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[ CAS No. 117-99-7 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 117-99-7
Chemical Structure| 117-99-7
Chemical Structure| 117-99-7
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Product Details of [ 117-99-7 ]

CAS No. :117-99-7 MDL No. :MFCD00002216
Formula : C13H10O2 Boiling Point : -
Linear Structure Formula :- InChI Key :HJIAMFHSAAEUKR-UHFFFAOYSA-N
M.W : 198.22 Pubchem ID :8348
Synonyms :

Calculated chemistry of [ 117-99-7 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 2
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 58.34
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.01 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.19
Log Po/w (XLOGP3) : 3.52
Log Po/w (WLOGP) : 2.62
Log Po/w (MLOGP) : 2.34
Log Po/w (SILICOS-IT) : 2.92
Consensus Log Po/w : 2.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.75
Solubility : 0.0355 mg/ml ; 0.000179 mol/l
Class : Soluble
Log S (Ali) : -3.99
Solubility : 0.0204 mg/ml ; 0.000103 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.29
Solubility : 0.0101 mg/ml ; 0.0000511 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.4

Safety of [ 117-99-7 ]

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:

Application In Synthesis of [ 117-99-7 ]

* 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 [ 117-99-7 ]

[ 117-99-7 ] Synthesis Path-Downstream   1~88

  • 2
  • [ 85-19-8 ]
  • [ 117-99-7 ]
  • 3
  • [ 119-61-9 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
81% With palladium diacetate; bis-[(trifluoroacetoxy)iodo]benzene In 1,2-dichloro-ethane at 80℃; for 2h;
80% With palladium diacetate; Selectfluor; trifluoroacetic acid; trifluoroacetic anhydride at 100℃; for 3.5h; Sealed tube; regioselective reaction;
62% With dirhodium tetraacetate; Selectfluor; trifluoroacetic acid; trifluoroacetic anhydride at 70℃; for 10h; Sealed tube; regioselective reaction;
57% With iodobenzene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; tert-butylammonium hexafluorophosphate(V); trifluoroacetic acid; trifluoroacetic anhydride at 50℃; for 8h; Electrochemical reaction;
31% With dipotassium peroxodisulfate; palladium diacetate; trifluoroacetic acid; trifluoroacetic anhydride at 100℃; for 10h; regioselective reaction;
Multi-step reaction with 2 steps 1: bis-[(trifluoroacetoxy)iodo]benzene / 1,2-dichloro-ethane / 2 h / 80 °C 2: silica gel / hexane; dichloromethane
With water; copper(II) sulfate
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / toluene / 36 h / Dean-Stark; Reflux; Inert atmosphere 2: tetrakis(actonitrile)copper(I) hexafluorophosphate; dihydrogen peroxide / acetone; water / 0.5 h / 20 °C

  • 6
  • [ 117-99-7 ]
  • [ 100-39-0 ]
  • [ 93254-81-0 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate; potassium iodide In acetone Heating;
98% With caesium carbonate In acetonitrile at 50℃;
98% With caesium carbonate In acetonitrile at 50℃; Inert atmosphere;
With sodium methylate 1.) MeOH, 1 h, 2.) reflux, overnight; Yield given. Multistep reaction;
With potassium carbonate; potassium iodide In acetone at 50℃;

  • 8
  • [ 117-99-7 ]
  • [ 74-88-4 ]
  • [ 2553-04-0 ]
YieldReaction ConditionsOperation in experiment
96.9% With sodium hydroxide In dimethyl sulfoxide at 40℃;
95% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; 13.1 Synthesis of 13.1 (2-methoxy-phenyl)(phenyl)-methanone (2-Hydroxy-phenyl)(phenyl)-methanone (1.98 g, 10 mmol)Soluble in N,N-dimethylformamide (30ml),Add anhydrous potassium carbonate (2.76 g, 20 mmol),Stir at room temperature,Add methyl iodide (2.84 g, 20 mmol),The reaction was carried out for 6 h at room temperature.TLC monitoring,After the reaction is completed,Quenched with water,Extract with dichloromethane (3 x 30 ml).After combining the organic phases,Water,Washed with saturated saline,Drying the organic phase with anhydrous sodium sulfate,Rotating to remove the solvent,Purification by silica column chromatographyPetroleum ether/dichloromethane (4/1) elution,The product was obtained as a brown solid (yield: EtOAc) (yield: 95%).
95% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 6h; 17.1 17.1 Synthesis of (2-methoxyphenyl)(phenyl)-methanone (2-hydroxy-phenyl)(phenyl)-methanone (1.98 g, 10 mmol) is dissolved in N,N-dimethylformamide (30 mi); anhydrous potassium carbonate (2.76 g, 20 mmol) is added; the above materials are stirred at room temperature; then iodomethane (2.84 g, 20 mmol) is dropped; and the reaction is carried out for 6 h at room temperature. TLC is used for monitoring; after the reaction is completed, the materials are quenched by addition of water and extracted with dichloromethane (3×30 ml). After being merged, the organic phase is washed with water and a saturated salt solution, dried with anhydrous sodium sulfate, desolvated by the rotary evaporator, purified by silicon oxide column chromatography and eluted by ligroin/dichloromethane (4/1) to obtain 2.01 g of the brown solid product, with a yield of 95%. 1H NMR (400 MHz, CDCl3), δ: 7.82-7.80 (m, 2H), 7.57-7.53 (m, 1H), 7.49-7.41 (m, 3H), 7.37 (dd, J=1.6, 7.6 Hz, 1H), 7.04 (t, J=7.6 Hz, 1H), 6.98 (d, J=8.4 Hz, 1H), 3.73 (s, 3H).
85% With potassium phosphate In acetone for 3h; Heating;
With potassium carbonate at 100℃;

  • 9
  • [ 117-99-7 ]
  • [ 107-30-2 ]
  • [ 71103-99-6 ]
YieldReaction ConditionsOperation in experiment
91% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; 1.1 Method 4-2-1: General procedure: Take the methoxymethyl ether protecting group as an example.The 2-hydroxy-diaryl ketone compound 6 (10 mmol) was dissolved in dichloromethane (50 ml).Add diisopropylethylamine (30 mmol) and stir at room temperature.Chloromethyl methyl ether(20 mmol). Heated for 12 hours,TLC monitoring,After the reaction is completed.The reaction solution was cooled to room temperature.Rotating to remove the solvent,Purification by silica column chromatographyA 2-methoxymethoxy-diaryl ketone compound 5 can be obtained.
91% With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 12h; Reflux; 2.1 2.1 Synthesis of (2-methoxymethoxy-phenyl)(phenyl)methanone (2-hydroxy-phenyl)(phenyl)-methanone (1.98 g, 10 mmol) is dissolved in dichloromethane (50 ml), diisopropyl ethylamine (30 mmol) is added, the above materials are stirred at room temperature, and chloromethyl methyl ether (20 mmol) is added. The above materials are heated to reflux, for 12 hours, and the reaction is monitored by TLC until the reaction is completed. Tire reaction liquid is cooled to room temperature, the solvent is removed by rotary evaporation, and the product is purified by silica column chromatography to obtain 2.2 g of brown oily product of (2-methoxymethoxy-phenyl)(phenyl)-methanone (yield 91%). 1H NMR (400 MHz, CDCl3), δ: 7.84-7.82 (m, 2H), 7.58-7.54 (m, 1H), 7.47-7.42 (m, 3H), 7.37 (q, J=12.0 Hz, 1H), 7.21 (d, J=8.0 Hz, 1H), 7.12-7.09 (m, 1H), 5.05 (s, 2H), 3.29 (s, 3H).
With potassium carbonate In acetone
With potassium carbonate In acetone Reflux; II.1 1. Preparation of (2-(methoxymethoxy)phenyl)(phenyl)methanone To a stirring solution of 2-hydroxybenzophenone (3.0 g, 15.1 mmol) and K2CO3 (9.94 g, 71.9 mmol) in acetone (80 mL) under reflux was added MOMCl (2.9 mL, 37.8 mmol) and allowed to stir overnight. The reaction was then cooled to 23° C., diluted with EtOAc, washed with 2N NaOH (3*), the organic phase dried (Na2SO4), filtered and concentrated to provide the product (605 mg) as an oil: 1H NMR (400 MHz, DMSO-d6) δ ppm 7.67-7.72 (2H, m), 7.63 (1H, d, J=7.07 Hz), 7.48-7.54 (3H, m), 7.34 (1H, dd, J=7.33, 1.52 Hz), 7.24 (1H, d, J=8.34 Hz), 7.13 (1H, t, J=7.45 Hz), 5.08 (2H, s), 3.13 (3H, s).
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 25℃; for 18h;

