was refluxed overnight. EtOAc(40 mL) was added and the solid was filtered off. The filtrate wasconcentrated under reduced pressure and the residue was purifiedby silica gel chromatography (0-100% EtOAc/hexane then 25%EtOH/EtOAc) as eluent to afford the title compound 2d (58 mg, yield18.6%) as white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dihydrogen peroxide; HNO3; [Cu0.152Mn0.848(μ-pyridine-2,6-dicarboxylato)2{Na2(μ-H2O)4}]n·nH2O In water monomer; acetonitrile at 75℃; for 8h; Green chemistry; | 2.4. Catalytic studies General procedure: The selective peroxidative oxidation of cyclohexane to cyclohexanoland cyclohexanone was carried out under air and atmospheric pressureusing polymer 1 as a catalyst. The desired amount of polymer 1 (0.5-10μmol) was mixed with cyclohexane (1.00 mmol); acetonitrile (3 mL) andHNO3 as an acid promoter (additive) with the molar ratio n(HNO3)/n(catalyst) (0-20) in a 50 mL round bottom flask. An aqueous solution ofH2O2 (30%) as an oxidizing agent with the molar ratio n(H2O2)/n(catalyst) (50-350) was then added. The resulting solution was vigorouslystirred for 1-10 h at 25-105 °C. After completion of the desiredreaction time, 90 μL of cycloheptanone (as GC internal standard) and 10mL of diethyl ether (for substrate and organic product extraction) and1.0 g PPh3 (for reduction of cyclohexyl hydroperoxide to cyclohexanol ifformed) were added to the above-mentioned solution [33,34]. The reactionmixture was stirred with cooling at ca. 0 C and centrifuged foranalysis by GC. Gas chromatographic (GC) measurement was carried outusing a Hewlett-Packard 5890 series II gas chromatograph instrumentequipped with FID detector, and a DB-5 fused silica column (30 m 0.53mm i.d., film thickness 1.5 m). The helium was used as the carrier gas.The Gas Chromatography-Mass Spectrometry (GC-MS) analysis wasperformed on a Varian 3400(He as the carrier gas), equipped with a DB-5 column with the same characteristics that used in the GC instrument. Thecomposition products that were achieved from the catalytic peroxidativeoxidation reactions were characterized by comparing their retentiontimes and matched with those of commercially available materials. Themass spectra of obtained products were confirmed by fragmentationpatterns of the NIST spectral library stored in the computer software.Each test was repeated three times and the average of the results wasreported. Blank experiments were carried out without the catalyst toconfirm the catalytic performance of polymer 1. |
Tags: 13482-22-9 synthesis path| 13482-22-9 SDS| 13482-22-9 COA| 13482-22-9 purity| 13482-22-9 application| 13482-22-9 NMR| 13482-22-9 COA| 13482-22-9 structure
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