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CAS No. : | 1009-14-9 | MDL No. : | MFCD00009480 |
Formula : | C11H14O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XKGLSKVNOSHTAD-UHFFFAOYSA-N |
M.W : | 162.23 | Pubchem ID : | 66093 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 51.06 |
TPSA : | 17.07 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -4.94 cm/s |
Log Po/w (iLOGP) : | 2.39 |
Log Po/w (XLOGP3) : | 3.31 |
Log Po/w (WLOGP) : | 3.06 |
Log Po/w (MLOGP) : | 2.69 |
Log Po/w (SILICOS-IT) : | 3.21 |
Consensus Log Po/w : | 2.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.04 |
Solubility : | 0.149 mg/ml ; 0.000918 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.34 |
Solubility : | 0.0734 mg/ml ; 0.000452 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.94 |
Solubility : | 0.0188 mg/ml ; 0.000116 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.11 |
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: |
* 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 |
---|---|---|
95.8% | With hydrogen In 1,4-dioxane at 220℃; | |
78% | With hydrogen In methanol at 50℃; for 18h; chemoselective reaction; | |
77% | Stage #1: phenyl butyl ketone With iron(III) chloride In methanol at 20℃; for 0.05h; Stage #2: In methanol at 20℃; for 0.166667h; chemoselective reaction; |
With cyclohexane; copper-aluminium oxide catalyst at 150 - 180℃; Hydrogenolyse; | ||
With sodium ethanolate; hydrazine hydrate at 180℃; | ||
With hydrogenchloride; amalgamated zinc | ||
With formic acid at 300℃; beim Leiten ueber Kupfer; | ||
With hydrazine | ||
With hydrogen In ethanol at 20℃; for 48h; Irradiation; | 5. Catalytic reaction In a typical procedure, as-synthesized Pd/MoO3 catalyst (20 mg) was placed in a Pyrex schlenk flask, followed by H2 reduction under the flow of H2 (20 mL/min) at room temperature for 30 min. After the connection to a balloon (Volume = 500 mL), 10 mL of ethanol solution containing benzophenone (0.2 mmol) and n-tetradecane (0.1 mmol) was injected into the reactor through a rubber septum by using a syringe. The reaction was performed under atmospheric pressure of H2 using a balloon at room temperature (20 ± 3 °C) with magnetic stirring in the dark or under visible light irradiation (λ > 420 nm) conditions. A 500 W Hg-Xe short arc lamp (SAN-EI ELECTRIC XEF-501S) with a 420 nm cutoff filter was used to simulate visible light (λ > 420 nm, Intensity = 320 mW/cm2). At given time intervals, 500 μL of the suspension was retrieved, filtered, and analyzed by a gas chromatograph (Shimadzu GC-2010) with a frame ionization detector (FID) equipped with a capillary column (HiCap-CBP10, 25 m × 0.22 mm ID × 0.25 μmdf). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With C28H35ClCoN5(1+)*Cl(1-); potassium tert-butylate; hydrogen; In tetrahydrofuran; at 20℃; under 22502.3 Torr; for 16h;Autoclave; | General procedure: In an argon filled glove box, the cobalt catalyst (LNHC/CoCl2 or Co-2a) and the base wereweighted into a 4mL vial equipped with a magnetic stir bar, followed by addition of the solvent.After shaking of the vial for 30 seconds, the carbonyl substrate was then added. The vial wasplaced into a Parr Instruments autoclave, which was then sealed, removed from the glove boxand purged with hydrogen gas. The autoclave was heated to certain temperature. After reactionfor 16 hours, the autoclave was cooled down to 0 oC before releasing the hydrogen gas. Forquantitative GC analysis, biphenyl (1.0 mmol) as internal standard was added. The organiclayer was then filtrated and diluted for GC analysis. The stereo-selectivity of the hydrogenatedproducts of cyclohexanones were determined by NMR with mesitylene as the internal standard.The desired hydrogenation product was further isolated by flash column chromatography. |
