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CAS No. : | 505-52-2 | MDL No. : | MFCD00002740 |
Formula : | C13H24O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | DXNCZXXFRKPEPY-UHFFFAOYSA-N |
M.W : | 244.33 | Pubchem ID : | 10458 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.85 |
Num. rotatable bonds : | 12 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 68.15 |
TPSA : | 74.6 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.13 cm/s |
Log Po/w (iLOGP) : | 2.39 |
Log Po/w (XLOGP3) : | 3.74 |
Log Po/w (WLOGP) : | 3.45 |
Log Po/w (MLOGP) : | 2.4 |
Log Po/w (SILICOS-IT) : | 2.99 |
Consensus Log Po/w : | 2.99 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.92 |
Solubility : | 0.294 mg/ml ; 0.0012 mol/l |
Class : | Soluble |
Log S (Ali) : | -5.0 |
Solubility : | 0.00245 mg/ml ; 0.00001 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.09 |
Solubility : | 0.2 mg/ml ; 0.000818 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 1.98 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P273-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319-H412 | 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 |
---|---|---|
EXAMPLE 5 Tridecanedioic acid 338.58 g (1 mol) of erucic acid (purity 95%) were ozonized in analogy to Example 1 and then hydrogenation was carried out. The hydrogenation solution obtained in this way contained nonanal and tridecanealdehyde acid and was divided by distillation. For oxidation, the corresponding aldehyde fraction was employed and was oxidized at 14 bar in analogy to Example 1. 185 g of tridecanedioic acid per cycle were obtained with a purity of 95%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 20℃; for 16.0h;Inert atmosphere; | To a suspension of LiAlH4 (0.835 g, 22.00 mmol, 2.20 equiv) in THF (50 mL) was slowly added a solution of undecane-1,11-dioic acid (10; 2.443 g, 10.00 mmol, 1.00 equiv) in THF (100 mL) at 0 C. This mixture was stirred at r.t. for 16 h. The reaction was stopped by addition of a 30 wt% aqueous solution of citric acid at 0 C (100 mL). The mixture was extracted with Et2O (3 80 mL) and the combined organic phases were washed with H2O, dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The residue was dissolved in Et2O and washed again with H2O. The organic phase was dried over anhydrous Na2SO4 and the solvent was evaporated under reduced pressure. The product was used without further purification. Yield: 1.905 g (8.804 mmol, 88%); colourless solid; mp 74-75 C (lit.6b mp 75-76 C); Rf = 0.39 (cyclohexane/EtOAc, 2:3). IR (ATR): 3236, 2917, 2849, 1486, 1472, 1462, 1405, 1357, 1344, 1324, 1302, 1257, 1210, 1187, 1123, 1057, 1037, 1019, 1002, 973, 958, 920, 876, 831, 764, 731, 720, 687 cm-1. 1H NMR (CDCl3, 500 MHz): delta = 3.65 (t, J = 6.6 Hz, 4 H, 1-H, 13-H), 1.57 (quin, J = 6.6 Hz, 4 H, 2-H, 12-H), 1.38-1.25 (m, 20 H, 3-H to 11-H, OH). 13C NMR (CDCl3, 125 MHz): delta = 63.3, 33.0, 29.74, 29.73, 29.70, 29.6, 25.9. |
General procedure: Under an atmosphere of N2, a suspension of LiAlH4 (228 mg, 6.01 mmol, 11.6 equiv) in dry THF (6 mL) was stirred at rt for 5 min. The mixture was cooled to 0 C, and a solution of pentadecanolide (500 mg, 2.08 mmol, 1 equiv) in THF (6 mL) was added. The reaction mixture was brought to rt and then stirred at reflux temperature for 2 h. The mixture was cooled to 0 C and then an aqueous solution of NaOH (2 M, 2 mL) was added. A white precipitate was formed and the mixture was stirred at reflux temperature for 0.5 h. The mixture was extracted with Et2O (2 × 50 mL). The combined organic extracts were washed with brine (2 × 20 mL), dried (Na2SO4), and concentrated. High-vacuum drying gave 1,15-pentadecanediol (482 mg, 1.97 mmol, 95%) as a white solid; | ||
General procedure: Samples of 1,10-decanediol, DEDOL (98% pure) and 1,12-dodecanediol, DODOL (99% pure) fromSigma-Aldrich were used as received. Then, 1,11-undecanediol (UNDOL) and 1,13-tridecanediol(TRDOL) were synthesized from the corresponding dicarboxylic acids by a reduction procedurereported elsewhere [41]. First, N-methylmorpholine (1.01 mL, 9.24 mmol) and ethyl chloroformate(0.88 mL, 9.24 mmol) [42] were mixed with a dissolution (2 C) prepared with 1 g of undecanedioicacid (4.62 mmol) in 50 mL of THF. This mixture was stirred for 15 min and a precipitate ofN-methylmorpholine hydrochloride was obtained. This precipitate is filtered, washed with THFand mixed at 2 C with 7 mL of an aqueous sodium borohydride solution (0.56 g, 14.78 mmol). Then,120 mL of water was added after degassing the solution. Finally, ethyl acetate was used to obtainthe organic extract that, subsequently, was dried over sodium sulfate. Purified UNDOL is obtainedfor concentrating them under reduced pressure and recrystallized in ethyl ether. All this synthesiswas also used to obtain TRDOL but, in this case, 1,13-tridecanedioic acid was selected as the startingproduct. TRDOL was recrystallized in toluene instead of ethyl ether in order to evaluate possiblechanges on crystallite morphology of isostructural compounds. |