  • 11
  • [ 117-99-7 ]
  • [ 14061-01-9 ]
YieldReaction ConditionsOperation in experiment
76% With isocyanate de chlorosulfonyle In toluene for 10h; Reflux; A mixture of 3a (100 mg, 0.5 mmol) was dissolved in toluene (10 mL), ClSO2NCO(70.8 mg, 43.4 mL, 0.5 mmol) was added. Then the reaction mixture was heated at reflux for 10 h. The reaction mixture was washed with H2O (10 mL). The organic layer was then dried over anhydrous Na2SO4, filtered and concentrated. The crude product was loaded on a silica gel column and flashed with 20% ethyl acetate in petroleum ether to afford the desired products 6 as solid.
76% With isocyanate de chlorosulfonyle In toluene at 80℃; for 10h;
72% With isocyanate de chlorosulfonyle In toluene at 100 - 105℃; for 3h;
70% With formic acid; isocyanate de chlorosulfonyle; sodium hydride In N,N-dimethyl acetamide; mineral oil at 0 - 50℃; Inert atmosphere; Neat (no solvent);
60% Stage #1: 2-Hydroxybenzophenone With sulphamoyl chloride In dichloromethane; N,N-dimethyl acetamide at 0 - 20℃; for 0.166667h; Inert atmosphere; Stage #2: With sodium hydride In dichloromethane; N,N-dimethyl acetamide; mineral oil at 50℃; for 1h;
Stage #1: 2-Hydroxybenzophenone With formic acid; isocyanate de chlorosulfonyle In N,N-dimethyl acetamide at 0 - 20℃; Cooling with ice; Stage #2: With sodium hydride In N,N-dimethyl acetamide; mineral oil at 20 - 50℃;
Stage #1: 2-Hydroxybenzophenone With sulphamoyl chloride In N,N-dimethyl acetamide at 20℃; Cooling with ice; Stage #2: With sodium hydride In N,N-dimethyl acetamide; mineral oil at 20 - 50℃; 4. Synthesis of Six-membered Cyclic Sulfonamides General procedure: Anhydrous formic acid (4.0 mmol) was added dropwise to neat chlorosulfonyl isocyanate (4.0 mmol) at 0 °C with rapid stirring. Vigorous gas evolution was observed during the addition process. The resulting white solid was stirred at room temperature until gas evolution ceased (1-2 h). To the resulting sulfamoyl chloride (ClSO2NH2) was added 2-hydroxybenzophenone derivatives 7a-j (2.0 mmol). After the mixture was cooled under ice-cooling, 3 mL of DMA (N, N-dimethyl-acetamide) was slowly added. After the ice-cooling was moved, the mixture was stirring for 10 min, and sodium hydride (96 mg of 60 % dispersion in mineral oil, 2.4 mmol) was added in portions. After stirring for 30 min at rt another sodium hydride (96 mg of 60 % dispersion in mineral oil, 2.4 mmol) was added in portions again. After stirring for 1 h at rt the reaction mixture was allowed to stir overnight (8-12 h) at 50 °C. The reaction was quenched by the addition of 5 mL of H2O and the aqueous layer was extracted with 3 x 10 mL of EtOAc. The combined organic layers were washed with 1 x 10 mL of H2O and 1 x 10 mL of brine, and concentrated under reduced pressure. Purification by chromatography on silica gel afforded (petroleum ether/EtOAc = 3/1) afforded the desired imines 4a-j as a white solid in 66~73% yield.

  • 14
  • [ 117-99-7 ]
  • [ 1119-51-3 ]
  • [ 121150-34-3 ]
YieldReaction ConditionsOperation in experiment
93% With potassium carbonate
6.91 g With potassium carbonate In acetonitrile at 50℃; for 22h; 60 Synthesis of intermediate 19a: General procedure: A mixture of 4-bromo-l -butene [CAS 5162-44-7] (10.2 mL, 101 mol), (2- hydroxyphenyl)(phenyl)methanone [CAS 117-99-7] (5 g, 25.224 mol) and K2CO3 (10.46 g, 75.673 mol) in CH3CN (66 mL) was stirred at 50°C for 18 h. The reaction was not complete and 4-bromo-l -butene (7.0 mL, 70 mmol) was added again. The mixture was stirred for another 24 h at 50°C. The mixture was filtered and concentrated under reduced pressure. The residue was purified by flash chromatography over silica gel (20-45 pm, 120 g, heptane/EtOAc 90/10). The pure fractions were collected and concentrated to dryness under reduced pressure to give (2-(but-3-en-l-yloxy)phenyl)(phenyl)methanone (intermediate 19a, 2 g).
  • 15
  • [ 117-99-7 ]
  • [ 644-97-3 ]
  • [ 77086-08-9 ]
YieldReaction ConditionsOperation in experiment
80.5% With triethylamine In tetrahydrofuran -78 deg C -> 25 deg C;
  • 16
  • [ 117-99-7 ]
  • [ 106-95-6 ]
  • [ 121150-32-1 ]
YieldReaction ConditionsOperation in experiment
100% With potassium carbonate In acetone at 50℃; Step 2: 2-(Allyloxy)-4,6-dimethoxybenzaldehyde (3b) General procedure: To a solution of the product from step 1 (1.00 g, 5.5 mmol) and allyl bromide (0.71 mL, 8.2 mmol) in acetone (10 mL) was added K2CO3 (1.51 g, 11.0 mmol). The mixture was heated to 50°C until the starting material was completely consumed, cooled to ambient temperature and hydrolysed by addition of a semisaturated aqueous solution of NaCl (20 mL). Ethyl acetate (10 mL) was added, the organic layer was separated and the aqueous layer was extracted twice with ethyl acetate (20 mL each). The combined organic extracts were dried with MgSO4, filtered and evaporated. The residue was purified by chromatography on silica, using hexane-MTBE mixtures of increasing polarity as eluent, to furnish the title compound 3b (0.93 g, 4.2 mmol, 76%).
98% With potassium phosphate In acetone for 3h; Heating;
94% With potassium carbonate
90% With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;
90% With potassium carbonate In acetone for 40h; Heating;
44% With potassium carbonate In N,N-dimethyl-formamide for 23h; Ambient temperature;
With potassium carbonate In acetonitrile for 15h; Heating;
With potassium carbonate In acetone at 60℃; for 16h;

  • 19
  • [ 117-99-7 ]
  • [ 3446-91-1 ]
  • 4-(2-Benzoyl-phenoxymethyl)-N,N-dimethyl-benzenesulfonamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
64% With aluminum oxide; cesium fluoride In N,N-dimethyl-formamide for 4h; Ambient temperature;
  • 20
  • [ 591-50-4 ]
  • [ 90-02-8 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
95% With tetrabutylammomium bromide; sodium hydroxide; palladium dichloride In water at 100℃; for 0.75h; Green chemistry; General procedure for the preparation of 2-hydroxyarylketones from the reaction of 2-hydroxybenzaldehydes with aryl halides General procedure: In a 50 mL round bottom flask equipped with a magnetic stirring bar, tetrabutylammonium bromide (0.5 mmol, 0.16 g) was added and heated at 100 °C to be melted. Then a mixture of PdCl2 (3 mol%, 0.0053 g), aqueous NaOH (2.0 mmol, 0.08 g of NaOH dissolved in 2 mL H2O), hydroxybenzaldehyde (1.0 mmol), and arylhalide (2.0 mmol) were added to molten tetrabutylammonium bromide. The progress of the reaction was monitored by TLC. After the appropriate reaction time, the mixture was cooled to room temperature and extracted with diethyl ether (3 × 5 mL). The organic layer was isolated and dried over anhydrous Na2SO4 and purified by column chromatography over silica gel using n-hexane/ethyl acetate as eluent to afford the highly pure desired products (Table 2).
94% With nickel(II) chloride hexahydrate; tetrabutylammomium bromide; sodium hydroxide In ethylene glycol at 120℃; for 2h;
93% With 1,4-diaza-bicyclo[2.2.2]octane; palladium dichloride In water at 100℃; for 5h;
87% With dicarbonylacetylacetonato rhodium (I); sodium hydrogencarbonate In N,N-dimethyl-formamide at 100℃; for 0.5h; Schlenk technique; Inert atmosphere;
83% With palladium diacetate; potassium carbonate; catacxium A In N,N-dimethyl-formamide at 120℃; for 12h; Schlenk technique; Inert atmosphere; General procedure for the synthesis of xanthone General procedure: To an oven-dried 25 mL Schlenk tube containing a stirring bar was added 4.5 mg Pd(OAc)2 (0.02 mmol), 15.7mg nBuPAd2 (0.44 mmol), 2-bromofluorobenzene (0.50 mmol), salicylaldehyde (0.50 mmol), potassium carbonate (1.0 mmol). The Schlenk tube was vacuumed and then purged with argon before DMF (2.0 mL) was injected using a syringe. Afterwards the Schlenk tube in the ice bath was degassed by evacuation and back fillingwith argon three times. The reaction mixture was then stirred for 12 h at 120 °C. After the reaction was complete,the reaction mixture was diluted with water (5 mL), extracted with ethyl acetate (3 x 10 mL) and dried withanhydrous Na2SO4. After filtration and addition of silica gel into the solution, the organic solvent was reduced evaporated. The crude product was purified by column chromatography using ethyl acetate/n-pentane.
96 % Chromat. With N-benzyl-N,N,N-triethylammonium chloride; sodium carbonate; palladium dichloride In N,N-dimethyl-formamide at 100℃; for 4h;

