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CAS No. : | 3376-59-8 | MDL No. : | MFCD01084321 |
Formula : | C10H12O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | SFCPXHKCMRZQAC-UHFFFAOYSA-N |
M.W : | 196.20 | Pubchem ID : | 137911 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.3 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 49.66 |
TPSA : | 66.76 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.81 cm/s |
Log Po/w (iLOGP) : | 1.8 |
Log Po/w (XLOGP3) : | 0.97 |
Log Po/w (WLOGP) : | 0.2 |
Log Po/w (MLOGP) : | 0.82 |
Log Po/w (SILICOS-IT) : | 1.01 |
Consensus Log Po/w : | 0.96 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.65 |
Solubility : | 4.35 mg/ml ; 0.0221 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.96 |
Solubility : | 2.15 mg/ml ; 0.011 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.8 |
Solubility : | 3.12 mg/ml ; 0.0159 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.25 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-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 |
---|---|---|
With sodium periodate; In dichloromethane; water; at 20℃; for 2h; | Example 3 benzoyloxyacetaldehyde This known intermediate was prepared by a previously unreported method from the known 1-benzoyl glycerol.. Thus, 50 g of the latter in a mixture of 500 ml of CH2Cl2 and 25 ml of H2O was treated portion-wise with 80 g of NaIO4 under vigorous stirring at room temperature.. After addition, stirring was continued for 2 h after which time 100 g of MgSO4 was added and stirring continued for 30 min.. The mixture was filtered, the filtrate evaporated in vacuo and the residue distilled in vacuo to yield 26 g of pure (VII) b.p. 92-94/0.25 mm. 1H NMR (200 MHz; TMS as internal reference) delta(ppm in CDCl3):9.71 (s, 1H; -CHO);8.11 (d, 2H: aromatic);7.60 (m, 1H; aromatic);7.46 (m, 2H; aromatic);4.88 (s, 2H; -CH2CHO). | |
With sodium periodate; In dichloromethane; water; at 20℃; | Oxidation of Benzoyl glycerol to Benzoyloxy acetaldehyde Compound VTo 160 g (0.816 moles) of Benzoyl glycerol dissolved in 1.6 L of DCM and 80 mL of DM water, 192 g (0.897 moles) of NaIO4 was added in portions at room temperature. When the reaction was complete, the solid was filtered and the filtrate was concentrated to get the desired product.MS: M++1=1651H NMR (CDCl3): delta 4.88 (s, 2H), 7.25-8.11 (m, 5H), 9.7 (s, 1H) | |
75 g | With sodium periodate; In dichloromethane; water; at 20 - 25℃; for 4h; | 85 g of the top step oil was dissolved in 400 ml of dichloromethane and 40 ml of water.80 g of sodium periodate (1.0 eq) was added in 8 portions at 20-25 C.Continue to react for 4 hours.The solid was filtered and the filtrate was concentrated.Get 75g of oil,It does not require purification and is directly fed to the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
96% | With methanesulfonic acid; at 35℃; for 1h;Large scale; | Add 8.5 kg of <strong>[3376-59-8]glycerol monobenzoate</strong> and 10 kg of acetone to the reaction kettle.The catalyst methanesulfonic acid was 0.025 kg, and the reaction was completed at 35 C for 60 min.The catalyst was recovered by water extraction, and excess acetone was recovered by atmospheric distillation to obtain acetone glycerol benzoate 9.8 kg, yield 96%, purity: 98.5%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97.5% | With methanesulfonic acid; In toluene; at 120℃; for 2.5h;Large scale; | Add 10 kg of glycerol and 13.26 kg of benzoic acid to the reaction kettle.Methane sulfonic acid catalyst was added 0.05 kg of toluene and the agent with 2kg,The reaction was completed at 120 oC for 150 min.The catalyst was extracted and recovered by water, and the raw material was removed by distillation under reduced pressure to give an intermediate glycerol mono benzoate, yield 97.5%, purity 99%. |
