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Excepted Quantity | Free |
Inaccessible (Haz class 6.1), Domestic | USD 41.00 |
Inaccessible (Haz class 6.1), International | USD 64.00 |
Accessible (Haz class 3, 4, 5 or 8), Domestic | USD 83.00 |
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CAS No. : | 53774-20-2 | MDL No. : | MFCD00042650 |
Formula : | C5H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | N/A |
M.W : | 100.12 g/mol | Pubchem ID : | 143088 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 27.45 |
TPSA : | 37.3 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) : | -6.12 cm/s |
Log Po/w (iLOGP) : | 1.22 |
Log Po/w (XLOGP3) : | 1.11 |
Log Po/w (WLOGP) : | 0.89 |
Log Po/w (MLOGP) : | 0.79 |
Log Po/w (SILICOS-IT) : | 0.34 |
Consensus Log Po/w : | 0.87 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.03 |
Solubility : | 9.39 mg/ml ; 0.0938 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.49 |
Solubility : | 3.27 mg/ml ; 0.0326 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.06 |
Solubility : | 87.8 mg/ml ; 0.877 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.05 |
Signal Word: | Danger | Class: | 8 |
Precautionary Statements: | P210-P234-P260-P264-P280-P301+P330+P331+P310-P303+P361+P353+P310+P363-P304+P340+P310-P305+P351+P338+P310-P370+P378-P390-P403+P235-P405-P406-P501 | UN#: | 3265 |
Hazard Statements: | H227-H290-H314 | Packing Group: | Ⅱ |
GHS Pictogram: |
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* 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 pentane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl ether; magnesium |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pentane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | Stage #1: (E/Z)-crotyl bromide With lithium chloride; zinc In tetrahydrofuran for 2h; Stage #2: carbon dioxide With hydrogenchloride for 24h; | |
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction; | ||
Stage #1: (E/Z)-crotyl bromide; carbon dioxide With indium; cesium fluoride In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 2-chloro-3-butene With iodine; magnesium In tetrahydrofuran Inert atmosphere; Reflux; Stage #2: carbon dioxide In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; | |
(i) Mg, (ii) /BRN= 1900390/; Multistep reaction; | ||
With magnesium Multistep reaction; |
Stage #1: 2-chloro-3-butene With magnesium In tetrahydrofuran Heating; Stage #2: carbon dioxide In tetrahydrofuran at -78 - 10℃; Further stages.; | ||
19 %Spectr. | Stage #1: 2-chloro-3-butene; carbon dioxide With indium; lithium iodide In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
84% | With lithium aluminium tetrahydride | |
75% | With lithium aluminium tetrahydride In diethyl ether Heating; | |
With lithium aluminium tetrahydride |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With thionyl chloride | ||
With oxalyl dichloride at 0 - 20℃; for 57h; | ||
With oxalyl dichloride In chloroform at 0 - 20℃; for 3h; |
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 1h; | ||
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
18.5% | With (R)-1-phenyl-ethyl-amine In acetone Inert atmosphere; Reflux; | (S)-2-Methyl-3-butenoic acid ((S)-4; Method A) To a stirring solution of (±)-2-methyl-3-butenoic acid ((±)-4, 20.0 g, 0.200 mol) in acetone (200 mL) was added (R)-1-phenylethylamine (24.2 g, 0.200 mol) dropwise. The mixture washeated under reux to dissolve a precipitated salt. After coolingto room temperature, the precipitated salt was ltered. The resultingsalt was puried by recrystallization (1.0 g of salt/4.5 mLof acetone, twice). The obtained salt (9.07 g) was dissolved intodil. HCl (3 ; 90 mL), and the solution was extracted with Et2O.The organic layer was washed with brine, dried (Na2SO4) andconcentrated under reduced pressure to give (S)-4 (3.69 g, 18.5%yield): []D23 = +23.0 (c 1.50, CHCl3); NMR H (300 MHz, CDCl3):1.30 (3H, d, J = 7.2 Hz), 3.19 (1H, quint, J = 7.2 Hz), 5.14 (1H, dt,J = 10.2, 1.2 Hz), 5.18 (1H, dt, J = 17.1, 1.2 Hz), 5.93 (1H, ddd, J = 17.1,10.2, 7.2 Hz), 10.18 (1H, br); NMR C (125 MHz, CDCl3): 16.5, 43.5,116.6, 136.5, 181.2. The enantiomeric purity of (S)-4 was determinedby chiral GC analysis to be 54% e.e. Chiral GC: conditions:column, Chiramix (Tamogami et al. 2001) (0.25mmID × 30mL,0.25 μm df); temperature, 75 °C to 180 °C (0.7 °C/min); carrier N2(0.7 mL/min); tR (S)-4: 31.0 min (77.0%), (R)-4: 32.1 min (23.0%). |