  • 21
  • [ 89-95-2 ]
  • [ 1483-73-4 ]
  • [ 117-99-7 ]
  • 22
  • [ 89-95-2 ]
  • [ 71-43-2 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
84% Stage #1: benzene With polymer-supported phenyliodine(III) diacetate; sulfuric acid In acetic acid at 20℃; for 60h; Stage #2: 2-methyl-benzyl alcohol With sodium carbonate In N,N-dimethyl-formamide at 60 - 70℃; for 4h;
  • 23
  • [ 54187-96-1 ]
  • [ 117-99-7 ]
  • [ 360782-05-4 ]
YieldReaction ConditionsOperation in experiment
97% Stage #1: 2-Hydroxybenzophenone With sodium hydroxide In ethanol at 20℃; for 5h; Stage #2: 1-(chloromethyl)-1H-benzotriazole In N,N-dimethyl-formamide at 70℃; for 12h; Further stages.;
  • 24
  • [ 117-99-7 ]
  • [ 111098-56-7 ]
  • [ 360782-06-5 ]
YieldReaction ConditionsOperation in experiment
87% Stage #1: 2-Hydroxybenzophenone With sodium hydroxide In ethanol at 20℃; for 5h; Stage #2: 1-(benzotriazol-1-yl)-1-chloroethane In N,N-dimethyl-formamide at 70℃; for 12h; Further stages.;
  • 25
  • [ 117-99-7 ]
  • [ 111098-59-0 ]
  • [2-(1-benzotriazol-1-ylbutoxy)phenyl](phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% Stage #1: 2-Hydroxybenzophenone With sodium hydroxide In ethanol at 20℃; for 5h; Stage #2: 1-(benzotriazol-1-yl)-1-chloro-2-methylpropane In N,N-dimethyl-formamide at 70℃; for 12h; Further stages.;
  • 26
  • [ 117-99-7 ]
  • [ 54758-71-3 ]
YieldReaction ConditionsOperation in experiment
100% With ammonia In methanol at 20℃; for 16h; Cooling with ice;
96% With ammonia In methanol at 20℃; Sealed tube;
70% With 1,1,1,3,3,3-hexamethyl-disilazane; scandium tris(trifluoromethanesulfonate) In chlorobenzene at 90℃; for 2h; Inert atmosphere;
70% With ammonia In methanol Inert atmosphere;
50% With piperidine; ammonium iodide at 35℃; for 40h;
With ammonium iodide; calcium sulfate; triethylamine In acetonitrile at 20℃; for 44.5h;
With ammonia In methanol at 20℃; for 2h; Inert atmosphere;
With ammonia In methanol at 20℃;
11 %Spectr. With Ru(OCOCH3)2{(S)-2,2'-bis(diphenylphosphino)-1,1'-dinaphthyl)}; ammonium acetate; hydrogen In methanol at 80℃; for 24h; Autoclave;

Reference: [1]Nguyen, Thanh Binh; Wang, Qian; Gueritte, Franioise [Chemistry - A European Journal, 2011, vol. 17, # 35, p. 9576 - 9580]
[2]Choubane, Houcine; Garrido-Castro, Alberto F.; Alvarado, Cuauhtemoc; Martín-Somer, Ana; Guerrero-Corella, Andrea; Daaou, Mortada; Díaz-Tendero, Sergio; Carmen Maestro; Fraile, Alberto; Alemán, José [Chemical Communications, 2018, vol. 54, # 27, p. 3399 - 3402]
[3]Hirazawa, Yoshinobu; Kadota, Tetsuya; Kondo, Yuta; Morimoto, Hiroyuki; Morisaki, Kazuhiro; Ohshima, Takashi [Organic Letters, 2020, vol. 22, # 1, p. 120 - 125]
[4]Clarkson, Guy J.; Wills, Martin; Zheng, Ye [Organic Letters, 2020]
[5]Location in patent: scheme or table Crecente-Campo, Jose; Vazquez-Tato, M. Pilar; Seijas, Julio A. [European Journal of Organic Chemistry, 2010, # 21, p. 4130 - 4135]
[6]Mizufune, Hideya; Irie, Hiroyuki; Katsube, Susumu; Okada, Tadataka; Mizuno, Yukio; Arita, Miichiro [Tetrahedron, 2001, vol. 57, # 35, p. 7501 - 7506]
[7]Chen, Cheng-Yi; Andreani, Teresa; Li, Hongmei [Organic Letters, 2011, vol. 13, # 23, p. 6300 - 6303]
[8]Guerrero-Corella, Andrea; Esteban, Francisco; Iniesta, Manuel; Martín-Somer, Ana; Parra, Mario; Díaz-Tendero, Sergio; Fraile, Alberto; Alemán, Jose [Angewandte Chemie - International Edition, 2018, vol. 57, # 19, p. 5350 - 5354][Angew. Chem., 2018, vol. 130, # 19, p. 5448 - 5452,5]
[9]Hu, Le' an; Zhang, Yao; Zhang, Qing-Wen; Yin, Qin; Zhang, Xumu [Angewandte Chemie - International Edition, 2020, vol. 59, # 13, p. 5321 - 5325][Angew. Chem., 2020, vol. 132, p. 5359 - 5363]
  • 27
  • [ 35654-56-9 ]
  • [ 117-99-7 ]
  • {2-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}(phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With dmap In 1,2-dichloro-benzene at 160℃; for 4h;
5% at 170℃; for 0.333333h;
Stage #1: 6,7-dimethoxy-4-chloroquinoline; 2-Hydroxybenzophenone With dmap In 1,2-dichloro-benzene at 160℃; for 4h; Stage #2: With potassium hydroxide In chloroform; water Compound 62: {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-phenyl}(phenyl)-methanone Compound 62: {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-phenyl}(phenyl)-methanone; 4-Chloro-6,7-dimethoxyquinoline (58 mg), 2-hydroxybenzophenone (271 mg), and 4-dimethylaminopyridine (166 mg) were suspended in o-dichlorobenzene (5 ml), and the suspension was stirred at 160°C for 4 hr. The reaction solution was cooled to room temperature, and the solvent was then removed therefrom by distillation under the reduced pressure. Chloroform was added to the residue, and the mixture was washed with a 1 N aqueous potassium hydroxide solution and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform and by thin layer chromatography using acetone-hexane to quantitatively give 110.4 mg of the title compound. 1H-NMR (CDCl3, 400 MHz): δ 3.82 (s, 3H), 3.99 (s, 3H), 6.43 (d, J = 5.1 Hz, 1H), 6.93 (s, 1H), 7.26 (d, J = 8.3 Hz, 1H), 7.28 - 7.34 (m, 3H), 7.39 - 7.48 (m, 2H), 7.59 - 7.72 (m, 4H), 8.44 (d, J = 5.4 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 386 (M+1)+
  • 28
  • [ 40473-50-5 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
75% With air; Mn3O4 nanoparticles In N,N-dimethyl-formamide at 80℃; for 6h;
60% With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In ethyl acetate at 80℃; for 6h; 4. Synthesis of Six-membered Cyclic Sulfonamides General procedure: IBX (6.0 mmol) was added to a solution of 6a-j (5.0 mmol) in EA (10 mL) at 80 oC. The resulting suspension was stirred for 6 h and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel to afford 2-hydroxybenzophenone derivatives as a yellow solid in 60% yield.
59% With oxygen; pyrographite In xylene at 120℃; for 12h;
With manganese(IV) oxide In benzene