99%Chromat. | With poly(ethylene glycol) 1000 based dicationic acidic ionic liquid; In toluene; at 80℃; for 1h;Ionic liquid; | General procedure: Aromatic acids (2 mmol) and alcohols (3 mmol) were added into a 10 mL tube reactor preloaded with PEG1000-DAIL (2 mL) and toluene (2 mL). The reaction mixture was stirred thoroughly at 80C for 1 h. After the completion of reaction, the mixture separated into two phases at room temperature, the upper phase was decanted for analysis and the below phase was reused for the next time directly or after removing water under vacuum at 80C for 1 h. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With hydrogenchloride; In tetrahydrofuran; water; at 45 - 50℃; | Preparation of benzoyl glycerol Compound IV225 g (0.95 moles) of benzoylated 1,2-isopropylidene glycerol dissolved in 1.125 L of THF was heated to 45-50 C. with 45 mL of 2N HCl. When the reaction was complete, the mixture was cooled to room temperature, neutralized with 11 g of NaHCO3, stirred, and filtered. The THF in the filtrate was distilled under vacuum (100-150m of Hg). Yield: 187 gTwice stirring it in 1.1 L of 5% ethylacetate/hexane for 30 minutes each time re-crystallized the product.Yield: 165 g (88%)MS: M+1=1971H NMR (CDCl3): delta 3.21 (bs, 2H), 3.6-3.74 (m, 2H), 4.03-4.10 (m, 1H), 4.37-4.39 (d, 2H), 7.25-8.03 (m, 5H) |
90%Chromat. | With hexabromoacetone; In 1,2-dichloro-ethane; at 20℃; for 0.5h;UV-irradiation; | General procedure: To a 25-mL quartz tube was added 1 mmol (152 mg) of benzaldehyde dimethyl acetal, 0.025 mmol (13 mg) of HBA, and 5 mL of solvent. The reaction mixture was stirred and irradiated by a home-made UV reactor for 1 min at room temperature. To quantify the product using GC, 1 mmol (154 mg) of biphenyl was added as an internal standard. The sample was diluted with methanol and injected into the GC equipped with a SGE BP1 column. To obtain an isolated yield, the solvent was evaporated and the crude product was purified using a silica gel column. |
5 g | With hydrogenchloride; In tetrahydrofuran; at 0 - 50℃; for 1.66667h; | Intermediate-4 (10g, 0.04 mol) was dissolved in THF (50mL), and to this solution 2N HCI (2 mL) was added at 0-5C. Stirring was continued for 10 min and the reaction was further heated to 50C for 1.5h. After completion of reaction, the reaction mass was concentrated under reduced pressure and the crude product was purified by column chromatography (silica gel 230-400) using Etylt Acetate-Hexane. Purification resulted in 5g of pure Compound 9 with HPLC purity of about 95%. |
85 g | With hydrogenchloride; In tetrahydrofuran; water; at 20 - 50℃; for 2h; | 90 g of the oil obtained in the above step was dissolved in 200 ml of tetrahydrofuran, and 40 ml of 2N hydrochloric acid was added dropwise.After the drip is heated to 45-50 C,After stirring for 2 h, it was stirred at room temperature overnight.After the reaction, it was neutralized with 5 g of sodium hydrogencarbonate.filter. The filtrate is evaporated to dryness.Obtained 85g of oil,It does not require purification and is directly fed to the next reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In pyridine; chloroform; water; | To a solution of 35.5 g (181 mmol) of (-)-1-benzoyl glycerol (G) in 250 ml of dry pyridine at 0 C. is added 83 g (433 mmol) of p-toluenesulfonyl chloride. The mixture is stirred at 0 C. for 15 minutes and then stored in a refrigerator for 144 hours. After cooling the reaction mixture to 0 C., 10 ml of water are added, the mixture is stirred for 10 minutes, and then poured into excess water. The aqueous solution is separated from the gummy product, and extracted with chloroform. The gummy residue is dissolved in chloroform and the combined chloroform solution is washed sequentially with 3 N hydrochloric acid, water, 5% sodium bicarbonate solution, and water. The chloroform solution is dried over Na2 SO4 and concentrated under reduced pressure to obtain a solid which, upon recrystallization from absolute ethanol, gives 65.5 g (130 mmol, 72%) of (-)-1-benzoyl-2,3-di-p-toluenesulfonyl glycerol (see Formula (H) in Scheme 2), m.p. 105-106 C. [alpha]D2 -22.7 (c, 5.92, CHCl3). 