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CAS No. : | 109232-37-3 | MDL No. : | MFCD03265308 |
Formula : | C11H21ClO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KPAZLWVDWUAYII-UHFFFAOYSA-N |
M.W : | 220.74 | Pubchem ID : | 13913710 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.91 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 60.81 |
TPSA : | 26.3 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) : | -5.08 cm/s |
Log Po/w (iLOGP) : | 2.98 |
Log Po/w (XLOGP3) : | 3.62 |
Log Po/w (WLOGP) : | 3.23 |
Log Po/w (MLOGP) : | 3.15 |
Log Po/w (SILICOS-IT) : | 3.29 |
Consensus Log Po/w : | 3.26 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.03 |
Solubility : | 0.207 mg/ml ; 0.000939 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.86 |
Solubility : | 0.0305 mg/ml ; 0.000138 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.46 |
Solubility : | 0.0769 mg/ml ; 0.000348 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.21 |
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 |
---|---|---|
43 kg (0.195 kg-mol, 94%) | EXAMPLE 2 Preparation of 2-Methylpropyl 5-Chloro-2,2-dimethylpentanoate (Commercial Scale) Employing, generally, the method of Example 1, 1.6 kg (0.230 kg-mol) of lithium metal was treated with 40.8 kg of dry tetrahydrofuran and 25.7 kg (0.254 kg-mol) of diisopropylamine followed by reaction with 12.68 kg (0.121 kg-mol) of styrene at temperatures between about 35-40 C. After reaction with the lithium metal was essentially complete, the mixture was cooled to temperatures between 5-15 C. and 30 kg (0.208 kg-mol) of 2-methylpropyl 2-methylpropanoate (isobutyl isobutyrate) was slowly added. The reaction mixture was again cooled to temperatures between about 5-15 C. and 42.5 kg (0.270 kg-mol) of 1-bromo-3-chloropropane was slowly added. After addition was complete, the mixture was allowed to warm to 14 C. over a period of about 13 hours. The final reaction mixture was quenched with 11.5 liters of water, the tetrahydrofuran removed, and the residue diluted with 75 liters of water and extracted with hexane. Removal of the hexane and distillation of the residue yielded 43 kg (0.195 kg-mol, 94%) of 2-methylpropyl 5-chloro-2,2-dimethylpentanoate, bp 94-98 C. at 4 Torr (0.53 kPascal). | |
With lithium dimethylamide; In hexane; at -20 - 0℃; for 8.0h;Inert atmosphere; | General procedure: The reaction flask was charged with 52g methyl isobutyrate (0.5mol)Dried n-hexane 300g,N2 gas protection,Cooled to -20 C,180 g (0.53 mol) of a 15% by weight solution of lithium dimethylamide in n-hexane was added dropwise at a controlled temperature of -10 C,Then control the temperature ?-10 dropwise 1,3-bromochloropropane 80g (0.51mol),After dropping at -5 or so for 3 hours,0 -10 then incubated for 5 hours,Dripped into water 50g, 15% hydrochloric acid to adjust pH to neutral, layered, washed with 50g water once, the solvent layer was recovered by atmospheric distillation solvent,The product was distilled off under reduced pressure to give 75 g of methyl 5-chloro-2,2-methylpentanoate. The GC content was 98% (area normalization), and the yield was 93.4%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With caesium carbonate; sodium iodide; In ISOPROPYLAMIDE; at 150℃; for 0.333333h;Microwave irradiation; | 5-iodo-N-methyl-6-(methylsulfonamido)-2-p-tolylfuro[2,3-b]pyridine-3-carboxamide (136 mg, 0.28 mmol) and <strong>[109232-37-3]isobutyl 5-chloro-2,2-dimethylpentanoate</strong> (124 mg, 0.56 mmol) are dissolved in DMA (1 mL) and Cs2C03 (183 mg, 0.56 mmol) and Nal (42 mg, 0.28 mmol) added. The mixture is microwaved at 150 C for 20 min then diluted with water and extracted with EtOAc (3 x20 mL). The organic is then washed with Brine (10 