  • 29
  • [ 117-99-7 ]
  • [ 7462-74-0 ]
  • 2-(2-benzoyl-phenoxy)-2-methyl-propionamide [ No CAS ]
  • 33
  • [ 117-99-7 ]
  • (-)-1-<(1R)-1-hydroxyphenylmethyl>-2-hydroxybenzene [ No CAS ]
  • (+)-1-<(1S)-1-hydroxyphenylmethyl>-2-hydroxybenzene [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium phosphate buffer; D-glucose; ketoreductase enzyme 111 In tetrahydrofuran; water at 30℃; for 24h; Title compound not separated from byproducts;
77 % ee With formic acid; Ms-DENEB; triethylamine at 40℃; for 13h; Inert atmosphere; Overall yield = 94 %; Overall yield = 0.188 g; enantioselective reaction;
80 % ee With formic acid; C30H32N2O2RuS; triethylamine for 72h; Inert atmosphere; Overall yield = 80.7 percent; Overall yield = 32.6 mg;
  • 34
  • [ 117-99-7 ]
  • [ 96-32-2 ]
  • [ 938443-85-7 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; sodium iodide In acetonitrile at 90℃; for 18h; 49 Intermediate 49: (2-Benzoylphenoxy)acetic acid Methyl bromoacetate (3.0ml) was added to a suspension containing 2-hydroxybenzophenone (2.3g), potassium carbonate (3.2g) and sodium iodide (2.33g) in acetonitrile (35ml).. The mixture was stirred for 18h at 90°C under a nitrogen atmosphere and was then allowed to cool to 20°C. It was then partitioned between ethyl acetate (80ml) and water (60ml) and the organic extract washed with water (2 x 60ml) and brine (60ml), dried over magnesium sulphate and evaporated in vacuo.. The crude material was purified by flash column chromatography on silica gel eluding with ethyl acetate/petroleum ether (1:1) to give a pale yellow oil (3.05g).. This was dissolved in methanol (100ml) and 1M sodium hydroxide (35ml) and the solution was stirred for 18h at 20°C. The solution was acidified to PH 1 with 2M hydrochloric acid and extracted with ethyl acetate (2 x 80ml).. The combined organic extracts were washed with water (2 x 70ml), dried over magnesium sulphate and evaporatedin vacuo.. The crude product was purified by flash column chromatography on silica gel eluding with a gradient of ethyl acetate/petroleum ether (1:1) to ethyl acetate/methanol (4:1) to give the title compound as a pale yellow gum (1.62g, 57%). LCMS: Rt 3.41 min; m/z 257 (MH+).
  • 35
  • [ 278597-94-7 ]
  • [ 117-99-7 ]
  • [ 1026284-86-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; sodium iodide In DMF (N,N-dimethyl-formamide) at 20℃; for 18h; 1 Example 1: (2S)-2-[((2S)-2-[2-(2-Benzoylphenoxy)acetyl]amino}-4-methyl pentanoyl)amino]-3-{4-[({4-[(2-phenylacetyl)amino]-1-piperidinyl}carbonyl)oxy]phenyl}propanoic acid To a solution of 2-hydroxybenzophenone (0.134g) in anhydrous DMF (0.5ml) was added anhydrous potassium carbonate (0.093g) followed by Intermediate 28 (0.152g) and sodium iodide (0.1g).. After stirring for 18h at 20°C the mixture was partitioned between saturated aqueous sodium hydrogen carbonate (10ml) and ethyl acetate (10ml).. The layers were separated and the aqueous phase was further extracted with ethyl acetate (3 x 10ml).. The combined organic extracts were washed with water (20ml) and brine (20ml), dried over sodium sulphate and evaporated in vacuo.. The crude material was purified by flash column chromatography on silica gel eluding with dichloromethane/methanol (10:1) to give a pale yellow solid.. To a solution of this in methanol (0.5ml) was added 1M sodium hydroxide (0.22ml).. After stirring for 1.5h at 20°C the mixture was partitioned between 2M hydrochloric acid (5ml) and dichloromethane (10ml).. The layers were separated and the aqueous phase was further extracted with dichloromethane (2 x 10ml).. The combined organic extracts were washed with water (20ml) and brine (20ml), dried over sodium sulphate and evaporated in vacuo to give the title compound as a pale yellow foam (0.123g, 73%). LCMS: Rt 3.84 min;m/z 775 [M-H]-.
  • 36
  • [ 35654-56-9 ]
  • [ 117-99-7 ]
  • {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-phenyl}(phenyl)-methanone hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
10% Stage #1: 6,7-dimethoxy-4-chloroquinoline; 2-Hydroxybenzophenone at 180℃; for 1h; Stage #2: With sodium hydroxide In chloroform; water Stage #3: With hydrogenchloride In methanol Compound 63: {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-phenyl}(phenyl)-methanone hydrochloride Compound 63: {2-[(6,7-Dimethoxy-4-quinolyl)oxy]-phenyl}(phenyl)-methanone hydrochloride; 4-Chloro-6,7-dimethoxyquinoline (0.92 g) and 2-hydroxybenzophenone (1.64 g) were stirred at 180°C for one hr, and the reaction solution was cooled to room temperature. Chloroform was then added to the reaction solution, and separation was carried out with a 10% aqueous sodium hydroxide solution. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate solution and saturated brine and was dried over anhydrous magnesium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography on silica gel using hexane-acetone. Thereafter, 10% hydrochloric acid-methanol (10 ml) was added to the product, followed by concentration. The concentrate was suspended in ether. The suspension was filtered to give the title compound (174 mg, yield 10%). 1H-NMR (CDCl3, 400 MHz): δ 3.92 (s, 3H), 4.13 (s, 3H), 6.66 (d, J = 6.4 Hz, 1H), 7.15 (s, 1H), 7.35 - 7.41 (m, 3H), 7.52 - 7.61 (m, 2H), 7.67 - 7.79 (m, 4H), 8.08 (s, 1H), 8.44 (dd, J = 6.6 Hz, 6.6 Hz, 1H) Mass spectrometric value (ESI-MS, m/z): 386 (M-HCl+1)+
  • 37
  • [ 117-99-7 ]
  • [ 182499-95-2 ]
YieldReaction ConditionsOperation in experiment
44% With sodium nitrate; sulfuric acid In dichloromethane 96.a a) a) Preparation of 3-nitro-2-hydroxybenzophenone 2-Hydroxybenzophenone (3.00 g, 15.1 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.42 g, 16.7 mmol). The addition of sulfuric acid (25 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4% MeOH/CH2 Cl2) gave the desired product(1.60 g, 44%). 1 H NMR (CD3COCD3): δ 8.30 (d, 1H), 7.86 (m, 3H), 7.71 (m, 1H), 7.78 (d, 1H), 7.56 (dd 2H), 7.24 (t, 1H).
44% With sodium nitrate; sulfuric acid In dichloromethane 96 a)Preparation of 3-nitro-2-hydroxybenzophenone a)Preparation of 3-nitro-2-hydroxybenzophenone 2-Hydroxybenzophenone (3.00 g, 15.1 mmol) was dissolved in methylene chloride(40 mL) followed by the addition of sodium nitrate (1.42 g, 16.7 mmol). The addition of sulfuric acid (25 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2 Cl2) gave the desired product(1.60 g, 44%). 1 H NMR (CD3COCD3): d 8.30 (d,1H), 7.86 (m,3H), 7.71 (m, 1H), 7.78 (d, 1H), 7.56 (dd 2H), 7.24 (t, 1H).
44% With sodium nitrate; sulfuric acid In dichloromethane 96 a)Preparation of 3-nitro-2-hydroxybenzophenone a)Preparation of 3-nitro-2-hydroxybenzophenone 2-Hydroxybenzophenone (3.00 g, 15.1 mmol) was dissolved in methylene chloride (40 mL) followed by the addition of sodium nitrate (1.42 g, 16.7 mmol). The addition of sulfuric acid (25 mL/3M) was then made, followed by addition of a catalytic amount of sodium nitrite. The mixture was allowed to stir. After 24 hours, the reaction mixture was diluted with methylene chloride and extracted with water. The organic layer was dried over MgSO4 and filtered. The solvent was evaporated and chromatography of the resulting solid on silica gel (4%MeOH/CH2CH2) gave the desired product (1.60 g, 44%). 1H NMR (CD3COCD3): d 8.30 (d, 1H), 7.86 (m, 3H), 7.71 (m, 1H), 7.78 (d, 1H), 7.56 (dd 2H), 7.24 (t, 1H).
  • 38
  • (R)-α-MeHA dihydromaleate [ No CAS ]
  • [ 117-99-7 ]
  • [ 139191-80-3 ]
YieldReaction ConditionsOperation in experiment
