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CAS No. : | 92-83-1 | MDL No. : | MFCD00005055 |
Formula : | C13H10O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GJCOSYZMQJWQCA-UHFFFAOYSA-N |
M.W : | 182.22 | Pubchem ID : | 7107 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.08 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 55.97 |
TPSA : | 9.23 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.41 cm/s |
Log Po/w (iLOGP) : | 2.47 |
Log Po/w (XLOGP3) : | 4.23 |
Log Po/w (WLOGP) : | 3.38 |
Log Po/w (MLOGP) : | 3.22 |
Log Po/w (SILICOS-IT) : | 3.64 |
Consensus Log Po/w : | 3.39 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.27 |
Solubility : | 0.00981 mg/ml ; 0.0000538 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -4.13 |
Solubility : | 0.0134 mg/ml ; 0.0000734 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -4.93 |
Solubility : | 0.00216 mg/ml ; 0.0000119 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.35 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280 | UN#: | N/A |
Hazard Statements: | H317 | 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 |
---|---|---|
99% | With oxygen; In toluene; at 100℃; for 188h; | General procedure: Ir1 was activated by heating at 135C during 2h. Then, a mixture of benzyl alcohol (310muL, 323mg, 3mmol) and preactivated Ir1 (46mg, 1.3mol%) in toluene (1mL) was charged into a reactor tube. We purged three times (pressurizing/depressurizing cycles) with oxygen and left for 23 h at 100C under an oxygen atmosphere (balloon). Upon cooling to room temperature, the reaction mixture was filtered through celite using CH2Cl2 and dried to give the benzaldehyde (305mg, 97% yield). |
99% | With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,2-dichloro-ethane; at 20℃; for 12h;Irradiation; Schlenk technique; Sealed tube; | General procedure: A 15-mL Schlenk tube equipped with a magnetic stirrer bar was charged with <strong>[92-83-1]xanthene</strong> (1a; 182 mg, 1.0 mmol) and DDQ (2.3mg, 1 mol%). The air in the tube was replaced with O2 and the tube was sealed with a rubber plug. TBN (5.9 muL, 5 mol%), AcOH(12.0 mg, 20 mol%), and DCE (5.0 mL) were added. The Schlenktube was placed in a dark box and illuminated with a 18 W blue LED. The mixture was stirred vigorously under an O2 balloonuntil the reaction was complete (GC). The mixture was thenconcentrated on a rotary evaporator, and the residue was purifiedby column chromatography (silica gel, PE-EtOAc) to give awhite solid; yield: 194 mg (99%); mp 174-175 C.1H NMR (500 MHz, CDCl3): delta = 8.35-8.33 (m, 2 H), 7.73-7.70(m, 2 H), 7.48 (d, J = 8.5 Hz, 2 H), 7.39-7.36 (m, 2 H). 13C NMR(125 MHz, CDCl3): delta = 177.2, 156.2, 134.8, 126.7, 123.9, 121.9,118.0. MS (EI): m/z (%): 196.11 (93) [M]+, 139.10 (100). |
96% | With potassium hexafluorophosphate; iron(III) nitrate monohydrate; oxygen; In acetonitrile; at 80℃; for 2h; | To a 35 mL tube, 1 mmol of oxacanthracene (formula (1-1)), 0.1 mmol of Fe (NO3) 3 · 9H2O, 0.2 mmolOf KPF6 and 3 mL of acetonitrile, with oxygen to replace the tube air,Close the bottle with a rubber stopper, insert the oxygen balloon,The reaction flask was placed in a preheated oil bath and heated to 80 C for 2 h.Filtration, the filtrate vacuum distillation solvent, and then column chromatography separation,A mixture of ethyl acetate / petroleum ether in a volume ratio of 1:50 was used as the eluent,The eluate containing the target compound was collected and the solvent was evaporatedThe product was anoxanthrone and the isolated yield was 95%.; The reaction was carried out in the same manner as in Example 1 except that the amount of KPF6 was changed to 0.3 mmol,The yield of the xanthone was 96%. |
