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The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
4-Penten-1-ol is a low-toxicity, biodegradable alcohol compound widely used as a flavor component in food, beverages, and perfumes. It can also serve as a starting material for the synthesis of organic compounds and has antimicrobial properties.
Synonyms: Pent-4-en-1-ol
4.5
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Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
CAS No. : | 821-09-0 |
Formula : | C5H10O |
M.W : | 86.13 |
SMILES Code : | C=CCCCO |
Synonyms : |
Pent-4-en-1-ol
|
MDL No. : | MFCD00002975 |
InChI Key : | LQAVWYMTUMSFBE-UHFFFAOYSA-N |
Pubchem ID : | 13181 |
GHS Pictogram: |
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Signal Word: | Danger |
Hazard Statements: | H225 |
Precautionary Statements: | P210-P403+P235 |
Class: | 3 |
UN#: | 1987 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
95.22% | With pyridine; thionyl chloride; bismuth(III) oxide; at 0 - 30℃; for 72h; | In a 2000 ml four-necked flask equipped with a mechanical stirrer, a dropping funnel, a reflux condenser and a thermometer,200 g (2.33 mol) of 4-penten-1-ol, 2 g of bismuth trioxide and 700 g of pyridine were added.The temperature of the system was lowered to 0 C with ice-salt bath with stirring. At this point, 238 g (2 mol) of thionyl chloride was added dropwise to the system with a dropping funnel.Control the rate of dropping to ensure that the material temperature does not exceed 5 , dropping the end, remove the ice salt bath. Naturally heated to between 10-30 , the reaction was stirred for 72 hours.When the temperature exceeds 30 , use ice salt bath to cool below 30 . After the reaction was completed, the mixture was filtered through a Buchner funnel and the filter cake was taken as a catalyst and pyridine hydrochloride. The filter cake was rinsed twice with 200 ml of acetone.The combined filtrate and washings, poured into 1500ml of distilled water, allowed to stand, separate the lower reservoir.The oil layer was further washed with distilled water to neutrality, and then distilled under reduced pressure in a water pump to collect the distillate fraction (vacuum 255 mmHg) at a head temperature of 88-95 C.199g colorless liquid was obtained in a yield of 95.22%. Gas chromatography detection of content of 98.27%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.1.6 1-Methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylic acid 10b A solution of pent-4-en-1-ol (1.45?mL, 14.0?mmol) in THF (24.0?mL) was cooled to -8?C and treated with 1.0?M sodium hexamethyldisilazane in THF (14.0?mL, 14.0?mmol). The reaction mixture was stirred at the reduced temperature for 5?min before the ice bath was removed. Stirring was continued for an additional 25?min before being treated with a solution of <strong>[105486-72-4]ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate</strong> (1.1?g, 4.7?mmol) in THF (24?mL). The reaction mixture was stirred for 1 hour at room temperature before being quenched with 50?mL of sat. NH4Cl. The crude product was extracted with DCM (60?mL x 3), dried with Na2SO4 and concentrated under reduced pressure. This material purified by SiO2 chromatography (ethyl acetate: petroleum ether?=?1:5) to afford 0.65?g impure product 9b mixed with pent-4-en-1-yl 1-methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylate (produced through transesterification reaction), the mixed esters could both be the raw materials for next hydrolysis, so the mixture was put into next step without further separation. To a solution of the mixed esters in 5?mL MeOH/THF (VMeOH:VTHF?=?1:1) at 0? was added 5?mL 2M NaOH (aq). The mixture was stirred at room temperature for 3?h and MeOH and THF were evaporated in vacuo. The residue was acidified to pH?=?2-3 with 1?N HCl and extracted with ethyl acetate (10?mL?*?3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford compound 10b as yellow solid (0.45?g, 46%). 1 H NMR (500?MHz, CDCl3) delta 7.84 (s, 1H), 5.89-5.77 (m, 1H), 5.10-5.00 (m, 2H), 4.46 (t, J?=?6.5?Hz, 2H), 3.70 (s, 4H), 2.28-2.19 (m, 2H), 1.93-1.85 (m, 2H); ESI-MS: m/z?=?209 [M-H]-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
46% | A solution of pent-4-en-1-ol (1.45?mL, 14.0?mmol) in THF (24.0?mL) was cooled to -8?C and treated with 1.0?M sodium hexamethyldisilazane in THF (14.0?mL, 14.0?mmol). The reaction mixture was stirred at the reduced temperature for 5?min before the ice bath was removed. Stirring was continued for an additional 25?min before being treated with a solution of <strong>[105486-72-4]ethyl 5-bromo-1-methyl-1H-pyrazole-4-carboxylate</strong> (1.1?g, 4.7?mmol) in THF (24?mL). The reaction mixture was stirred for 1 hour at room temperature before being quenched with 50?mL of sat. NH4Cl. The crude product was extracted with DCM (60?mL x 3), dried with Na2SO4 and concentrated under reduced pressure. This material purified by SiO2 chromatography (ethyl acetate: petroleum ether?=?1:5) to afford 0.65?g impure product 9b mixed with pent-4-en-1-yl 1-methyl-5-(pent-4-en-1-yloxy)-1H-pyrazole-4-carboxylate (produced through transesterification reaction), the mixed esters could both be the raw materials for next hydrolysis, so the mixture was put into next step without further separation. To a solution of the mixed esters in 5?mL MeOH/THF (VMeOH:VTHF?=?1:1) at 0? was added 5?mL 2M NaOH (aq). The mixture was stirred at room temperature for 3?h and MeOH and THF were evaporated in vacuo. The residue was acidified to pH?=?2-3 with 1?N HCl and extracted with ethyl acetate (10?mL?*?3). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to afford compound 10b as yellow solid (0.45?g, 46%). 1 H NMR (500?MHz, CDCl3) delta 7.84 (s, 1H), 5.89-5.77 (m, 1H), 5.10-5.00 (m, 2H), 4.46 (t, J?=?6.5?Hz, 2H), 3.70 (s, 4H), 2.28-2.19 (m, 2H), 1.93-1.85 (m, 2H); ESI-MS: m/z?=?209 [M-H]-. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With rhodium(III) chloride trihydrate; copper diacetate; In N,N-dimethyl-formamide; at 90℃; under 760.051 Torr; for 10h;Sealed tube; | AddN-pyrimidinylpurine 1a (0.2 mmol), RhCl3•3H2O (0.004 mmol), Cu(OAc)2(0.4 mmol) andpent-4-en-1-ol 2l (1.0 mmol) to 2.0 In mL of DMF, after replacing carbon monoxide three times in Young's tube,add carbon monoxide (1 atm), react with 90 C oil bath for 10 hours, stop the reaction, wait until the reaction solution is cooled to room temperature, addethyl acetate and saturate The saline is washed and extracted several times.The organic phase was dried over anhydrous sodium sulfate and filtered.The solvent was evaporated to dryness, andethyl acetate / petroleum ether (1:10 to 1:1) was obtained.The product was a colorless oily liquidwith a yield of 65%. |