With (-)-α-methylbenzylamine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 20℃; for 1h; Inert atmosphere; | |
82.9% | With lithium diisopropyl amide In tetrahydrofuran; hexane for 1h; Ambient temperature; | |
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - 24℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N-diethyl-N-isopropylamine; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 80℃; for 20h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With tetrafluoroboric acid In acetic acid for 1h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N,N-diethyl-N-isopropylamine; tetrabutyl-ammonium chloride In N,N-dimethyl-formamide at 80℃; for 20h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With bromine; sodium hydrogencarbonate at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 37% 2: 37% | With ammonium persulfate; trifluorormethanesulfonic acid at 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | at 120℃; for 14h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With isopropylmagnesium bromide In diethyl ether Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With magnesium 1.) -70 deg C, THF; 2.) -70 deg C, 0.5 h, then allowed to warm up to 0 deg C; Yield given. Multistep reaction; | ||
49 %Spectr. | Stage #1: carbon dioxide; 1-chloro-2-butene With indium; lithium iodide In N,N-dimethyl-formamide at 60℃; for 14h; Autoclave; Stage #2: With hydrogenchloride; water In ethyl acetate; N,N-dimethyl-formamide regioselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 28 % Spectr. 2: 72 % Spectr. | With tetraethylammonium perchlorate; magnesium In N,N-dimethyl-formamide at -10℃; electrochemical reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine In tetrahydrofuran at -78℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine In tetrahydrofuran at -78℃; for 1h; | ||
With 4-methyl-morpholine In tetrahydrofuran for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
51% | With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -75℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With bromine; triethylamine 1.) CH2Cl2, 1 h, 2.) CHCl3, reflux, 4 h; Yield given. Multistep reaction; | ||
Multi-step reaction with 2 steps 1: 42 percent / Br2, NaHCO3 / 0 °C 2: 59 percent / AgNO3 / acetic acid / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In tetrahydrofuran at -30℃; for 5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With water In diethyl ether Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With toluene-4-sulfonic acid In chloroform for 16h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With toluene-4-sulfonic acid In chloroform for 16h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | With methylaluminum dichloride In hexane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With methylaluminum dichloride In hexane at 20℃; for 3h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100 % Chromat. | With potassium phosphate buffer; Escherichia coli SS1001 cells In water at 35℃; for 1h; | |
With water at 35℃; for 1h; Enzymatic reaction; potassium phosphate buffer; | 18 EXAMPLE; 18 Hydrolysis of 2-Methyl-3-Butenitrile to 2-Methyl-3-Butenoic acid by E. coli SS1001 Cells A 5.0 mL suspension of 0.500 g (wet cell paste) E. COLI SS1001 cells (ATCC PTA-1177) in 50 mM potassium phosphate buffer (pH 7.0) was added to a mixture of 4.91 mL of 50 mM potassium phosphate buffer (PH 7.0) and 81.8 mg of 2-methyl-3-butenenitrile (101 mM final concentration), and the resulting suspension stirred at 35 C. Samples (0.100 mL) were mixed with 0.900 mL of 60 mM N-ethylacetamide (HPLC external standard) in 1: 1 ACETONITRILE : methanol, the resulting mixture was mixed, centrifuged, and the supernatant analyzed by HPLC for 2-METHYL- 3-butenenitrile and 2-methyl-3-butenoic acid. After 1 H, the conversion of 2-methyl-3-butenenitrile was 100 %, and 2-methyl-3-butenoic acid was the only product produced over the course of the reaction. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-Bromosuccinimide; diphenyl diselenide In acetonitrile at -30℃; for 5h; Title compound not separated from byproducts; | ||
With bromine; sodium hydrogencarbonate In diethyl ether |
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