63.7% With potassium <i>tert</i>-butylate In ethanol; isopropyl alcohol Preparation of (R)-(-)-2-[N-[1-(1H-imidazol-4-yl)-2-propyl]-(iminophenylmethyl)]phenol (No. 94) from (R)-α-MeHA dihydromaleate Preparation of (R)-(-)-2-[N-[1-(1H-imidazol-4-yl)-2-propyl]-(iminophenylmethyl)]phenol (No. 94) from (R)-α-MeHA dihydromaleate 2.24 g (20 mmol) of potassium tert-butoxide are dissolved in 30 ml of anhydrous 2-propanol. After adding 1.79 g (5 mmol) of (R)-α-MeHA dihydromaleate, the suspension obtained is stirred overnight. The material which separates off (disodium maleate) is separated by filtration and washed twice with 5 ml of anhydrous 2-propanol. The combined filtrates are evaporated to dryness and redissolved in 40 ml of anhydrous ethanol. After adding 1.19 g (6 mmol) of 2-hydroxybenzophenone, the solution is refluxed for 15 min and evaporated to dryness. Diethyl ether and a few seed crystals are added to the oil obtained and the mixture is stirred for the crystallization. The yellow material obtained is recrystallized twice from cyclohexane/anhydrous ethyl acetate. Yield 63.7% m.p.: 142°-144° C. (cyclohexane/EtOAc) C19 H19 N3 O (305.4) calculated C 74.73 H 6.27 N 13.76 found C 74.43 H 6.33 N 13.79. 1 H NMR: [D6]DMSO (300 MHz) δ=15.63 (s, replaceable by D2 O, 1H, Im-NH), 11.73 (br, replaceable by D2 O, 1H, OH), 5.51-6.54 (m, 11H, atom), 3.53 (dt, J1 =J2 =6Hz, 1H, CH--CH2), 2.73 (d, J=6Hz, 2H, CH2), 1.15 (d, J=6Hz, 3H, CH3), ppm rel. TMS, MS: EI m/z (rel.int.[%]) 305 ([M]+, 6), 224 (43), 172 (72), 171 (44), 144 (34), 118 (51), 89 (40), 69 (86), 41 (100). IR: 3076 m, 2966 m, 2600 ns, 1961 s, 1606 s, 1571 cm-1. [α]D20 =-295.4° (MeOH, c=1).
  • 39
  • [ 117-99-7 ]
  • [ 74-86-2 ]
  • [ 1005328-49-3 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: acetylene With ethylmagnesium bromide In tetrahydrofuran at 20℃; for 3.5h; Stage #2: 2-Hydroxybenzophenone In tetrahydrofuran at 0 - 20℃; for 16h; Further stages.;
  • 40
  • [ 117-99-7 ]
  • [ 88284-48-4 ]
  • [ 596-38-3 ]
YieldReaction ConditionsOperation in experiment
82% With cesium fluoride In acetonitrile at 20℃; for 12h;
  • 41
  • [ 119-61-9 ]
  • [ 117-99-7 ]
  • [ 13020-57-0 ]
  • 43
  • [ 5663-67-2 ]
  • [ 98-80-6 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
55% With oxygen; potassium carbonate; palladium(II) chloride benzonitrile complex; copper dichloride In N,N-dimethyl-formamide at 60℃; for 9h;
  • 44
  • [ 90-02-8 ]
  • [ 98-80-6 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
98% With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; copper diacetate In N,N-dimethyl-formamide at 80℃; for 8h; Sealed tube; General procedure: A mixture of salicylaldehyde (0.2 mmol) and arylboronic acid (0.4 mmol) was dissolved in DMF (2 mL) and [Cp*RhCl2]2 (4.9 mg,4 mol %) and Cu(OAc)2 (72.8 mg, 0.4 mmol) was added. Then the reaction was conducted in a sealed tube at a temperature of 80 C for 8 h. The reaction mixture was diluted with ethylacetate (20 mL),washed with H2O (310 mL). The organic layer was then dried over anhydrous Na2SO4, filtered and concentrate. The crude product was loaded on a silica gel column and flashed with 5-10% ethyl acetate in petroleum ether to afford the desired products 3 as solid or liquid
90% With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) bromide In tert-Amyl alcohol at 130℃; for 12h; Sealed tube;
85% With oxygen; sodium hydrogencarbonate; palladium(II) chloride benzonitrile complex; copper dichloride In N,N-dimethyl-formamide at 60℃; for 8h;
  • 45
  • [ 117-99-7 ]
  • [ 105-53-3 ]
  • ethyl 2-oxo-4-phenyl-2H-1-benzopyran-3-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With zirconyl chloride octahydrate; sodium amide In tetrahydrofuran at 25℃; for 0.5h; Green chemistry; General procedure for the synthesis of chromen-2-one derivatives from salicylaldehydes and active methylene compounds (3a-m) General procedure: A mixture of salicylaldehyde (1, 1 mmol), active methylene compound (2, 1.2 mmol), ZrOCl2-THF (0.048 g, 0.15 mmol) and sodium amide (0.005 g, 0.15 mmol) was stirred for 30 min at room temperature. The progress of the reaction was monitored by TLC. After the completion of reaction, the crude mixture was diluted with moist ether (20 mL). The resultant reaction mixture was washed with water (3 × 25 mL) to discharge the colour, ZrOCl2 and sodium amide. The ethereal solution obtained after extraction was dried over anhydrous Na2SO4 and evaporated under reduced pressure. Finally, this reaction mixture was purified by passing through a silica gel column chromatography to get pure product (Scheme-I).
69% With 1,8-diazabicyclo[5.4.0]undec-7-ene at 160℃; for 8h; Sealed tube;
44% With potassium <i>tert</i>-butylate at 90℃; for 0.25h; Microwave irradiation; Neat (no solvent);
  • 46
  • [ 117-99-7 ]
  • [ 56613-80-0 ]
  • [ 1309575-86-7 ]
YieldReaction ConditionsOperation in experiment
92% In ethanol for 1h; Reflux; General method for the preparation of tridentate ligands 3b and 3g General Procedure: In order to prepare the tridentate ligands 3b and 3g, equimolar quantities of the corresponding aminoalcohol and 2-hydroxybenzophenone or 2-hydroxyacetophenone, respectively, were refluxed in ethanol for 1 h. The solvent and the water formed during the reaction were eliminated to yield yellow solids which were washed with methylene chloride and used without further purification. Tridentate ligands 3a, 3c, 3d, 3e, 3f, 3h and 3i have already been published.
  • 47
  • [ 117-99-7 ]
  • [ 108-24-7 ]
  • [ 15185-05-4 ]
YieldReaction ConditionsOperation in experiment
91% With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 80℃; for 8h;
86% With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 90℃; for 8h;
86% With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 20℃; for 8h;
  • 48
  • [ 468075-00-5 ]
  • [ 117-99-7 ]
  • [ 1331753-59-3 ]
  • 49
  • [ 468075-00-5 ]
  • [ 117-99-7 ]
  • [ 1331753-36-6 ]
  • 50
  • [ 110407-59-5 ]
  • [ 117-99-7 ]
  • [ 1331753-62-8 ]
  • 51
  • [ 110407-59-5 ]
  • [ 117-99-7 ]
  • [ 1331753-39-9 ]
  • 52
  • [ 117-99-7 ]
  • [ 454-78-4 ]
  • [ 1331753-58-2 ]
  • 53
  • [ 117-99-7 ]
  • [ 454-78-4 ]
  • [ 1331753-35-5 ]
  • 54
  • [ 117-99-7 ]
  • [ 2732-80-1 ]
  • [ 1331753-60-6 ]
  • 55
  • [ 117-99-7 ]
  • [ 2732-80-1 ]
  • [ 1331753-37-7 ]
  • 56
  • [ 19434-34-5 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
51% With di(rhodium)tetracarbonyl dichloride; di-tert-butyl peroxide In chlorobenzene at 160℃; for 24h; Inert atmosphere;
  • 57
  • [ 119-61-9 ]
  • [ 117-99-7 ]
  • [ 76115-06-5 ]
  • [ 80232-65-1 ]
  • [ 632-51-9 ]
  • 58
  • [ 117-99-7 ]
  • [ 117428-49-6 ]
  • [ 1415919-85-5 ]
  • 59
  • [ 117-99-7 ]
  • [ 20439-47-8 ]
  • (1R,2R)-N,N'-bis(2-hydroxybenzophenonylidene)cyclohexane-1,2-diamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