95% | With tert.-butylhydroperoxide; 2.9-dimethyl-1,10-phenanthroline; copper(II) choride dihydrate; In water; at 20℃; for 1h; | General procedure: A stock solution of CuCl2·2H2O in water (0.0171 g/mL) was prepared (by dissolving 0.171 g in 10 mL H2O). To a Teflon screw cap glass tube, catalyst A (100 muL of a stock solution, 0.01 mmol of CuCl2, 2.1mg, 0.01 mmol of neocuproine) was added. Then 0.7 mL of H2O, 0.2 mmol of arylalkanes, and 70 % aq tert-butyl hydroperoxide (200 muL, 1.4 mmol) were added in each case. The mixture was stirred vigorously at room temperature till to its reaction time specified in the Tables 2 and 3. The reaction mixture was then diluted with ethyl acetate and the products dissolved in ethyl acetate layer were analyzed by GC using internal standard 1,4-di-tert-butylbenzene (19.4 mg, 0.1 mol). For product separation, the aqueous phase was extracted with ethyl acetate (3×10 mL). The combined extracts were dried over anhydrous MgSO4 and filtered. The filtrate was concentrated and product isolation was carried out by TLC. The pure products of benzophenone, 9-fluorenone (Table 2, entries 2 and 3) and 4-methoxyacetophenone (Table 3 entry 2) were obtained from drying their ethyl acetate extract without chromatographic workup. Filtration of the reaction mixture afforded pure 9-xanthenone (Table 2, entry 4). |
95% | With tert.-butylhydroperoxide; 1-n-butyl-3-methylimidazolim bromide; In water; at 55℃; for 20h; | General procedure: Charged 0.5 mmol of 3-(9H-fluoren-2-yl)prop-2-yn-1-ol 13a (110 mg, 0.5 mmol), 0.5 mL of [bmim]Br and TBHP (0.5 mL, 3.6 mmol) were taken in a round bottom flask and heated to 55 C until completion of the reaction. The reaction course was monitored by TLC. After completion of the reaction, the reaction mixture was extracted using ethyl acetate (3 * 4 mL). The organic layer was concentrated under vacuum and purified by column chromatography on silica gel to afford the desired product as 2-(3-hydroxyprop-1-yn-1-yl)-9H-fluoren-9-one 13b Yellow Solid; |
93% | With dihydrogen peroxide; trifluoroacetic acid; zinc dibromide; In 1,4-dioxane; water; at 100℃; for 16h; | General procedure: In a 25 mL pressure tube, ZnBr2 (10 mol %) and a stirring bar were added. After the addition of diphenylmethane (1 mmol), trifluoroacetic acid (0.2 mL) and 1,4-dioxane (2 mL) by syringe, H2O2 (4 mmol; 30% aqueous) was added in one pot to the solution and the final solution was kept at 100 C for 16 h. Then hexadecane (100 mg) and ethyl acetate (3 mL) were injected, a part of solution was taken for GC and GC-MS analysis after properly mixed. All the products are commercially available. |
93% | With oxygen; nitric acid; In acetonitrile; at 140℃; under 760.051 Torr; for 3h; | General procedure: After an about 45 mL glass tube was charged with 2 mL acetonitrile, 0.5 mmol substrate and 0.075 mmol HNO3, the system was flushed with oxygen gas three times. Subsequently, the reaction tube was sealed and heated with magnetic stirring at 140 C for 3 h. When the reaction time was reached, the reaction mixture was cooled to room temperature. Finally, evaporation of solvent followed by column chromatography yielded the targeted product. GC yields were obtained by the GC analysisof the mixture from another parallel experiment. |