1 H NMR (CDCl3) delta8-7 (m, 13H); 4.9 (m, 1H); 4.45 (d, 2H, J=6 Hz); 4.35 (d, 2H, J=5 Hz); 2.42 (s, 3H); 2.38 (s, 3H). 13 C NMR (CDCl3) 165.162, 145.136, 133.108, 132.466, 131.649, 129.430, 128.671, 128.087, 127.678, 75.306, 66.899, 61.994, 21.591 ppm. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With 4-methylmorpholine N-oxide; In water; acetone; at 100℃; for 3h; | General procedure: alkenesTo a stirred solution of alkene (1, 1 mmol) in a mixture ofacetone:H2O 2:1 (3 mL) in a pressure tube, OsO2-Fe3O4(10 mg,0.08% of osmium) and NMO (234 mg, 2 mmol) were added. Theresulting mixture was stirred at 100C during 3 h. The catalyst wasremoved by a magnet and the resulting solution was extracted withether. The organic phases were dried over MgSO4, and the solventswere removed under reduced pressure. The product was usuallypurified by chromatography on silica gel (hexane/ethyl acetate)to give the corresponding products 2 or 4. Physical and spectro-scopic data as well as literature for all compounds are includedas Appendices A and B. FT-IR spectra were obtained on a Nicoletimpact 400D spectrophotometer. NMR spectra were recorded ona Bruker AC-300 apparatus (300 MHz for1H and 75 MHz for13C)using CDCl3as a solvent and TMS as internal standard for1H and13C; chemical shifts are given in (parts per million) and couplingconstants (J) in Hertz. Mass spectra (EI) were obtained at 70 eVon a spectrometer Agilent GC/MS-5973N, giving fragment ions inm/z with relative intensities (%) in parentheses. Thin layer chro-matography (TLC) was carried out on DC-Fertigfolien ALUGRAMplates coated with a 0.2 mm layer of silica gel; detection by UV254light, staining with phosphomolybdic acid [25 g phosphomolybdicacid, 10 g Ce(SO4)2·4H2O, 60 mL of concentrated H2SO4and 940 mLH2O]. Column chromatography was performed using silica gel 60of 35-70 mesh. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a stirred suspension of sodium hydride (0.273 g, 0.68mol, 60% in oil) in anhydrous THF (100 mL) under a nitrogenatmosphere at 0C, a solution of (±)-1 (33.3 g, 0.17 mol)in anhydrous THF (150 mL) was added over a period of 1 hmaintaining the internal temperature below 5C. After stirringat room temperature for 12 h, 1-bromotetradecane(187.7 g, 0.68 mol) was added at 0C over a period of 1 h.After complete addition, the reaction mixture was stirred for2 h at room temperature and this was gradually increasedwhen reaching reflux, and then stirred for 24 h. A LiOH solution(10% wt/v,100 mL) was added, and stirring and thetemperature were maintained for 12 h. The mixture was dilutedwith saturated ammonium chloride (300 mL). Theaqueous layer was extracted with dichloromethane (700 mL),washed with water (3 150 mL), and dried over Na2SO4.The unreacted 1-bromotetradeane was removed by distillationunder reduced pressure (1 mm of Hg and 125 C). Theresidue was purified by column chromatography eluting withhexane to obtain (±)-2 (39.5 g, 48%) as a white solid, mp.43-45 C (lit. 42.5-43.5C) [18]. 1H NMR (CDCl3, 200MHz) 0.87 (t, J = 6.7 Hz, 6H, C12-C12H3), 1.25 (br s, 44H,C11-C11H2), 1.58-1.61 (m, 4H, C10-C10H2), 3.37-3.73(m, 9H; C9-C9-C3-C2H2, C1H); 13C NMR (CDCl3,200MHz) 14.1 (C16-16), 22.8 (C15-15), 27.6 (C12-12),29.1-29.5 (C13-13), 29.7 (C11-11), 32.5 (C14-14), 32.8(C10-10), 64.3 (3C), 65.5 (C1), 71.0 (C9), 70.9(C9),72.0(C3), 78.4 (C2). EI-LR-MS, m/z, M+: 484. | ||