87% In ethanol at 80℃; for 48h; Reflux; Inert atmosphere; 2.4.1 (1R,2R)-N,N′-bis(2-hydroxybenzophenonylidene)cyclohexane-1,2-diamine H2(Ph2salhex) To a solution of (1R,2R)-(-)-trans-cyclohexane-1,2-diamine (257 mg, 2.25 mmol, 1 eq) in anhydrous ethanol (8 mL) was added 2-hydroxybenzophenone (892 mg, 4.50 mmol, 2 eq). The resulting yellow solution was refluxed for 48 h at 80 °C. After cooling to ambient temperature, water (16 mL) was added whereupon a yellow precipitate was formed. The reaction mixture was stirred for 1 h and the precipitate was collected by suction filtration, washed with small portions of cold ethanol and dried in vacuo to yield a yellow powder (928 mg, 1.95 mmol, yield 87%). Mp = 86 °C; νmax(ATR)/cm-1 2929, 2856, 2160, 2029, 1977, 1604, 1571, 1492, 1442, 1300, 1253, 1147, 964, 827, 752, 719, 693, 646; δH(300 MHz; CDCl3) 1.12-1.18 (2 H, m), 1.43-1.46 (2 H, m), 1.63-1.71 (4 H, m), 3.49-3.52 (2 H, m), 6.59-6.64 (2 H, m), 6.70-6.73 (2 H, m), 6.98-7.01 (2 H, m), 7.13-7.15 (2 H, m), 7.23-7.28 (2 H, m), 7.32-7.35 (2 H, m), 7.48-7.52 (4 H, m), 7.61-7.65 (2 H, m), 15.29 (2 H, s(br)); δC(75 MHz; CDCl3) 23.7 (t, CH2), 32.4 (t, CH2), 64.7 (d, CH), 117.3 (d, CH), 117.7 (d, CH), 119.9 (s, Cq), 126.7 (d, CH), 128.1 (d, CH), 128.3 (d, CH), 128.8 (d, CH), 129.1 (d, CH), 131.8 (d, CH), 132.2 (d, CH), 133.8 (s, Cq), 162.8 (s, Cq), 173.6 (s, Cq); m/z (ESI-MS) 475 ([M+H]+. C32H30N2O2 requires 475), 497 ([M+Na]+) and 475 ([M+K]+); (HR-MS, ESI) 475.235 ([M+H]+ C32H30N2O2 requires 475.235).
With toluene-4-sulfonic acid In toluene
  • 62
  • [ 4783-68-0 ]
  • [ 611-73-4 ]
  • [ 117-99-7 ]
  • 63
  • [ 117-99-7 ]
  • [ 14708-25-9 ]
  • [Co(2-hydroxy-benzophenone-H)2(2,9-dimethyl-1,10-phenanthroline)] [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With sodium methylate In methanol; water at 20℃; for 2h; Inert atmosphere; Synthesis of [Co(bpo)2(neoc)] (3) General procedure: A solution of 1mmol 2-hydroxy-benzophenone and CH3ONa (1mmol) in MeOH (30mL), was added drop-wise to a solution of [Co(neoc)Br2] (0.5mmol) in H2O (20mL) at room temperature, according to the reaction: The solution was stirred for 2h and then turned darker and an orange-brownish solid was formed. The solid was filtered, washed with water and dried in vacuo (mean yield 62%). All compounds were prepared in inert, under argon, conditions and well degassed solutions have been used.
  • 64
  • [ 117-99-7 ]
  • [ 14708-25-9 ]
  • [ 1429189-80-9 ]
YieldReaction ConditionsOperation in experiment
50% With sodium methylate In methanol; water at 20℃; for 2h; Inert atmosphere; Synthesis of [Co(bpo)(neoc)Br] (8) General procedure: A solution of 0.5mmol 2-hydroxy-benzophenone and CH3ONa (0.5mmol) in MeOH (20mL), was added drop-wise to a solution of [Co(neoc)Br2] (0.5mmol) in H2O (20mL) at room temperature, according to the reaction: The solution was stirred for 2 h and then turned darker and a dark-greenish solid was formed. The solid was filtered, washed with water and dried in vacuum (mean yield 56%). All compounds were prepared in inert, under argon, conditions and well degassed solutions have been used.
  • 65
  • [ 117-99-7 ]
  • [ 100-51-6 ]
  • [ 33719-60-7 ]
YieldReaction ConditionsOperation in experiment
72% With tert.-butylhydroperoxide; copper diacetate In water; dimethyl sulfoxide at 80℃; for 20h; Sealed tube; 6 Typical procedure for the esterification of 2-carbonyl substituted phenols General procedure: To an oven-dried sealed tube charged with 2-hydroxyacetophenone (1a) (40.8mg, 0.3mmol, 1.0equiv), Cu(OAc)2 (2.7mg, 0.015mmol, 5mol%), and TBHP (70% in water) (0.16mL, 1.2mmol, 4.0equiv) in DMSO (1mL, 0.3M) was added benzyl alcohol (2a) (65.4mg, 0.6mmol, 2equiv). The reaction mixture was allowed to stir at 80°C for 20h. After cooling at room temperature, the reaction mixture was evaporated onto silica gel. Purification of the product by column chromatography (SiO2: n-hexanes/EtOAc=40:1) provided 3a (50.5mg) in 70% yield 4.2.6 2-Benzoylphenyl benzoate (3f) Light yellow oil; Rf=0.55 (n-hexanes/EtOAc=6:1); 1H NMR (700 MHz, CDCl3) δ 7.81 (d, J=8.3 Hz, 2H), 7.77 (d, J=8.3 Hz, 2H), 7.60-7.57 (m, 2H), 7.49 (t, J=7.4 Hz, 1H), 7.44 (t, J=7.4 Hz, 1H), 7.37-7.31 (m, 6H); 13C NMR (175 MHz, CDCl3) δ 194.7, 164.5, 148.7, 137.4, 133.4, 132.8, 132.1, 131.7, 130.3, 129.9, 129.6, 128.7, 128.3, 128.2, 125.7, 123.2; IR (KBr) ν 2917, 1738, 1666, 1600, 1449, 1293, 1262, 1202, 1104, 1059, 1023, 928 cm-1; HRMS (EI) Calcd for C20H14O3 [M]+ 302.0943, found 302.0940.
  • 67
  • [ 117-99-7 ]
  • [ 79-07-2 ]
  • [ 35351-02-1 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate In N,N-dimethyl-formamide at 80 - 145℃; for 1h; Microwave irradiation; General Procedure for the Synthesis ofBenzofuran-2-carboxamides 1-20 General procedure: The mixture of phenol (3 mmol), corresponding2-chloroacetamide (3.6 mmol), Cs2CO3 (7.5 mmol) in DMF (7mL) was placed into microwave oven (KMIC-1.5KW) and irradiated at 80 oCfor 30 min followed at 145 oC for 30 min. After the reaction mixturewas cooled to room temperature, the solvent of DMF was evaporated under reducedpressure and the residue was directly absorbed into silica gel to be purifiedby flash chromatography with CombiFlash automatic.
  • 68
  • [ 117-99-7 ]
  • [ 5221-37-4 ]
  • [ 1594133-86-4 ]
YieldReaction ConditionsOperation in experiment
40% With caesium carbonate; In N,N-dimethyl-formamide; at 80 - 145℃; for 1h;Microwave irradiation; General procedure: The mixture of phenol (3 mmol), corresponding2-chloroacetamide (3.6 mmol), Cs2CO3 (7.5 mmol) in DMF (7mL) was placed into microwave oven (KMIC-1.5KW) and irradiated at 80 oCfor 30 min followed at 145 oC for 30 min. After the reaction mixturewas cooled to room temperature, the solvent of DMF was evaporated under reducedpressure and the residue was directly absorbed into silica gel to be purifiedby flash chromatography with CombiFlash automatic.
  • 69
  • zinc(II) nitrate hexahydrate [ No CAS ]
  • [ 117-99-7 ]
  • [ 1584141-27-4 ]
YieldReaction ConditionsOperation in experiment
65% With sodium methylate In methanol at 20℃; for 2h; Synthesis of [Zn(keto)2(H2O)2] (1 and 5) General procedure: Complexes 1 and 5 were synthesized according to our published procedure[44], by the addition of a methanolic solution (15 mL) of ketoH(1 mmol), deprotonated with CH3ONa (1 mmol, 54 mg), to a methanolicsolution (10 mL) of Zn(NO3)2·6H2O (0.5 mmol, 148.75 mg) at roomtemperature. The reaction mixture was stirred for 2 h and then turnedinto yellowish. The solution was filtered and left for slow evaporation.After a few days a pale yellow microcrystalline product was collectedwith filtration, washed with cold water and air-dried
  • 70
  • [ 117-99-7 ]
  • [ 1560-56-1 ]
  • [ 39477-89-9 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: (methyl-d3)triphenylphosphonium iodide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 2-Hydroxybenzophenone In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere;
65% Stage #1: 2-Hydroxybenzophenone With n-butyllithium In tetrahydrofuran at 0℃; Inert atmosphere; Stage #2: (methyl-d3)triphenylphosphonium iodide With n-butyllithium In tetrahydrofuran at 20℃; Inert atmosphere;
  • 71
  • [ 117-99-7 ]
  • [ 1779-49-3 ]
  • [ 39477-86-6 ]
YieldReaction ConditionsOperation in experiment
91% Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 2-Hydroxybenzophenone In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere;
90% Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 2-Hydroxybenzophenone In tetrahydrofuran at 0 - 20℃; for 72h; Inert atmosphere;
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; for 2h; Stage #2: 2-Hydroxybenzophenone In tetrahydrofuran at -78 - 20℃;
Stage #1: Methyltriphenylphosphonium bromide With potassium <i>tert</i>-butylate In tetrahydrofuran at 20℃; Stage #2: 2-Hydroxybenzophenone In tetrahydrofuran at 20℃; for 6h;
Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere; Schlenk technique; Stage #2: 2-Hydroxybenzophenone In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Schlenk technique;
Stage #1: Methyltriphenylphosphonium bromide With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 2-Hydroxybenzophenone at 0 - 20℃; for 72h; Inert atmosphere;