90% | With 1,2,3-Benzotriazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; dibenzoyl peroxide; In 1,2-dichloro-ethane; at 80℃; for 6h;Schlenk technique; | A 35-mL Schlenk tube, equipped with a magnetic stirring bar, was charged with 9H-<strong>[92-83-1]xanthene</strong> 1a (137 mg, 0.75 mmol), 1H-benzo[d][1,2,3]triazole 2a (60 mg, 0.5 mmol), and BPO (242 mg, 1.0 mmol), followed by the addition of DCE (5.0 mL). The mixture was stirred at 80 C for 6 h; then it was quenched with saturated aqueous Na2S2O3 (2.0 mL), saturated aqueous K2CO3 (2.0 mL), and water (20.0 mL), and extracted with CH2Cl2 (20.0 mL) three times. The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 12:1, v/v) to afford 1-(9H-xanthen-9-yl)-1H-benzo[d][1,2,3]triazole 3a as a colorless crystal (144 mg, 96% yield). |
88% | With N-hydroxyphthalimide; 6-((cobalt(II) 4,9,16,23-tetraaminephthalocyanin-4-yl))cellulose; oxygen; potassium hydroxide; In o-xylene; for 9h;Reflux; Green chemistry; | General procedure: N-Hydroxyphthalimide (0.01 g, 0.06 mmol) was added to a two-necked flask equipped with a gas bubbling tube containing colloidal of CoPcCell (0.05 g), tetraline (0.13 g, 1.00 mmol) and KOH (0.25 mmol) in o-xylene (5 mL). The mixture was stirred under reflux conditions in O2 atmosphere provided with a balloon. The reaction temperature was raised to refluxing o-xylene. The progress of the reaction was followed by TLC. Upon completion, CoPcCell was separated by filtration and washed with acetone (5 mL). Tetralone was isolated from the mixture using column chromatography with n-hexane:ethyl acetate (10:1) in 88% yield. |
87% | With oxygen; lithium hexamethyldisilazane; In tetrahydrofuran; at 60℃; under 760.051 Torr; for 12h;Sealed tube; Green chemistry; | General procedure: To an 8 mL oven-dried vial, 4-benzylpyridine (0.1 mmol), dry THF (1 mL), LiHMDS (0.15mmol) were added subsequently. The reaction system was sealed by a rubber septum with a needleconnected with O2 balloon. After stirring at 60 C for 12 h, the reaction mixture was passed througha short pad of silica gel and eluted with ethyl acetate (1 mL × 3). The combined organics wereconcentrated under reduced pressure. The residue was purified by flash chromatography to givethe diarylketone 2a as white solid (15.6 mg, 85% yield). |
83% | With tert.-butylhydroperoxide; In water; at 100℃; for 24h; | General procedure: Caution. tert-Butyl hydroperoxide is an exceptionally dangerous chemical that is highly reactive, flammable, and toxic. It is corrosive to skin and mucous membranes and causes respiratory distress when inhaled. A solution of secondary alcohol (1 mmol) and 70% TBHP (6 or 10 equiv.) was stirred at 100 C for 24 h. The reaction mixture was quenched with the saturated solution of sodium thiosulfate (5 mL) and extracted with dichloromethane (3 x 10 mL). The combined dichloromethane extracts were dried over anhydrous Na2SO4 and filtered, and then the solvent was removed under reduced pressure. The residue was purified by flash column chromatography on silica gel with PE or PE/EtOAc as the eluent to obtain the desired products. |
73% | With aluminum(III) nitrate nonahydrate; In acetonitrile; at 0 - 23℃; | General procedure: In a 25 ml dry round-bottom flask was suspended polymeric PhIO (0.25 equivalent) indry acetonitrile at 23C. Then, Al(NO 3 ) 3 (0.35 equivalent) was added and stirred for10 min, afterward, it was cooled to 0C. The benzylic aryl derivative (1 equivalent) wasincorporated in one portion. The reaction was warmed to 23C for a period of 2-4 huntil the starting material was fully consumed judging its advance by TLC. The reactionmixture was quenched by the addition of NH 4 Cl saturated solution (25 mL) and thenextracted with EtOAc (3 10 mL). The organic extracts were collected, dried overanhydrous sodium sulfate, filtered, and concentrated in vacuo to remove the solventand yield the crude of the reaction. The product was purified by flash column chroma-tography on silica gel (100-200 mesh) with EtOAc/hexane system. |