94% | With C44H40ClN2NiP2(1+)*F6P(1-); hydrogen; potassium hydroxide; In isopropyl alcohol; at 120℃; under 30003 Torr; for 18h;Autoclave; | General procedure: Ni-based catalyst (0.01 mmol) was added into a dried autoclave (100 mL). After the addition of fresh distilled iPrOH (20 mL), the autoclave was purged with H2 (30 bar) five times. The mixture was then stirred under 30 bar H2 for 1 h. After releasing the H2 gas in a fumehood, KOH in iPrOH (1 M, 0.2 mL) and ketone (0.5 mmol) were sequentially introduced through an injection port. The autoclave was then pressurized to 40 bar H2 and the reaction mixture stirred at 120 C for 12 h. After cooling down to room temperature and subsequently releasing the H2 pressure in a fumehood, the mixture was concentrated and purified by chromatograph on a silica-gel column. The conversion of the product was determined by GC. |
83% | With sodium tetrahydroborate; In methanol; at 20℃; for 4h; | For a typical reaction, NaBH4 (1.0g, 26.8mmol) was added to a stirred solution of 1-pentanophenone (4.4g, 26.8mmol) in dry methanol (30mL). The exotherm was controlled by an ice bath. The suspension was stirred at room temperature for 4h, monitored by TLC. After the reaction was quenched by an addition of water (20mL), the methanol was removed under vacuum and the residue was extracted with ethyl acetate (3×30mL). The combined organic phases were washed with brine (20mL), dried over MgSO4 and then filtered. The organic solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate, 3:1) to give rac-4a (3.8g, 83%). The 1H NMR spectra of alcohols 3a,24 4a,24 5a,24 6a,24 7a,25 8a,26 9a,27 were all in agreement with those reported in the literature. |
60% | With Al(3+)*C3H7O(1-)*C50H66O4(2-); isopropyl alcohol; In hexane; toluene; at 20℃; for 12h; | General procedure for conducting MPV reduction: In 5 mL of anhydrous toluene (freshly distilled over sodium benzophenone ketyl), 1,3-bis-substituted calix[4]arene (e.g., for 1,3-bispropoxy calix[4]arene, 73 mg, 0.1 mmol, 10 mol%) is dissolved. To this solution, Me3Al (40 muL, 0.1 mmol, 10 mol%, 25% w/w solution in hexane) is added under Ar. Gaseous methane bubbles indicate the formation of methylaluminum calix[4]arene complex, which upon treatment with alcohol forms the active MPV catalyst and evolves methane. A 5 mL solution of alcohol (e.g., 300 muL, 240 mg, 4 mmol, 4 equiv. anhydrous 2-propanol) and substrate ketone (e.g., 155 mg, 1 mmol, 1 equiv. alpha-chloroacetophenone) in toluene is added. The reaction is subsequently performed at room temperature and is monitored by 1H NMR spectroscopy. |
With sodium hydroxide; In diethyl ether; water; | PREPARATION 13 1-Phenyl-1-pentanol To a stirring suspension of 1.20 g of lithium aluminum hydride in 100 mL of diethyl ether under an argon atmosphere at 0 C. is slowly added a solution of 4.40 mL of commercially available <strong>[1009-14-9]valerophenone</strong> in 5.0 mL of diethyl ether over 10 minutes. After 0.5 hours the grey suspension is warmed to room temperature. After 1 hour the reaction mixture is re-cooled to 0 C. and slowly treated with 1.25 mL of water followed by 5.50 mL of 1N sodium hydroxide. After 1 hour the resulting white precipitant is filtered through a pad of magnesium sulfate with diethyl ether washings. The filtrate is concentrated under reduced pressure to afford 4.5 g of 1-phenyl-1-pentanol as a clear, colorless oil. This product may be used directly in the next reaction without further purification. Physical characteristics are as follows: 1 H NMR delta 7.31, 4.65, 1.95, 1.82-1.68, 1.40-1.18, 0.87. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With hydrogenchloride; dihydrogen peroxide; sodium bromide; In water; at 20℃; | At room temperature, 16.2 g (0.1 mol) of <strong>[1009-14-9]valerophenone</strong> and 30.9 g (0.3 mol) of sodium bromide were added to a 500 mL round bottom flask, and after stirring,Add 24g (0.2mol) of 30% hydrochloric acid, and slowly add 19g (0.15mol) of 30% hydrogen peroxide. After the end of the addition, continue the reaction for 1~2h.After the end of the TLC monitoring reaction, the stirring was stopped, and the layers were allowed to stand, washed with saturated sodium carbonate and saturated brine, and the organic phases were combined.After concentration, it was dried over anhydrous magnesium sulfate to give alpha-bromo<strong>[1009-14-9]valerophenone</strong> as a bright yellow oily liquid, yield 95%, purity 98% (HPLC method). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With oxygen; In 1,3,5-trimethyl-benzene; at 60℃; under 760.051 Torr; for 12h; | The typical reaction steps are as follows:1 mmol of the starting alcohol of the reactant column shown in Table 2,OH - Ni3In-LDH 14 mg,Mesitylene 5mL were added to the reactor,Into the oxygen,Atmospheric reaction,The reaction was stirred at 60 for a certain period of time.The solid catalyst was removed by filtration,Using gas chromatography internal standard method (chlorobenzene as internal standard) to analyze the content of liquid products,Calculate yield. |
86% | With oxygen; caesium carbonate; In alpha,alpha,alpha-trifluorotoluene; at 105℃; for 20h;Air atmosphere; Ionic liquid; | The oxidation of 1-phenyl-1-pentanol (1a) is representative (Table 2, entry 1): BMI-PF6 (85 mg, 0.30 mmol), 1-phenyl-1-pentanol (1a, 33 mg, 0.20 mmol), Cs2CO3 (33 mg, 0.10 mmol), and trifluoromethylbenzene (0.10 mL) were placed in a reaction flask with a reflux condenser and a drying tube lined with calcium chloride. The resulting mixture was stirred for 20 h at 105 C. The reaction mixture was diluted with ethyl acetate and poured into water. The mixture was extracted with ethyl acetate three times. The combined organic layer was dried over Na2SO4, filtered through a pad of neutral alumina, and concentrated under reduced pressure. Purification by column chromatography on silica gel with hexane/ethyl acetate (10:1, v/v) as an eluent afforded 1-phenyl-1-pentanone (2a, 28 mg, 0.17 mmol) in 86% yield. |
83% | With magnesium sulphate; vanadyl(IV) sulphate pentahydrate; 4-nitrophenyl(phenyl)methanol; 4,4'-di-tert-butyl-2,2'-bipyridine; In water; at 0 - 90℃; under 750.075 Torr; for 120h; | General procedure: VOSO4·5H2O (126.5 mg, 0.5 mmol), 4,4?-di-tert-butyl-2,2?-bipyridyl (268.4 mg, 1 mmol), and p-nitrobenzhydrol (229.3 mg, 0.05 mmol) were placed in a 100 mL round-bottomed flask, and then water (50 mL) was added. Next, the mixture was stirred, and then anhydrous MgSO4 (18.06 g, 150 mmol) was slowly added into the mixture (cooling by ice water). After that, substrate (10 mmol) was added into the mixture at room temperature, and the mixture was stirred at 90 C for the appropriate time under open-air atmosphere. After the reaction, the mixture was extracted with ethyl acetate and dried over anhydrous MgSO4. The extracts were concentrated in vacuo. Purification of the products was carried out by silica gel column chromatography using hexane and diethyl ether as eluent to afford the analytically pure ketones. In Table 7 (entries 3, 7, and 8), crude products were purified by recrystallization with ethyl acetate in refrigerator, afforded analytically pure ketones. The product was identified by comparison with the commercially available sample using 1H NMR spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87% | With aluminum (III) chloride; In dichloromethane; at 0 - 40℃; for 2h; | Will be 156g of benzene,900 mL of dichloromethane and146.5g of anhydrous aluminum chloride was added toIn a 2L three-necked flask, after cooling to 0-5 C,Slowly add 120.5 g of n-pentanoyl chloride,The dropping process maintains an internal temperature of 0-10 C.After the completion of the dropwise addition, the temperature was raised to 40 C, and the reaction was stirred for 2 hours.Under ice cooling, 500 mL of 1N