mL) and dried over Na2S04 and concentrated. HPLC purification gives 70 mg (38% yield) of alkylated product isobutyl 5-(N-(5-iodo-3-(methylcarbamoyl)-2-p-tolylfuro[2,3-b]pyridin-6- yl)methylsulfonamido)-2,2-dimethylpentanoate. MS-ES [M + H]+ = 670.2. This compound is used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | General procedure: A solution of phenol (5 mmol) was added to a solution of sodium (114 mg, 5 mmol) in absolute EtOH (5 mL) at room temperature. After stirring for 30 min, a solution of suitable ethyl or isobutyl ester (5-bromovalerate, 5-bromo-2,2-dimethylpentanoic acid ethyl ester or <strong>[109232-37-3]5-chloro-2,2-dimethylpentanoic acid isobutyl ester</strong>) (5 mmol) in absolute EtOH (5 mL) was added and the solution was stirred at reflux for 10-15 h. The solvent was removed under reduced pressure and the residue was dissolved into CH2Cl2 or ethyl acetate (25 mL) and washed with NaOH 2 N (3 × 25 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield the crude product that was purified by column chromatography to give the ester 9-14, 16 or 25-31. Ester 15 was obtained with the same procedure, but under milder conditions: K2CO3 (1.1 g, 8.38 mmol) was added to a solution of N-(4-hydroxyphenyl)-N'-phenylurea (531 mg, 2.33 mmol) in acetone (10 mL) at room temperature. After stirring for 30 min, a solution of ethyl 5-bromovalerate (488 mg, 2.33 mmol, 0.37 mL) in acetone (10 mL) was added. After 30 h the solvent was removed under reduced pressure and the residue was treated as above to give the compound 15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | General procedure: A solution of phenol (5 mmol) was added to a solution of sodium (114 mg, 5 mmol) in absolute EtOH (5 mL) at room temperature. After stirring for 30 min, a solution of suitable ethyl or isobutyl ester (5-bromovalerate, 5-bromo-2,2-dimethylpentanoic acid ethyl ester or <strong>[109232-37-3]5-chloro-2,2-dimethylpentanoic acid isobutyl ester</strong>) (5 mmol) in absolute EtOH (5 mL) was added and the solution was stirred at reflux for 10-15 h. The solvent was removed under reduced pressure and the residue was dissolved into CH2Cl2 or ethyl acetate (25 mL) and washed with NaOH 2 N (3 × 25 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield the crude product that was purified by column chromatography to give the ester 9-14, 16 or 25-31. Ester 15 was obtained with the same procedure, but under milder conditions: K2CO3 (1.1 g, 8.38 mmol) was added to a solution of N-(4-hydroxyphenyl)-N'-phenylurea (531 mg, 2.33 mmol) in acetone (10 mL) at room temperature. After stirring for 30 min, a solution of ethyl 5-bromovalerate (488 mg, 2.33 mmol, 0.37 mL) in acetone (10 mL) was added. After 30 h the solvent was removed under reduced pressure and the residue was treated as above to give the compound 15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | General procedure: A solution of phenol (5 mmol) was added to a solution of sodium (114 mg, 5 mmol) in absolute EtOH (5 mL) at room temperature. After stirring for 30 min, a solution of suitable ethyl or isobutyl ester (5-bromovalerate, 5-bromo-2,2-dimethylpentanoic acid ethyl ester or <strong>[109232-37-3]5-chloro-2,2-dimethylpentanoic acid isobutyl ester</strong>) (5 mmol) in absolute EtOH (5 mL) was added and the solution was stirred at reflux for 10-15 h. The solvent was removed under reduced pressure and the residue was dissolved into CH2Cl2 or ethyl acetate (25 mL) and washed with NaOH 2 N (3 × 25 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to yield the crude product that was purified by column chromatography to give the ester 9-14, 16 or 25-31. Ester 15 was obtained with the same procedure, but under milder conditions: K2CO3 (1.1 g, 8.38 mmol) was added to a solution of N-(4-hydroxyphenyl)-N'-phenylurea (531 mg, 2.33 mmol) in acetone (10 mL) at room temperature. After stirring for 30 min, a solution of ethyl 5-bromovalerate (488 mg, 2.33 mmol, 0.37 mL) in acetone (10 mL) was added. After 30 h the solvent was removed under reduced pressure and the residue was treated as above to give the compound 15. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.9 g | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; | Resveratrol 5.00g (21.91mmol) was dissolved in 30ml of anhydrous DMF, was added 9.0g (65.12mmol) of potassium carbonate and mix well. The 7.25g (32.81mmol) 5- chloro-2,2-dimethyl butyl isovalerate dissolved 20mL of anhydrous DMF, mixed evenly, an oil bath at 90 slowly dropped to the reaction system. Completion of the dropwise addition, heating was continued with stirring. The reaction was monitored by TLC. After completion of the reaction, the system was cooled to room temperature, potassium carbonate was removed by suction, the filter cake rinsed with ethyl acetate, collectedThe filtrate 50mL ethyl acetate added to the filtrate, after mixing, 2mol / LHCl washed 2 times 100mL, collect the organic phase, the aqueous stripping phase, the organic phases were combined, dried over anhydrous sodium sulfate. After completion of the drying, the solvent was evaporated under reduced pressure to give a brown oil which was chromatographed on a silica gel column (volume ratio 41) eluting with ethyl acetate petroleum ether , respectively, to give 3,5-dihydroxy-4 ' - (4-methyl-4-carboxy-pentyloxy) - (the E) - stilbene (iv-1) of a yellow solid 1.90g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.7 g | With potassium carbonate; In N,N-dimethyl-formamide; at 90℃; | The 1.65g (4.82mmol) compound i-2 was dissolved in 30ml of anhydrous DMF, was added 2.00g (14.47mmol) of potassium carbonate and mix well. The 1.06g (4.80mmol) 5- chloro-2,2-dimethyl butyl isovalerate dissolved 20mL of anhydrous DMF, mixed evenly, an oil bath at 90 condition slowly dropped to the reaction system. Completion of the dropwise addition, heating was continued with stirring. The reaction was monitored by TLC. After completion of the reaction, the system was cooled to room temperature, potassium carbonate was removed by suction, the filter cake rinsed with ethyl acetate, the filtrate was collected, 50mL of ethyl acetate was added to the filtrate, after mixing with 2mol / LHCl washed 2 times, each 100mL, organic phase was collected, stripping the aqueous phase, the organic phases were combined, dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to give a brown oil, brown oil was subjected to column chromatography eluting with petroleum ether separated ethyl acetate (volume ratio 41), desired fractions were collected to give3-hydroxy-5- (4-methyl-4-isobutyl-butyloxycarbonyl - pentyloxy) -4 '- (3-ethoxycarbonyl-propoxy) - (the E) - stilbene (iii- 1) yellow oil 0.70g. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 90℃; | Compound 1-1 (4-chloro-2,5-dimethylphenol) (780 mg, 5.0 mmol), <strong>[109232-37-3]5-chloro-2,2-dimethylvaleric acid isobutyl ester</strong> (1144 mg, 5.2 mmol), TBAI (36.9mg, 0.1mmol), potassium carbonate (1380mg, 10.0mmol) was dissolved in DMF (30mL), and stirred at 90 C overnight. TLC monitors the tendency of discontinuous conversion. The reaction solution is poured into water and the layers are separated. After the aqueous phase is extracted with ethyl acetate, the organic phases are combined, dried over anhydrous sodium sulfate, filtered and the filtrate is concentrated. Compound 1-2 (1.5 g) was isolated by analysis and the yield was 88%. |
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