72% | With oxone; cobalt(II) perchlorate; In water; acetonitrile; at 25℃; for 3h;Sealed tube; | General procedure: A mixture of 1 (0.2 mmol), Co(ClO4)2 (0.02 mmol), Oxone (1.2 mmol), CH3CN (2 mL) and H2O (2 mL) was stirred in a sealed tube at 25 C for 3 h. After the reaction was completed (as monitored by TLC), the mixture was placed and allowed to separate into layers. Then the upper organic layer was separated, dried with anhydrous Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by preparative TLC (petroleum ether/ethyl acetate = 10:1, v/v) to yield 2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium bis(2-methoxyethoxy)aluminium dihydride; In toluene; at 23 - 60℃; for 3h;Inert atmosphere; | A 50 ml eggplant type flask was charged with a 70 mass% toluene solution of sodium dihydrobis (2-methoxyethoxy) aluminate (Registered trademark: VITRIDE (VITRIDE), manufactured by Bertrass Specialties Incorporated) 3.47 g (12 mmol) Toluene (10 ml) was added to make it under a nitrogen atmosphere, 588 mg (3 mmol) of xanthone (Wako Junyaku reagent grade 1) dissolved in 10 ml of toluene (special grade, Wako Pure Chemical Industries, Ltd.) was added and stirred at room temperature (23 C.). after that, This solution was heated to 60 C. and heated and stirred for 3 hours. After standing to cool, 10 ml of a 2N sodium hydroxide aqueous solution was added under ice cooling to make it alkaline. The organic phase was separated and the organic phase was washed twice with 10 ml of saturated sodium bicarbonate. After washing, the organic phase was dried with magnesium sulfate and then toluene was distilled off. As a result, A solid (crude xanthene) was obtained as a residue. This crude xanthene was purified by silica gel column chromatography to obtain 492 mg (90% yield) of xanthene |
80% | A 50 ml eggplant-shaped flask was placed under a nitrogen atmosphere, and 430 mg (3 mmol) of tri-n-propylamine (Wako pure chemical reagent grade 1: tertiary amine) and 588 mg (3 mmol) of xanthone (Wako Pure Chemical Reagent 1 grade) And the mixture was stirred at room temperature (23 C.). To this solution, 1219 mg (9 mmol) of trichlorosilane was slowly added dropwise using a dropping funnel.After the dropwise addition, the reaction solution was stirred at 60 C. for 2 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, slowly added with 10 ml of a 5% by mass methanol solution of potassium hydroxide and stirred at room temperature for 1 hour (hydrolysis of the silane compound: contacting the reaction mixture with a basic solution). It was confirmed that this mixed solution (reaction mixture) was basic.The resulting mixed solution (reaction mixture) was poured into a separating funnel containing 30 ml of methylene chloride (special grade Wako Pure Chemical Industries, Ltd.), 10 ml of water was added, and the component dissolved in water was extracted into the aqueous phase. After carrying out this operation twice more, the separated methylene chloride solution (organic phase) was dried over magnesium sulfate and methylene chloride was distilled off to obtain a solid (crude xanthene) as a residue. This crude xanthene was purified by silica gel column chromatography to obtain 437 mg (yield: 80%) of xanthene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With [5,10,15,20-tetrakis-1-methyl-4-pyridylporphyrinate iron(III) tetrachloride salt]chloride; 3-chloro-benzenecarboperoxoic acid In acetonitrile at 20℃; aq. acetate buffer; | |