With lithium aluminium tetrahydride; In tetrahydrofuran; for 12.0h;Inert atmosphere; | To a solution ofbrassylic acid (2, 1.2210 g, 5mmol) in anhydrous THF(15 mL), LiAlH4 (0.5690 g, 15mmol) was added in dry threeneckedround-bottomed flask equipped in batches undernitrogen atmosphere at 0C. The mixture was stirred at roomtemperature for 12 h. After completion, the reaction wasquenched by 10% HCl aqueous solution in ice bath until gasproduction ceased.The organic layer was separated, filtered,and concentrated under reduced pressure. The residue waswashed with ethyl acetate and dried over anhydrous MgSO4.The extract was evaporated and dried to give crude 1,13-tridecanediol (3, 1.0818g) as white solid. 1H-NMR (CDCl3,500MHz) 3.61 (dd, , J = 11.0, 6.2Hz, 4H), 2.35 (s, 1H),2.26 (s, 1H), 1.62-1.50 (m, 4H), 1.39-1.20 (m, 18H); 13C-NMR(CDCl3, 125MHz) 77.2, 77.0, 76.7, 32.6(2), 29.5(3), 29.4(2),29.3(2), 25.6; HRMS (ESI-TOF) m/z: Calcd. for C13H29O2+217.2183 ([M + H]+). Found: 217.2205. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; for 2h;Reflux; | Tridecanedioic acid (2.8 g,0.01 mol), the thionyl chloride and (8 mL) was added, and refluxed in water bath for 2 hours.Then, the excess of thionyl chloride was distilled off under reduced pressure to give thetridecanedioic acid dichloride. | |
With thionyl chloride; for 2h;Reflux; | To tridecanedioic acid (2.8 g, 0.01 mol), thionyl chloride (8 mL) was added and the mixture was refluxed on a water bath for 2 hours. Thereafter, the excess thionyl chloride was distilled off under reduced pressure to obtain tridecanedioic acid dichloride. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride; at 0℃; for 15h;Inert atmosphere; Reflux; | To a solution of 42 (9.4 g, 38 mmol) in MeOH (383 mL) was addedSOCl2 (6.9 mL, 96 mmol) at 0 C. After stirring for 15 h under refluxconditions, the completion of the reaction was confirmed by TLC (3:1 nhexane/EtOAc). The reaction was quenched by the addition of satd aqNaHCO3. The precipitate was filtered through Celite pad and the padwas washed with CHCl3. The filtrate and washings were dried overNa2SO4, filtered, and concentrated. The resulting residue was exposedto high vacuum overnight. The residue was then dissolved in THF(120 mL). To the solution was added LiAlH4 (3.6 g, 96 mmol) at 0 C.After stirring for 45 min at rt, the completion of the reaction was confirmedby TLC (2:1 n-hexane/EtOAc). The reaction was quenched bythe addition of satd aq NH4Cl. The precipitate was filtered throughCelite pad and the pad was washed with EtOAc. The organic layer wassubsequently dried over Na2SO4, filtered, and concentrated, giving 43(8.0 g, 96%) as white powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; for 1h; | General procedure: To a solution of each sample (ca. 1.0 mg) in CCl4 (1.0 mL) was added NaIO4 (10 eq), RuCl3 (0.04 mg), CH3CN (1.0 mL), and H2O (1.0 mL). The solution was stirred vigorously for 1 h, then 1 M HCl (2.0 mL) was added and extracted with Et2O. Et2O layer was analyzed ESI-TOF-MS (negative ion) directly or methylated with TMS-CH2N2 in 20% MeOH/benzene followed by GC-MS analysis. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; for 1h; | General procedure: To a solution of each sample (ca. 1.0 mg) in CCl4 (1.0 mL) was added NaIO4 (10 eq), RuCl3 (0.04 mg), CH3CN (1.0 mL), and H2O (1.0 mL). The solution was stirred vigorously for 1 h, then 1 M HCl (2.0 mL) was added and extracted with Et2O. Et2O layer was analyzed ESI-TOF-MS (negative ion) directly or methylated with TMS-CH2N2 in 20% MeOH/benzene followed by GC-MS analysis. |
Tags: 505-52-2 synthesis path| 505-52-2 SDS| 505-52-2 COA| 505-52-2 purity| 505-52-2 application| 505-52-2 NMR| 505-52-2 COA| 505-52-2 structure
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