hydrochloric acid solution was slowly added dropwise, and after the addition was completed, the liquid was separated. The aqueous phase was extracted again with 400 mL of DCM.The organic phases were combined and concentrated under reduced pressure to give 142 g of phenylpentanone in a yield of 87%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With iodine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 22% 2: 26% 3: 36% 4: 30% | In hexane at 0℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With silver tetrafluoroborate; diethoxymethylane; C26H29N3O2*Cl(1-)*Ir(1+)*C8H12; at 20℃; for 20h; | General procedure: A flask was charged with azolium salt L12 (0.02 mmol, 9.1 mg),Ag2O (0.01 mmol, 2.4 mg) and CH2Cl2(1 mL). After stirring the resulting mixture at room temperature for 2 h in the dark, CH2Cl2 was removed in vacuo. Then, a THF (1 mL) solution of [IrCl(cod)]2(0.01 mmol, 6.9 mg) was added to the reaction vessel. The resulting mixture was stirred at room temperature for an additional 4 h in the dark, filtered through a membrane filter, and evaporated to dry-ness in vacuo. Subsequently, to the resulting flask containing yellow solid of the unpurified IrCl(cod)(NHC) complex, a solution of AgBF4(0.025 mmol, 4.9 mg) in CPME (2 mL) was added, and then stirred at room temperature for 1 h. Finally, propiophenone (0.5 mmol,66 mg) and (EtO)2MeSiH (2.25 mmol, 294 mg) were added to the resulting CPME solution (see Appendix A. Supplementary data fordetails). After stirring at room temperature for 20 h under open-air conditions, K2CO3(2 mg) and MeOH (2 mL) were added. Then, the resulting mixture was stirred at room temperature for 2 h. Afterevaporation of the solvents, the residue obtained was purified bycolumn chromatography on silica gel (Et2O/n-hexane = 3:7) to give(S)-1-phenyl-1-propanol (61 mg, 91% isolated yield). The ee was measured by chiral GLC. |
97% | With D-glucose; In aq. phosphate buffer; at 28℃; for 4h;pH 7.0;Microbiological reaction; | General procedure: Pichia glucozyma CBS 5766 was cultured using malt extract +0.5% yeast extractmedium (malt broth, yeast extract 5 g/L, pH 6.0) in a 3.0 L fermenter with 1.0 Lof liquid medium for 24 h, at 28 C and agitation speed 100 rpm. Cells fromsubmerged cultures were harvested by centrifugation and washed with 0.1 Mphosphate buffer, pH 7.0. Reductions were carried out in 100 mL screw-cappedtest tubes with a reaction volume of 50 mL with cells (2.5 g, dry weight)suspended in 0.1 M phosphate buffer, pH 7.0 containing 50 g/L of glucose. After30 min of incubation, substrates (20 mM) were added and the incubationcontinued for 24 h under magnetic stirring. When the reaction was over, pH wasbrought to pH 1 by the addition of 1 M HCl and 35 mL of EtOAc was added andthe resulting mixture was shaken and centrifuged; the aqueous phase wasextracted twice more with 35 ml of EtOAc. The organic phases were collectedand dried over Na2SO4 and the solvent was evaporated. The crude residues werepurified by flash chromatography. |
45% | With water; In ethanol; for 168h;modified Czepak Dox medium; | General procedure: The substrates (each 100 mg) in EtOH (1 mL) were added to the culture and shaken for the periods shown in the Tables. Substrate and organism controls were also run simultaneously in each case. At the end of fermentation, the mycelial mass was filtered from the culture medium. The filtrate was extracted with chloroform (2 × 50 mL), washed with H2O (2 × 20 mL) and dried. Removal of the solvent gave a residue which on preparative thin-layer chromatography (silica gel, EtOAc/hexane) furnished the respective product alcohols. The spectral and chiroptical data of compounds 1b, 2b, 4b, 7b and 9b matched those reported by us previously.9c |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With ammonium iodide; RhH(CO)(PPh3)3; C52H58N4P2; isopropyl alcohol; potassium