1: 55% 2: 10% | With [MnIV(3,6,9-trimethyl-3,6,9-triaza-1(2,6)-pyridinacyclodecaphane)(OH)(OCH2CF3)]2+ In 2,2,2-trifluoroethanol; acetone at 25℃; | |
1: 51% 2: 13% | With [MnIV(N,N'-di-tert-butyl-2,11-diaza[3.3](2,6)-pyridinophane)(OIPh)(OH)]2+ In 2,2,2-trifluoroethanol; acetonitrile at 20℃; | 2.2-1 <2-1>Hydrogen Atom Abstraction (HAA) General procedure: At 20° C., in a 1 mM solution of the Example 1 complex dissolved in CH3CN/CF3CH2OH (v/v = 3:1) (red line in FIG. 4(a)), 25 mM of 9,10-dihydroandrocene ( 9,10-dihydro anthracene, DHA) was treated to confirm whether the electrophilic reaction proceeded, through the UV-Vis spectrum measurement method used in Experimental Example 1. The absorption band at 710 nm of the Example 1 composite was changed according to the first order rate reaction. The change in the UV-Vis spectrum confirmed as the reaction proceeds is shown in FIG. 4(a).As a result of analyzing the oxidation reaction product of 9,10-dihydroanthracene (DHA), it was confirmed that anthracene was produced in a yield of 84±5%. In addition, it was confirmed that the Example 1 complex was decomposed to produce [MnIII(TBDAP)(OH)(X)]+ (X = OTf- or CF3CH2O-). |
1: 4 % Turnov. 2: 74 % Turnov. | With oxygen; ozone In dichloromethane at 0℃; for 0.0666667h; var. solvents (CHCl3, CCl4), presence of singlet oxygen acceptor (1,3-diphenylisobenzofuran, tetraphenylcyclopentadiene ) at -78 deg C; | |
1: 75 %Spectr. 2: 10 %Spectr. | With Fe(4+)*O(2-)*NO3(1-)*C56H52N4(1-) In dichloromethane at -30℃; Schlenk technique; | |
1: 51 %Chromat. 2: 13 %Chromat. | With iodosylbenzene; [MnII(N,N'-di-tert-butyl-2,11-diaza[3.3](2,6)-pyridinophane)(OTf)2] In 2,2,2-trifluoroethanol; acetonitrile at 20℃; | |
With osmium(VIII)-tetroxide; tetra-n-butylammonium acetate In acetonitrile at 70℃; for 5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With air at 650 - 850℃; Formation of xenobiotics; Further byproducts given. Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 65% 2: 3.6% | at 340 - 360℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With paraformaldehyde In sulfuric acid | 90 EXAMPLE 90 EXAMPLE 90 A reaction mixture of 4-methylimidazole and paraformaldehyde in sulfuric acid is first prepared as in Example 88, and 30.6 parts of a condensate of 2 moles of 2-chloroaniline and 1 mole of 3,6-dichlorofluoran are introduced, a little at a time, at 0°-5° C., after which the mixture is stirred for 15 hours at 20°-23° C. and worked up as in Example 88. Yield: 38 parts of the xanthene dye of the formula STR52 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride; water In ethanol at 25℃; for 2h; Inert atmosphere; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With oxygen; at 40℃; under 750.075 Torr; for 24h;Sealed tube; | Oxyanthracene (1 equiv), MIL-101 (Cr) -SO3H (1 mol% -15 mol%), and cyclopentanone (5 equiv) were added successively to the reaction tube. Oxygen flow purge reaction bottle in addition to air, sealed reaction tube, inserted oxygen balloon, stirring at 40 C for 24 h. After the reaction, the solid catalyst was separated by centrifugation, and the solid was washed three times with a solvent and the solution was combined The solvent was evaporated under reduced pressure and the concentrate was separated by column chromatography (petroleum ether / ethyl acetate as eluent) to give C-C coupling product 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 78% 2: 15% | With trifluorormethanesulfonic acid; oxygen In ethyl acetate at 20℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With