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CAS No. : | 15026-17-2 | MDL No. : | MFCD00273441 |
Formula : | C8H14O4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PCOCFIOYWNCGBM-UHFFFAOYSA-N |
M.W : | 174.19 | Pubchem ID : | 4139107 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.75 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 43.66 |
TPSA : | 63.6 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) : | -6.99 cm/s |
Log Po/w (iLOGP) : | 1.72 |
Log Po/w (XLOGP3) : | 0.53 |
Log Po/w (WLOGP) : | 1.19 |
Log Po/w (MLOGP) : | 0.93 |
Log Po/w (SILICOS-IT) : | 0.7 |
Consensus Log Po/w : | 1.01 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.92 |
Solubility : | 20.8 mg/ml ; 0.119 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.44 |
Solubility : | 6.37 mg/ml ; 0.0366 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.96 |
Solubility : | 19.1 mg/ml ; 0.11 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.96 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501 | 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 |
---|---|---|
100% | With dmap; 1-hydroxy-pyrrolidine-2,5-dione In toluene for 48 h; Reflux | The monoester of succinate was prepared as described by Srinivasan,Uttamchandani and Yao [42]: Tert-butanol (10 mL) was added to asolution of succinic anhydrate (6.04 g, 60.40 mmol), Nhydroxysuccinimid (2.53g, 22.01 mmol) and DMAP (0.88 g, 7.23 mmol) in toluene (100 mL)and the solution was heated for 48 h under reflux conditions. After cooling down to rt, twolayers formed in the reaction vessel (brown oil and clear, colourless solution). The crudesolution was diluted with EtOAc (50 mL) and washed with citric acid (10 percent, 2 × 50 mL) andbrine. The organic layer was dried over Na2SO4, the solvent evaporated and the crude productwas recrystallized from Et2O/PE (1:3, 25 mL) to yield the title compound in quantitativeyield. |
77% | With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine In toluene for 24 h; Inert atmosphere; Reflux | Succinic anhydride 7 (10 g, 100 mmol), N-hydroxysuccinimide (3.34 g, 0.30 mmol), and DMAP (1.17 g, 1.00 mmol) were dissolved in toluene (50 mL). tert-Butanol (11.7 mL, 124 mmol) and Et3N (3.03 g, 4.17 mL, 30.0 mmol) were added sequentially. The suspension was heated under reflux for 24 h. The solution was cooled and diluted with EtOAc (50 mL) and was washed with citric acid (10percent w/v, 100 mL) and brine (100 mL), dried over Na2SO4, and concentrated to give a brown solid. The solid was recrystallised with ether and petroleum ether (10:90) at -20 °C to give succinic acid mono-tert-butyl ester 8 (13.3 g, 76.4 mmol, 77percent) as fawn crystals |
77% | With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine In toluene | Succinic anhydride (10 g, 100 mmol) was reacted with anhydrous t-butyl alcohol (17 mL) in anhydrous toluene (150 mL) in the presence of dimethylaminopyridine (1.8 g, 15 mmol), N-hydroxysuccinamide (3.45 g, 30 mmol), and trimethylamine (4.2 mL, 30 mmol) to yield the ring opened mono-tert-butylsuccinate product (4). The product was purified by ethyl acetate and water extractions followed by recrystallization of the isolated products of the organic phase in 1:3 ether:hexanes (77percent). The pure compound (4) (5.57 g, 31.9 mmol) was then reacted with tert-Butyldimethylchlorosilane (TBDMS) protected diethanolamine (24.6 mmol) in a 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) (6.60 g, 34.4 mmol) mediated coupling reaction in anhydrous N,N-dimethylformamide (DMF) (30 mL) overnight. The resulting product (5) was purified by removing the DMF via rotovap, performing ethyl acetate and water extractions, and further purifying the product by performing silica gel liquid column chromatography using ethyl acetate and hexanes as the mobile phase (69.8percent). Deprotection of the TBDMS groups was performed by reacting the purified product from the previous step with iodine in methanol (2percent w/v) at reflux for three hours. After reaction, Na2S2O3 was added until the reaction mixture became clear and was concentrated on rotary evaporator. To purify the t-butyl protected carboxylate diol monomer (5), methylene chloride and water extractions were performed followed by silica gel liquid column chromatography using methylene chloride and methanol as the mobile phase to purify the products extracted into the organic phase. The product was dried under reduced pressure to yield pure monomer (6) (61percent). Synthesis of the monomer was confirmed by 1HNMR. |
64% | With dmap; 1-hydroxy-pyrrolidine-2,5-dione; triethylamine In toluene for 24 h; Inert atmosphere; Reflux | Succinic anhydride, 3 (5.0g, 49.96mmol) was suspended in 30mL of toluene under nitrogen atmosphere. N-Hydroxysuccinimide (1.72g, 14.98mmol), 4-(dimethylamino)pyridine (0.610g, 4.9mmol), dry tert-butyl alcohol (15mL, 150mmol), and Et3N (2.10mL, 14.98mmol) were added to the solution. Dissolution occurred upon refluxing it for one day. After cooling, ethyl acetate (20mL) was added, and the organic layer was washed three times with 10percent citric acid and once with brine, and dried over Na2SO4, filtered, and evaporated to afford 5.40g (64percent yield) of brown solid. Recrystallization with ether gave white crystals of 4. The structure was confirmed by 1H NMR. Mp: 49–50°C (lit.22 49–51°C) 1H NMR (500MHz, CDCl3) δ 2.61 (t, J=6.7Hz, 2H), 2.56–2.49 (m, 2H), 1.43 (s, 9H); 13C NMR (125MHz, CDCl3) 178.7, 171.6, 81.2, 30.2, 29.3, 28.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With palladium 10% on activated carbon; hydrogen In tetrahydrofuran for 16 h; | To a stirred solution of benzyl tert-butyl butanedioate (2.3 g, 8.71 mmol) in dry THF (30mL), 10percent Pd-C (0.23 g) was added and stirred under H2 atmosphere (balloon) for 16 h (TLCindicated complete consumption of starting material). The reaction mixture was filteredthrough Celite and washed with CHCh (100 mL). The filtrate was concentrated in vacuo togive crude residue which was purified by column chromatography (100-200 silica gel, 30 g,35percent EtOAc-Hexane) to afford 4-tert-butoxy-4-oxo-butanoic acid (0.8 g, 52percent) as a colorlessoil.1H NMR [400 MHz, CDCh]: 8 2.65-2.61 (m, 2H), 2.56-2.52 (m, 2H), 1.44 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; for 24 h; Inert atmosphere | BH3.Me2S (2.0 M in THF, 6.6 mL, 13.1 mmol) was added dropwise to a solution of carboxylic acid 8 (2.12 g, 12.2 mmol) in dry THF (20 mL) cooled to 0° C. The solution was allowed to warm to room temperature and stirred for 24 h. EtOAc (100 mL) was added and the organic layer separated and washed with water (70 mL) and brine (70 mL), dried over MgSO4, filtered and the solvent removed under reduced pressure to give tert-butyl 4-hydroxybutanoate 9 (1.92 g, 12.2 mmol, quant.), which was used without any further purification as a pale yellow oil |
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