  • 72
  • [ 533-58-4 ]
  • [ 199620-15-0 ]
  • [ 98-80-6 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
54% With C35H20F34NO3(1-)*Pd(2+)*Cl(1-); N-ethyl-N,N-diisopropylamine In water at 140℃; for 0.333333h; Microwave irradiation; 10 Carbonylative Suzuki-Miyaura coupling of aryl halideand arylboronic acid: general procedure General procedure: A mixture of the aryl halide (0.6 mmol), arylboronic acid (2.5 equiv), Mo(CO)6 (1.5 equiv), DIPEA (3.0 equiv), palladacycle 1 (1 mol % Pd), and water (1.0 mL) was heated in a pressure tube at 140 °C under microwave irradiation. The reaction was monitored by TLC. When the reaction has completed, the reaction mixturewas cooled to room temperature, poured into EtOAc (20 mL) and washed successively with water (310 mL). The organic layer was dried over anhydrous MgSO4, filtered and concentrated. The crude product was then purified by column chromatography to give pure 4.
  • 73
  • [ 108-86-1 ]
  • [ 90-02-8 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
90% With dicarbonylacetylacetonato rhodium (I); sodium hydrogencarbonate In N,N-dimethyl-formamide at 120℃; for 12h; Schlenk technique; Inert atmosphere;
85% With 1,4-diaza-bicyclo[2.2.2]octane; palladium dichloride In water at 100℃; for 29h;
81% With tetrabutylammomium bromide; sodium hydroxide; palladium dichloride In water at 100℃; for 6h; Green chemistry; General procedure for the preparation of 2-hydroxyarylketones from the reaction of 2-hydroxybenzaldehydes with aryl halides General procedure: In a 50 mL round bottom flask equipped with a magnetic stirring bar, tetrabutylammonium bromide (0.5 mmol, 0.16 g) was added and heated at 100 °C to be melted. Then a mixture of PdCl2 (3 mol%, 0.0053 g), aqueous NaOH (2.0 mmol, 0.08 g of NaOH dissolved in 2 mL H2O), hydroxybenzaldehyde (1.0 mmol), and arylhalide (2.0 mmol) were added to molten tetrabutylammonium bromide. The progress of the reaction was monitored by TLC. After the appropriate reaction time, the mixture was cooled to room temperature and extracted with diethyl ether (3 × 5 mL). The organic layer was isolated and dried over anhydrous Na2SO4 and purified by column chromatography over silica gel using n-hexane/ethyl acetate as eluent to afford the highly pure desired products (Table 2).
74% With palladium diacetate; potassium carbonate; catacxium A In N,N-dimethyl-formamide at 120℃; for 12h; Schlenk technique; Inert atmosphere; General procedure for the synthesis of xanthone General procedure: To an oven-dried 25 mL Schlenk tube containing a stirring bar was added 4.5 mg Pd(OAc)2 (0.02 mmol), 15.7mg nBuPAd2 (0.44 mmol), 2-bromofluorobenzene (0.50 mmol), salicylaldehyde (0.50 mmol), potassium carbonate (1.0 mmol). The Schlenk tube was vacuumed and then purged with argon before DMF (2.0 mL) was injected using a syringe. Afterwards the Schlenk tube in the ice bath was degassed by evacuation and back fillingwith argon three times. The reaction mixture was then stirred for 12 h at 120 °C. After the reaction was complete,the reaction mixture was diluted with water (5 mL), extracted with ethyl acetate (3 x 10 mL) and dried withanhydrous Na2SO4. After filtration and addition of silica gel into the solution, the organic solvent was reduced evaporated. The crude product was purified by column chromatography using ethyl acetate/n-pentane.