aluminum (III) chloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; | Bromo-1-[7-(6-bromohexanoyl)-9H-xanthen-2-yl]-hexan-1-one (2) In a two-necked flask xanthene(1, 200 mg, 1.10 mmol) and AlCl3 (190 mg, 1.41 mmol) were added to anhydrous DCM (2 mL) at 0 °C under Ar. To the solution 6-bromohexanoyl chloride (0.43 mL, 2.80 mmol) in anhydrous DCM (2 mL)was added dropwise. The reaction was then allowed to warm up to room temperature. After 5 h (TLC 30% hexane-CHCl3 6:4), the solution was neutralized at 4 °C with a saturated solution of sodium bicarbonate. The crude product was than extracted with DCM (3 × 50 mL), dried over Na2SO4 andtaken to dryness in vacuo. The crude product was purified by flash column chromatography(30 % - 60 % CHCl3 in hexane). Compound 2 was obtained as a yellow oil (509 mg, 0.95 mmol, 86 %). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | To a mixture of xanthene (1, 100 mg, 0.54 mmol), previously solubilised in dry THF (5 mL) a solution of BuLi (3 mmol) was added under Ar at room temperature. The simultaneous carbanion formation caused an immediate colour change of the solution from colourless to red. The solution was transferred dropwise to a flask containing 1,4-diidodoproane (0.15 mL, 2 mmol) in dry THF (5 mL) at -50 C. The reaction was allowed to warm to room temperature after 2 h and the reaction stirred overnight at room temperature. After approx. 14 h (TLC 40% hexane-CHCl3 7:3), the solvent was evaporated in vacuo. The crude product was dissolvedin DCM (75 mL), washed three times with water (30 mL), dried (Na2SO4) and taken to dryness in vacuo. The crude product obtained was purified by flash column chromatography (0%-40% CHCl3 in hexane). A white powder of 9 was obtained (37.7 mg, 0.25 mmol, 42%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | In tetrahydrofuran; hexane; at 0 - 20℃; for 0.2h;Inert atmosphere; | In a 25 mL flask, xanthene (1, 350 mg, 1.92 mmol),dissolved in dry THF (10 mL) and diiodopropane (0.2 mL 1.74 mmol) were stirred under argon at 0 C. n-Butyllithium (1 mL, solution 2.5 M in hexanes) was added dropwise, after which the reactionwas heated up to room temperature. After approx 2 h (TLC 40% hexane-CHCl3 7:3), solvent was evaporated in vacuo. The crude product was dissolved in DCM (75 mL), washed three times withwater (30 mL), dried over Na2SO4 and taken to dryness in vacuo. The crude product was purified byflash column chromatography (0%-40% CHCl3 in hexane), to give 12 as a white powder, (410 mg,0.93 mmol, 48% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 16h; Inert atmosphere; | |
Multi-step reaction with 2 steps 1: potassium hexamethylsilazane / 1,4-dioxane; toluene / 1.5 h / 80 °C / Inert atmosphere 2: potassium hexamethylsilazane / 1,4-dioxane; toluene / 16 h / 80 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 60% 2: 39% | With potassium hexamethylsilazane In 1,4-dioxane; toluene at 80℃; for 1.5h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With oxygen at 25℃; for 12h; Irradiation; | |
83% | With 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile at 20℃; for 12h; Molecular sieve; | 1 Example 1A method for synthesizing 9-(2,4-dimethoxyphenyl)-9H-xanthene. Take 15mL pressure resistant reaction tube,Add DDQ 45mg,Xanthene 36mg,1,3-dimethoxybenzene 83mg,Molecular sieve 100mg,2mL of acetonitrile,Open reaction,Stir at room temperature for 12 h.After the reaction was completed, 10 mL of ethyl acetate was added to quench the reaction.Wash with 10 mL of brine,Divide the organic phase,The aqueous phase was extracted 3 times with ethyl acetate.Combine the organic phase,Separation by column chromatographyPure 9-(2,4-dimethoxyphenyl)-9H-xanthene 50 mg, yield 83%,IncomeThe molecular structure of 9-(2,4-dimethoxyphenyl)-9H-xanthene is |