hydroxide; at 65℃; for 4h; | General procedure: Chiral macrocycles 1 and 2 were synthesized using the same procedure we previously reported [25]. Under air atmosphere, the complex RhH(CO)(PPh3)3 (9.2 mg, 0.01 mmol), (R, R, R', R')-2 (8.0 mg,0.01 mmol), and NH4I (22.0 mg, 0.15 mmol) were placed in a tube equipped with a Teflon-coated magnetic stirring bar. Then, iPrOH was added and the mixture was stirred at 65 C for 30 min. Next, an appropriate amount of KOH/iPrOH solution was added, and the mixture was continually stirred for another 10 min. Later, ketone was introduced, and the mixture was stirred at the desired temperature for the required reaction time. At the end of experiment, the reaction products were determined by GC using a chiral CP-Chiralsil-Dex CB column. |
94%Chromat. | With bis(triphenylphosphine)carbonyliridium(I) chloride; C70H73N4P3; potassium hydroxide; In isopropyl alcohol; at 40℃; for 2h;Inert atmosphere; | General procedure: Under nitrogen atmosphere, the catalyst precursor IrCl(-CO)(PPh3)2 (3.9 mg, 0.005 mmol) and (R,R,R,R)-3 (5.3 mg,0.005 mmol) were placed in a tube equipped with a Teflon-coated magnetic stirring bar. i-PrOH was then added and the mixture was stirred at 40 8C for 20 min. An appropriate amount of KOH/i-PrOH solution was then added, and the mixture was continually stirredfor another 20 min. Next, ketone (0.5 mmol) was introduced and the mixture was stirred at 40 8C for the required reaction time. At the end of the reaction, the product was analyzed by GC using achiral CP-Chirasil-Dex CB column. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 3 % Chromat. 2: 94 % Chromat. | With lithium In tetrahydrofuran for 0.75h; Ambient temperature; Irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran at -78℃; for 0.00833333h; Title compound not separated from byproducts; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With cerium(III) sulphate; barium bromate In lithium hydroxide monohydrate; acetonitrile for 6h; Heating; | |
85% | With potassium permanganate; iron(III) chloride In propan-2-one at -78 - 20℃; for 16h; | |
75% | With (4s,6s)-2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile; oxygen; tetra-n-butylammonium azide In acetonitrile at 25℃; for 24h; Irradiation; |
67% | With oxygen; 2,6-lutidinium perchlorate In acetonitrile at 20℃; for 12h; Electrolysis; | |
48% | With tert.-butylhydroperoxide In acetonitrile at 80℃; for 2h; | |
55 % Chromat. | With ethoxylated β-cyclodextrin; dihydrogen peroxide; iron nitrate (III) at 65℃; for 1h; | |
51 %Chromat. | With 9-(benzoyl(cyclohexyl)carbamoyl)-10-phenylacridinium perchlorate In acetonitrile at 20℃; for 18h; Irradiation; Green chemistry; | |
With anthraquinone-2-sulfonic acid sodium salt In lithium hydroxide monohydrate; acetonitrile at 20℃; Flow reactor; Photolysis; | Continuous flow procedure General procedure: The reaction solution is prepared by dissolving Ethylbenzene (0.2 g, 1.9 mmol, 1.0 equiv) and Sodium anthraquinone sulfonate (0.12 g, 20 mol%) in a 70% v/v acetonitrile/purified water mix (200 mL 1000 Vols). Flow experiments were performed using a 20 m Diba Omnifit PTFE Coil with a 1 mm I.D. The tubing was wrapped around a 3D printed scaffold constructed from PLA. Liquid was supplied to the reactor with an Ismatec Reglo 4-Channel peristaltic pump, equipped with 1.42 mm ID Tygon tubing. Compressed gas was supplied to the reactor with a SLA5800 seires Brookes Instruments mass flow controller (MFC). A cartridge type 5 PSI back pressure regulator (BPR) was fitted to the end of the reactor. Ultrafine bubbles were supplied by FBG-OS type 1 unit from Process Maximize Technologies. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: sodium benzoate With chloroformic acid ethyl ester In tetrahydrofuran at 20℃; for 0.25h; Stage #2: n-butylzinc iodide In tetrahydrofuran at 70℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 3 percent Chromat. / Li / tetrahydrofuran / 0.75 h / Ambient temperature; Irradiation 2: 66 percent Chromat. / Li / tetrahydrofuran / 1.5 h / Ambient temperature; Irradiation | ||