  • 74
  • [ 117-99-7 ]
  • [ 104-03-0 ]
  • 3-(4-nitrophenyl)-4-phenyl-coumarin [ No CAS ]
YieldReaction ConditionsOperation in experiment
56% Stage #1: 2-Hydroxybenzophenone; 4-nitrobenzeneacetic acid With acetic anhydride; triethylamine at 90℃; Stage #2: In diethyl ether at 20℃; 5 2.1.2.5
3-(4-Nitrophenyl)-4-phenyl-coumarin (9e) General procedure: To a mixture of 2-hydroxybenzaldehyde (7a) [or 2-hydroxyacetophenone(7b), 2,3,4-trihydroxy benzaldehyde (7c), 2-hydroxy-4-methoxybenzophenone (7d) or 2-hydroxy- benzophenone (7e)] (7.4 mmol) and 4-nitrophenylacetic acid (8) (8 mmol) in aceticanhydride (3 ml) was added triethylamine (99%, 1 ml). The reactionmixture was then refluxed overnight at 90 C, allowed to coolto r.t. and 10 ml of ether was added with occasional stirring foranother 2-3 h to afford the desired product as a precipitate thatwas collected using vacuum filtration.
  • 75
  • [ 117-99-7 ]
  • [ 117928-94-6 ]
  • C31H39N5O7 [ No CAS ]
YieldReaction ConditionsOperation in experiment
32% With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 48.0h; To a stirred solution of <strong>[117928-94-6]GLYX-13</strong> (110 mg, 0.26 mmol) in DMF (4 mL), diisopropyl ethyl amine (DIPEA) (100 tL) and 2-hydroxybenzophenone (105 mg, 0.53 mmol)were added and stirred at room temperature for 48 h. After completion of the reaction the volatiles were evaporated under reduced pressure to furnish the crude product which was purified by preparative HPLC to furnish NRX-7001 (50 mg, 32 %).j00176j 1H NMR: (4OOMHz CDC13): oe 7.71 (d, 1H), 7.51 (d, 4H), 7.28-7.18 (m, 6H), 6.98 (d, 1H), 6.82 (d, 1H), 6.76(d, 1H), 6.66-6.61 (m, 1H), 5.90 (d, 1H), 4.58 (t, 2H), 4.44 (t,4H), 4.37-4.30 (m, 2H), 4.09 (q, 2H), 3.92 (m, 1H), 3.82-3.54 (m, 5H), 3.50-3.41 (m, 2H),2.85-2.8 1 (m, 1H), 1.62 (m, 5H), 1.39-1.22 (m, 6H).j00177j Mass mlz: 594.3 [M+1].
  • 76
  • [ 117-99-7 ]
  • [ 7328-91-8 ]
  • [ 222558-57-8 ]
YieldReaction ConditionsOperation in experiment
74.5% In methanol for 5h; Reflux; 2.2.1. Preparation of 2,2′-((2,2-dimethylpropane-1,3-diyl)bis((nitrilo)(phenylmethylidyne)))-diphenol (SchB) The Schiff base (scheme 1) was synthesized according to the method described in previous papers [12]. A solution of 10 mmol 2-hydroxybenzophenone and 5 mmol 2,2-dimethyl-1,3-propanediamine in 60 mL of methanol was refluxed for 5 h. The excess of the solvent (ca. 50 mL) was then evaporated. After cooling to 4 °C, a yellow solid was produced. The polycrystalline product was collected by filtration, washed with methanol, and dried (74.5% yields). Elemental analysis of C31H30N2O2, Calcd (%): C,80.49; H, 6.54; N, 6.06. Found: C, 80.41; H, 6.63; N, 5.98.
74.5% In methanol at 65℃; for 2h; Preparation of Schiff bases General procedure: The Schiff base ligands were synthesized (Scheme 1) using a similar method described in previous papers [1, 25-27]. Mixtures of 10 mmol of appropriate ketone and 5 mmol of diamine in 40 mL of methanol were refluxed for 2 h. The excess of the solvent (ca. 30 mL) was then evaporated. After cooling to 4 C, yellow solids were formed. The products were collected by filtration, washed with cold methanol and dried in air.
  • 77
  • [ 117-99-7 ]
  • [ 279669-06-6 ]
  • C27H27O5P [ No CAS ]
  • C27H27O5P [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 75% 2: 15% With iron(III) chloride In nitromethane at 80℃; for 6h; regioselective reaction; General procedure for the allylation of arenes with phosphonoallylic alcohol 1 General procedure: To phosphonoallylic alcohol 1 (0.282 g, 1 mmol) and FeCl3 (0.016 g, 0.1 mmol) in nitromethane (3 mL) was added 4-methoxyphenol (0.620 g, 5 mmol). The mixture was stirred at 80C for 6 h. After the starting material 1 was consumed completely, solvent was removed under vacuum. Crude product was purified by column chromatography using silica gel with ethyl acetate/ hexane (1:1) mixture as the eluent.
  • 78
  • [ 117-99-7 ]
  • [ 1099-45-2 ]
  • [ 15185-05-4 ]
YieldReaction ConditionsOperation in experiment
91% With dmap In toluene for 10h; Reflux; Inert atmosphere; A mixture of 3a (20 mg, 0.1 mmol) was dissolved in toluene (2 mL), ethyl-2-(triphenylphosphoranylidene)acetate (37 mg, 0.107 mmol) DMAP (0.7 mg, 5.4% mmol) was added. Then the reaction mixture was heated at reflux under Argon for 10 h. The resulting reaction mixture was loaded on a silica gel column and flashed with 10% ethyl acetate in petroleum ether to afford the desired products 4 as solid.
  • 79
  • [ 117-99-7 ]
  • [ 96-32-2 ]
  • [ 938443-86-8 ]
YieldReaction ConditionsOperation in experiment
43% Stage #1: 2-Hydroxybenzophenone; bromoacetic acid methyl ester With potassium carbonate In acetone for 2h; Reflux; Stage #2: With sodium methylate In methanol at 60℃; for 10h; A mixture of 3a (100 mg, 0.5 mmol) was dissolved in acetone (10 mL), K2CO3 (104 mg, 0.75 mmol) and methyl bromoacetate (91.8 mg, 56.7 mL,0.6 mmol) was then added. The reaction mixture was heated under reflux for 2 h. The reaction mixture was then diluted with ethyl acetate(20 ml), washed with H2O (310 mL). The organic layer was then dried over anhydrous Na2SO4, filtered and concentrated to afford the crude product.The crude product was dissolved in MeOH (5 mL), sodium methanolate (81 mg, 1.5 mmol) was added. Then the reaction mixture was stirred for 10 h at 60 C. The reaction mixture was diluted with ethyl acetate (20 ml), washed with H2O (310 mL). The organic layer was then dried over anhydrous Na2SO4, filtered and concentrate. The crude product was loaded on a silica gel column and flashed with 10% ethyl acetate in petroleum ether to afford the desired products 5 as solid.
  • 80
  • [ 1162692-71-8 ]
  • [ 117-99-7 ]
YieldReaction ConditionsOperation in experiment
88% With copper(II) bis(trifluoromethanesulfonate); silver(l) oxide In water at 100℃; for 8h; Representative procedure for the synthesis of benzoylated naphthol derivatives General procedure: In a 10 mL reaction vial, aminonaphthol 1a (30 mg, 0.1 mmol), silver oxide (11.59 mg, 0.05 mmol), copper triflate (1.81 mg, 0.005 mmol) were taken in water (1.5 mL) and the reaction vial was closed with a crimper cap. The vial was heated in an oil bath at 100 °C. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate (3 × 10 mL). The combined organic extracts were dried over anhydrous sodium sulphate, filtered and the organic solvents were evaporated under reduced pressure to afford the crude residue. The crude residue was purified by column chromatography using silica gel (100-200 mesh) with hexane and ethyl acetate as eluent (9:1) to afford the pure product. The same procedure was followed for the synthesis of benzoylated phenol derivatives.
80% With tert.-butylhydroperoxide; water; sodium dodecyl-sulfate; copper(II) acetate monohydrate at 120℃; for 3h;
  • 81
  • [ 119-61-9 ]
  • [ 117-99-7 ]
  • [ 13020-57-0 ]
  • [ 1137-42-4 ]
  • 82
  • [ 117-99-7 ]
  • [ 780038-05-3 ]
YieldReaction ConditionsOperation in experiment
65% Stage #1: 2-Hydroxybenzophenone With ammonia In methanol at 20℃; for 20h; Stage #2: With sodium tetrahydroborate In methanol at 20℃; for 42h; 4.2. Synthesis of rac-2-[amino(phenyl)methyl]phenol (rac-1c) 2c (5.00 g, 25.2 mmol) was dissolved in dry MeOH (300 mL) and gaseous ammonia was introduced to the solution at 0 °C. Then the solution was stirred at room temperature for 20 h. The solvent was removed under reduced pressure and the residue was dissolved in dry MeOH (200 mL). NaBH4 (7.63 g, 202 mmol) was added portionwise to the mixture at 0 °C and the mixture was stirred at room temperature for 42 h. After the reaction mixture was acidified by addition of 1N HCl aq, MeOH was removed under reduced pressure. The residual solution was basified by addition of NaHCO3 until the pH became 8-9. The resulting mixture was extracted with CHCl3 (50 mL3) and the organic phase was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (hexane/EtOAc 10:1) to give rac-1c (3.26 g,16.4 mmol, 65 %) as pale yellow solid. Mp: 101-102 °C. 1H MNR (500 MHz, CDCl3): δ 7.38-7.28 (m, 5H), 7.18-7.13 (m, 1H),6.90-6.87 (m, 1H), 6.80-6.69 (m, 2H), 5.31 (s, 1H). 13C NMR (125 MHz, CDCl3): δ 157.9, 143.2, 129.0, 128.9, 128.6, 127.8, 126.9, 126.3, 119.1, 117.4, 60.0. IR (KBr): νmax 3350, 3294, 2581, 1589, 1457, 1272, 1155, 1074, 998, 755, 695, 647, 608, 574, 526 cm-1.
With titanium(IV) isopropylate; bis(acetato){2,2'-bis(diphenylphosphino)-1,1'-binaphthyl}ruthenium(II); ammonium acetate; hydrogen In methanol at 80℃; for 24h; Autoclave;
Multi-step reaction with 2 steps 1: ammonia / methanol / Inert atmosphere 2: sodium tetrahydroborate; methanol / 4 h / Inert atmosphere
  • 83
  • [ 117-99-7 ]
  • [ 60100-09-6 ]
  • N-[(2-hydroxyphenyl)(phenyl)methyl]formamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With formic acid at 120℃; for 6h; Typical Procedure for the Preparation of Formamides (2).N-[(2-Hydroxyphenyl)methyl]formamide (2a). General procedure: A mixture of 2-hydroxybenzaldehyde (2.4 g, 20 mmol),HCONH2 (11 g, 0.23 mol), and HCO2H (7.5 g, 0.16 mol) was heated at 120 °C for 6 h. After cooling to rt,the mixture was diluted with H2O (100 mL) and extracted with AcOEt (3 × 25 mL). The combinedextracts were washed with saturated aqueous NaHCO3 (4 × 20 mL) and brine (20 mL), dried (Na2SO4),and concentrated by evaporation.
  • 84
  • [ 117-99-7 ]
  • [ 616-29-5 ]
  • 2,2'-((2-hydroxypropane-1,3-diyl)bis(nitrilophenylmethylidyne))diphenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% In methanol at 65℃; for 2h; Preparation of Schiff bases General procedure: The Schiff base ligands were synthesized (Scheme 1) using a similar method described in previous papers [1, 25-27]. Mixtures of 10 mmol of appropriate ketone and 5 mmol of diamine in 40 mL of methanol were refluxed for 2 h. The excess of the solvent (ca. 30 mL) was then evaporated. After cooling to 4 C, yellow solids were formed. The products were collected by filtration, washed with cold methanol and dried in air.
  • 85
  • [ 117-99-7 ]
  • [ 239074-27-2 ]
  • C25H25NO4 [ No CAS ]
  • 86
  • [ 140-31-8 ]
  • [ 117-99-7 ]
  • 2-(phenyl((2-(piperazin-1-yl)ethyl)imino)methyl)phenol [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% In chloroform at 20℃; for 2h; 3 Synthesis of 2-(phenyl((2-(piperazin-1-yl)ethyl)imino)methyl)phenol (HL) 1.98g (10mmol) of 2-Hydroxybenzophenone dissolved in 10mL of chloroform was added into a solution of 1.29g of amino ethyl piperazine (10mmol) in 5mL of chloroform. The mixture was stirred for 2h at room temperature. After evaporation of the volatile solvent, a yellow oily compound (L) is formed. Yield: 72%. 1H NMR (400.13MHz, 298K, CDCl3): δ 15.66 (s, 1H, phenolic OH), 6.57-7.52 (m, 9H, aromatic H), 3.39-3.48 (t, 2H, aliphatic -CH2), 2.79-2.88 (m, 4H, cyclohexene -CH2), 2.60-2.68 (t, 2H, aliphatic -CH2), 2.34-2.43 (t, 4H, cyclohexene -CH2) (Fig. S1); 13C NMR (100.61MHz, 293K, DMSO): δ 174.6, 163.7, 133.9, 132.5, 131.5, 129.1, 128.8, 127.3, 119.7, 118.2, 117.2, 59.4, 54.6, 48.8, 46.0. (Fig. S2) C19H23N3O (m/z) calculated - 309.18 (M)+; obtained - 310.5 (M+H)+ (Fig. S3)
  • 87
  • [ 117-99-7 ]
  • [ 124-63-0 ]
  • 4-phenylbenzo[e][1,2]oxathiine 2,2-dioxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% Stage #1: 2-Hydroxybenzophenone With sodium hydride In N,N-dimethyl-formamide at 0 - 70℃; for 0.75h; Inert atmosphere; Stage #2: methanesulfonyl chloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #3: With hydrogenchloride; acetic acid In water for 20h; Inert atmosphere; Reflux;
  • 88
  • [ 119-61-9 ]
  • [ 117-99-7 ]
  • [ 1137-42-4 ]
YieldReaction ConditionsOperation in experiment
1: 19% 2: 10% With Co(difluoroboryl-dimethylglyoxime)<SUB>2</SUB>(CH<SUB>3</SUB>CN)<SUB>2</SUB>; water monomer; 3-cyano-1-methylquinolinium cation In acetonitrile at 20℃; for 5h; Inert atmosphere; Irradiation; Green chemistry; 30 Example 30 Using 1-methyl-3-cyanoquinoline salt as photosensitizer, Cobalt oxime complex 2 as cobalt catalyst, 5mL acetonitrile2.69 mg (1 × 10 -2 mmol) of photosensitizer and 2.80 mg (6 × 10 -3 mmol) of cobalt catalyst were charged, the atmosphere was replaced with Ar atmosphere, and then 0.2 mmol of benzophenone(R1 is COC6H5, R2, R3, R4 are independently H) and 2 mmol H2O. Room temperature, high pressure mercury lamp irradiation 5h. After completion of the reaction, H2 production was detected by GC (TCD), benzene conversion by GC (FID) was detected, and then column separation was performed. Nuclear magnetic resonance spectrometry and mass spectrometry identified products 2-hydroxybenzophenone,3-hydroxybenzophenone and 4-hydroxybenzophenone. The conversion of benzophenone was 34%, the yields of 2-hydroxybenzophenone, 3-hydroxybenzophenone and 4-hydroxybenzophenone were 19%, 4% and 10%, The yield of H2 is 34%.
With tert.-butylnitrite; water monomer; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 16h; Irradiation; Overall yield = 65 percent;
Same Skeleton Products
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