66% | With toluene-4-sulfonic acid In neat (no solvent) at 100℃; for 30h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With air In ethanol at 20℃; for 24h; Green chemistry; | |
87% | With air In ethanol at 20℃; for 24h; Schlenk technique; | 2 Example 2 Synthesis of 9-((4-ethylphenyl)thio)-9H-oxaindole The structure of 9-((4-ethylphenyl)thio)-9H-xanthene is as follows:The specific preparation process is as follows: 55.2 mg of p-ethylthiophenol (0.4 mmol) and 36.4 mg of xanthene (0.2 mmol) are put into 15 mL of Schlenk, 2 mL of absolute ethanol is added, and the solution is completely dissolved by magnetic stirring at room temperature, and monitored by TLC. Reaction process. After reacting at room temperature for 24 hours, the solvent ethanol was distilled off to obtain a crude product, which was then obtained by column chromatography using a petroleum ether/ethyl acetate volume ratio of 100/1 to obtain 9-((4-ethylphenyl). Thio)-9H-oxaxan, a colorless oily liquid. The yield in this step was 87% (55.3 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With air; In ethanol; at 20℃; for 24h;Schlenk technique; | The structure of 9-((4-tert-butylphenyl)thio)-9H-xanthene is as follows:The specific preparation process is as follows: 66.4 mg of p-tert-butylthiophenol (0.4 mmol) and 36.4 mg of xanthene (0.2 mmol) are put into 15 mL of Schlenk, 2 mL of absolute ethanol is added, and the solution is completely dissolved by magnetic stirring at room temperature, and passed through TLC. Monitor the progress of the reaction. After reacting at room temperature for 24 hours, the solvent ethanol was distilled off to obtain a crude product, which was then obtained by column chromatography using a petroleum ether/ethyl acetate volume ratio of 100/1 to obtain 9-((4-tert-butylphenyl). ) thio)-9H-xanthene, a colorless oily liquid. The yield in this step was 96% (66.4 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With air In ethanol at 20℃; for 24h; Green chemistry; | |
60% | With air In ethanol at 20℃; for 24h; Schlenk technique; | 9 Example 10 Synthesis of 9-((2,3-dichlorophenyl)thio)-9H-oxaindole The structure of 9-((2,3-dichlorophenyl)thio)-9H-xanthene is as follows:The specific preparation process is as follows: 71.1 mg of 2,3-dichlorothiophenol (0.4 mmol) and 36.4 mg of xanthene (0.2 mmol) are put into 15 mL of Schlenk, 2 mL of absolute ethanol is added, and the solution is fully dissolved by magnetic stirring at room temperature. TLC monitors the progress of the reaction. After reacting for 24 hours at room temperature, the solvent ethanol was distilled off to obtain a crude product, which was then obtained by column chromatography using a petroleum ether/ethyl acetate volume ratio of 100/1 to obtain 9-((2,3-dichlorobenzene). Base) thio)-9H-oxaxan, a colorless oily liquid. The yield in this step was 53% (37.9 mg). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With air In ethanol at 20℃; for 24h; Green chemistry; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With methanesulfonic acid; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 2h; Electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With dibenzoyl peroxide In 1,2-dichloro-ethane at 80℃; for 6h; Schlenk technique; | Taking the synthesis of 3a as an example: General procedure: A 35-mL Schlenk tube, equipped with a magnetic stirring bar, was charged with 9H-xanthene 1a (137 mg, 0.75 mmol), 1H-benzo[d][1,2,3]triazole 