To a stirred suspension of sodium hydride (0.273 g, 0.68mol, 60% in oil) in anhydrous THF (100 mL) under a nitrogenatmosphere at 0C, a solution of (±)-1 (33.3 g, 0.17 mol)in anhydrous THF (150 mL) was added over a period of 1 hmaintaining the internal temperature below 5C. After stirringat room temperature for 12 h, 1-bromotetradecane(187.7 g, 0.68 mol) was added at 0C over a period of 1 h.After complete addition, the reaction mixture was stirred for2 h at room temperature and this was gradually increasedwhen reaching reflux, and then stirred for 24 h. A LiOH solution(10% wt/v,100 mL) was added, and stirring and thetemperature were maintained for 12 h. The mixture was dilutedwith saturated ammonium chloride (300 mL). Theaqueous layer was extracted with dichloromethane (700 mL),washed with water (3 150 mL), and dried over Na2SO4.The unreacted 1-bromotetradeane was removed by distillationunder reduced pressure (1 mm of Hg and 125 C). Theresidue was purified by column chromatography eluting withhexane to obtain (±)-2 (39.5 g, 48%) as a white solid, mp.43-45 C (lit. 42.5-43.5C) [18]. 1H NMR (CDCl3, 200MHz) 0.87 (t, J = 6.7 Hz, 6H, C12-C12H3), 1.25 (br s, 44H, C11-C11H2), 1.58-1.61 (m, 4H, C10-C10H2), 3.37-3.73(m, 9H; C9-C9-C3-C2H2, C1H); 13C NMR (CDCl3,200MHz) 14.1 (C16-16), 22.8 (C15-15), 27.6 (C12-12),29.1-29.5 (C13-13), 29.7 (C11-11), 32.5 (C14-14), 32.8(C10-10), 64.3 (3C), 65.5 (C1), 71.0 (C9), 70.9(C9),72.0(C3), 78.4 (C2). EI-LR-MS, m/z, M+: 484. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With lipozyme; In 1,4-dioxane; at 55℃; for 48h;Enzymatic reaction; | To a 1,4-dioxane solution (200 mL) containing glycerol(18.4 g, 0.20 mol) and vinyl benzoate (29.6 g, 0.20 mol),Lipozyme (30 g) was added, and the mixture was stirred for48 h at 55C. After removal of the enzyme by filtration, thereaction mixture was evaporated under reduced pressure andthe residue was partitioned between saturated brine and dichloromethane(100 mL each), and extracted with dichloromethane(3 60 mL). The combined organic layer waswashed with saturated brine, and dried over anhydrousNa2SO4. The extract was washed with hexane to removeunreacted vinyl benzoate. Subsequently, the extract was vacuumdried, affording 36 g of (±)-1 (75% yield) as a colorlessoil. IR (KBr), cm-1: 3600 - 3100, 3050, 1700, 1300, 690; 1HNMR (200 MHz, CDCl3) 3.64-3.86 (2H, m, C3H2), 4.04-4.14 (1H, m, C2H), 4.39-4.57 (2H, m, C1H2), 7.40-7.52 (2H,m, 2C7H), 7.56 (1H, m, C8H), 8.02-8.13 (2H, m, 2C6H); 13CNMR (CDCl3, 200MHz) 63.8 (C3), 65.5 (C1), 70.6 (C2),128.6 (2C7), 129.4 (2C6), 130.7 (C5), 133.1 (C8), 166.5(C4). EI-LR-MS, m/z, M+: 196. |
75% | With Mucor miehei lipase (lipozyme); In 1,4-dioxane; at 55℃; for 48h;Enzymatic reaction; | To a 1,4-dioxane solution (200 mL) containing glycerol(18.4 g, 0.20 mol) and vinyl benzoate (29.6 g, 0.20 mol),Lipozyme (30 g) was added, and the mixture was stirred for48 h at 55C. After removal of the enzyme by filtration, thereaction mixture was evaporated under reduced pressure andthe residue was partitioned between saturated brine and dichloromethane(100 mL each), and extracted with dichloromethane(3 60 mL). The combined organic layer waswashed with saturated brine, and dried over anhydrousNa2SO4. The extract was washed with hexane to removeunreacted vinyl benzoate. Subsequently, the extract was vacuumdried, affording 36 g of (±)-1 (75% yield) as a colorlessoil. IR (KBr), cm-1: 3600 - 3100, 3050, 1700, 1300, 690; 1HNMR (200 MHz, CDCl3) 3.64-3.86 (2H, m, C3H2), 4.04-4.14 (1H, m, C2H), 4.39-4.57 (2H, m, C1H2), 7.40-7.52 (2H,m, 2C7H), 7.56 (1H, m, C8H), 8.02-8.13 (2H, m, 2C6H); 13CNMR (CDCl3, 200MHz) 63.8 (C3), 65.5 (C1), 70.6 (C2),128.6 (2C7), 129.4 (2C6), 130.7 (C5), 133.1 (C8), 166.5(C4). EI-LR-MS, m/z, M+: 196. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6%; 67% | With tetrabutylammonium benzoate; In acetonitrile; at 40℃;Green chemistry; | General procedure: Diols and polyol reactants (100 mg) were allowed to react with benzoic anhydride (1.1 equiv) in acetonitrile (1 mL) at 40C for 8-12 h in the presence of TBAOBz (0.2 equiv). The reaction mixture was directly purified by flash column chromatography (hexanes/EtOAc=2:1 to 1:1), affording the pure selectively protected derivatives. |
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