Multi-step reaction with 2 steps 1: 40 percent Chromat. / nBuI, Li / tetrahydrofuran / 3.17 h / Ambient temperature; Irradiation 2: 66 percent Chromat. / Li / tetrahydrofuran / 1.5 h / Ambient temperature; Irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen In toluene at 80℃; for 24h; Autoclave; chemoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With titanium tetrachloride; zinc In tetrahydrofuran for 2.5h; Inert atmosphere; Reflux; | 4.1.1. Method A. McMurry reductive coupling reaction General procedure: General procedure: To a stirred suspension of zinc powder (31 mmol) in dry THF (30 mL) was added TiCl4 (14 mmol), under Ar, at 10 C. When the addition was complete, the mixture was warmed to room temperature and then refluxed. After titanium reagent was refluxed for 2.5 h, the mixture was cooled to 0 C and then a solution of 4,4'-hydroxybenzophenone (2.3 mmol)and substituted-phenone (6.7 mmol) in dry THF (40 mL) at 0 C was added to the mixture. Upon completion of addition of solution, the mixture was refluxed in the dark for 2.5 h, cooled to room temperature (25 C); and quenched with 10% aqueous potassium carbonate(50 mL) and extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. |
79% | With titanium tetrachloride; zinc In tetrahydrofuran at -10 - 0℃; for 2.5h; Inert atmosphere; Reflux; | 2 Method A. McMurry Reductive Coupling Reaction. General procedure: To a stirred suspension of zinc powder (31 mmol) in dry THF (30 mE) was added TiC14 (14 mmol), under Ar, at 10° C. When the addition was complete, the mixture was warmed to room temperature and then refluxed. Afier titanium reagent was refluxed for 2.5 h, the mixture was cooled to 0 degree C. and then a solution of 4,4’-hydroxybenzo- phenone (2.3 mmol) and substituted-phenone (6.7 mmol) in dry THF (40 mE) at 0° C. was added to the mixture. Upon completion of addition of solution, the mixture was refluxed in the dark for 2.5 h, cooled to room temperature (25° C.); and quenched with 10% aqueous potassium carbonate (50 mE) and extracted with EtOAc. The organic layer was washed with brine, dried over Mg504, and concentrated in vacuo. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With 3-methylpyridin-2-ylamine; chlorobis(ethylene)rhodium(I) dimer; ethyl crotonate; 1,3-bis(2,4,6-trimethylphenyl)4,5-dimethyl-1,3-dihydro-2H-imidazol-2-ylidene; water; toluene-4-sulfonic acid In 2-methyltetrahydrofuran at 150℃; for 120h; Inert atmosphere; Glovebox; Sealed tube; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With 1,10-Phenanthroline; potassium <i>tert</i>-butylate; nickel dibromide In toluene at 140℃; for 36h; Schlenk technique; Sealed tube; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In neat liquid Photolysis; | 18 4.1. Typical experimental procedure General procedure: All the α-bromo ketones tested for the photolysis experiment were prepared by bromination of the corresponding ketones using CuBr2. The synthetic procedure has been described in our previous paper [7]. Photolysis in solution phase was done with 0.01M solution of the ketones after purging Ar gas through the solution for a few minutes using a typical photolysis setup whose light source was the Pyrex filtered light of a 450W Hanovia medium pressure mercury arc lamp. Photolysis in no solvent condition was done in much simpler way. A sample vial containing either liquid or sold sample was hung next to the photolysis setup and irradiated until completion. For solid samples, the reaction times could be shortened significantly by irradiating the sample doped on a thin glass plate which was simply prepared by dropping acetone solution of a given compound onto any thin glass plate and evaporating the solvent. Structural identification of photoproducts was done either by comparing them with authentic samples when they were available, or by typical spectroscopic identification procedures. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetonitrile Photolysis; | 18 4.1. Typical experimental procedure General procedure: All the α-bromo ketones tested for the photolysis experiment were prepared by bromination of the corresponding ketones using CuBr2. The synthetic procedure has been described in our previous paper [7]. Photolysis in solution phase was done with 0.01M solution of the ketones after purging Ar gas through the solution for a few minutes using a typical photolysis setup whose light source was the Pyrex filtered light of a 450W Hanovia medium pressure mercury arc lamp. Photolysis in no solvent condition was done in much simpler way. A sample vial containing either liquid or sold sample was hung next to the photolysis setup and irradiated until completion. For solid samples, the reaction times could be shortened significantly by irradiating the sample doped on a thin glass plate which was simply prepared by dropping acetone solution of a given compound onto any thin glass plate and evaporating the solvent. Structural identification of photoproducts was done either by comparing them with authentic samples when they were available, or by typical spectroscopic identification procedures. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | Stage #1: dicyclohexyl-carbodiimide; benzoic acid In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: n-butyllithium In tetrahydrofuran; hexane at -20℃; for 0.5h; Inert atmosphere; | B: General Experimental Procedure for the Synthesis of Ketone from Carboxylic Acid. Method A General procedure: To a stirred solution of carboxylic acid 1 (1 mmol) in THF (3 mL), DCC (1 mmol) was added at room temperature under N2 atmosphere. After 1 h, the mixture was cooled to -20 °C and n-BuLi (2 mmol) was added to the reaction mixture indrop wise. After 0.5 h the reaction was quenched with saturated NH4Cl solution (5 mL) at -20 C. The mixture was warmed to room temperature and extracted with ethyl acetate (10 mL ×3). The combined organic layers were washed with water (20 mL × 3), brine (20 mL) and finally dried over MgSO4. The volatiles are evaporated under reduced pressure to get a crude mass which was then purified by column chromatography on silica gel (EtOAc: petroleum ether = 1:9) to obtain pure 3. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54 % | With oxygen; rose bengal; sodium hydrogencarbonate In water; acetonitrile at 55℃; Irradiation; | 4 Example 4 2-methylpentanoic acid 1-oxo-1-phenyl-2-pentyl ester (-3ad) Add compound (I) valerophenone (49mg, 0.3mmol, 1.0equiv) in the test tube equipped with magnetic stirring,Sodium bicarbonate (25mg, 0.3mmol, 1.0equiv), Rose Bengal (15mg, 0.015mmol, 0.05equiv), compound () 2-methylpentanoic acid (209mg, 1.8mmol, 6.0equiv), add water (0.3 mL), acetonitrile (1.0 mL), oxygen replacement. The reaction system was irradiated with a blue light with a power of 3W, and the reaction was stirred at 55°C for 48 hours. After the reaction was completed, an excess of saturated sodium bicarbonate solution was added to quench (10 mL), then ethyl acetate (20 mL) and a small amount of water (2 mL) were added. , separated, and then extracted 3 times with ethyl acetate (15mLx3), the combined organic layer was dried with 7.5g of anhydrous Na2SO4 and concentrated under reduced pressure, using petroleum ether/ethyl acetate with a volume ratio of 40:1 on a silica gel column The crude product was purified to obtain the target product with a yield of 54% and an HPLC purity of 98.0%. |
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Sorry,this product has been discontinued.
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