2a (60 mg, 0.5 mmol), and BPO (242 mg, 1.0 mmol), followed by the addition of DCE (5.0 mL). The mixture was stirred at 80 °C for 6 h; then it was quenched with saturated aqueous Na2S2O3 (2.0 mL), saturated aqueous K2CO3 (2.0 mL), and water (20.0 mL), and extracted with CH2Cl2 (20.0 mL) three times. The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 12:1, v/v) to afford 1-(9H-xanthen-9-yl)-1H-benzo[d][1,2,3]triazole 3a as a colorless crystal (144 mg, 96% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With dibenzoyl peroxide In 1,2-dichloro-ethane at 80℃; for 6h; Schlenk technique; | Taking the synthesis of 3a as an example: General procedure: A 35-mL Schlenk tube, equipped with a magnetic stirring bar, was charged with 9H-xanthene 1a (137 mg, 0.75 mmol), 1H-benzo[d][1,2,3]triazole 2a (60 mg, 0.5 mmol), and BPO (242 mg, 1.0 mmol), followed by the addition of DCE (5.0 mL). The mixture was stirred at 80 °C for 6 h; then it was quenched with saturated aqueous Na2S2O3 (2.0 mL), saturated aqueous K2CO3 (2.0 mL), and water (20.0 mL), and extracted with CH2Cl2 (20.0 mL) three times. The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 12:1, v/v) to afford 1-(9H-xanthen-9-yl)-1H-benzo[d][1,2,3]triazole 3a as a colorless crystal (144 mg, 96% yield). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | Stage #1: 4-methoxybenzene sulfonamide With [bis(acetoxy)iodo]benzene In dichloromethane at -20℃; for 1h; Inert atmosphere; Stage #2: xanthene With lithium bromide In dichloromethane at -20 - 20℃; for 24h; Inert atmosphere; | General procedure for the benzylic C-H amidation of xanthenes 1 and their derivatives (Scheme 4) General procedure: In a flame-dried two-necked round-bottomed flask, under nitrogen, phenyliodine(III) diacetate (PIDA,mg, 0.24 mmol, 1.2 equiv.) and 4-toluenesulfonamide (51.4 mg, 0.30 mmol, 1.5 equiv.) wereadded in dry CH2Cl2 (3 mL) at -20 oC, and the resulting solution was stirred for 1 h. Xanthene (0.2 mmol),finely powdered lithium bromide (20.8 mg, 0.24 mmol, 1.2 equiv.) and M-K10 (100 mg) were then addedand the resulting mixture was stirred at room temperature. After 24 h, saturated aqueous sodiumcarbonate was added and the resulting solution was stirred for an additional 5 min. The organic layer wasseparated, washed again with saturated aqueous sodium carbonate, then with dilute aqueous sodiumthiosulfate, and dried over anhydrous sodium sulfate. After removal of the solvents, the residue wassubjected to column chromatography on silica-gel (eluents: n-hexane/EtOAc) to give the benzylicamination product 3 in the indicated yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With indium(III) triflate In di-isopropyl ether at 95℃; for 24h; Inert atmosphere; Sealed tube; | |
85% | With titanium tetrachloride In dichloromethane at 20℃; for 24h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tert-butylammonium hexafluorophosphate(V) In methanol; acetonitrile at 20℃; for 3h; Electrochemical reaction; regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tert.-butylhydroperoxide; oxygen In tetrahydrofuran at 70℃; for 24h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With tetra-n-butylammonium tetrafluoroborate; trifluoroacetic acid In 2,2,2-trifluoroethanol at 25℃; for 8h; Electrochemical reaction; Inert atmosphere; Schlenk technique; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With tetra-n-butylammonium tetrafluoroborate; trifluoroacetic acid In 2,2,2-trifluoroethanol at 25℃; for 8h; Electrochemical reaction; Inert atmosphere; Schlenk technique; |
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