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[ CAS No. 53774-20-2 ]

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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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3d Animation Molecule Structure of 53774-20-2
Chemical Structure| 53774-20-2
Chemical Structure| 53774-20-2
Structure of 53774-20-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 53774-20-2 ]

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 :

Calculated chemistry of of [ 53774-20-2 ]

Physicochemical Properties

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

Pharmacokinetics

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

Lipophilicity

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

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

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

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.05

Safety of [ 53774-20-2 ]

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:
GHS Pictogram:

Application In Synthesis of [ 53774-20-2 ]

* 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.

  • Downstream synthetic route of [ 53774-20-2 ]

[ 53774-20-2 ] Synthesis Path-Downstream   1~31

  • 1
  • [ 106-98-9 ]
  • [ 1822-71-5 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With pentane
  • 2
  • (E/Z)-crotyl bromide [ No CAS ]
  • [ 22037-73-6 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With diethyl ether; magnesium
  • 3
  • [ 107-01-7 ]
  • [ 1822-71-5 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
With pentane
  • 4
  • (E/Z)-crotyl bromide [ No CAS ]
  • [ 124-38-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation 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;
  • 5
  • [ 563-52-0 ]
  • [ 124-38-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation 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;

  • 6
  • [ 53774-20-2 ]
  • [ 4516-90-9 ]
YieldReaction ConditionsOperation in experiment
84% With lithium aluminium tetrahydride
75% With lithium aluminium tetrahydride In diethyl ether Heating;
With lithium aluminium tetrahydride
  • 7
  • [ 53774-20-2 ]
  • [ 24560-24-5 ]
YieldReaction ConditionsOperation 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;

  • 8
  • [ 53774-20-2 ]
  • [ 59014-11-8 ]
YieldReaction ConditionsOperation 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
  • 9
  • [ 80-59-1 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation 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;
  • 10
  • [ 53774-20-2 ]
  • [ 16644-98-7 ]
  • (3S,5S)-5-((E)-Hex-1-enyl)-3-methyl-dihydro-furan-2-one [ No CAS ]
  • (3R,5S)-5-((E)-Hex-1-enyl)-3-methyl-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 11
  • [ 53774-20-2 ]
  • [ 3240-34-4 ]
  • dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With tetrafluoroboric acid In acetic acid for 1h; Ambient temperature;
  • 12
  • [ 53774-20-2 ]
  • [ 588-72-7 ]
  • (3S,5S)-3-Methyl-5-((E)-styryl)-dihydro-furan-2-one [ No CAS ]
  • (3R,5S)-3-Methyl-5-((E)-styryl)-dihydro-furan-2-one [ No CAS ]
YieldReaction ConditionsOperation 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;
  • 13
  • [ 53774-20-2 ]
  • 4-Bromomethyl-3-methyl-oxetan-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With bromine; sodium hydrogencarbonate at 0℃;
  • 14
  • [ 53774-20-2 ]
  • [ 64-19-7 ]
  • cis-dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
  • trans-dihydro-3-methyl-4-acetoxy-2(3H)-furanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
1: 37% 2: 37% With ammonium persulfate; trifluorormethanesulfonic acid at 70℃;
  • 15
  • [ 53774-20-2 ]
  • [ 106-99-0 ]
  • (3E,6E)-2-Methyl-octa-3,6-dienoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
68% at 120℃; for 14h;
  • 16
  • [ 124-38-9 ]
  • [ 106-99-0 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
70% With isopropylmagnesium bromide In diethyl ether Ambient temperature;
  • 17
  • [ 124-38-9 ]
  • [ 591-97-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation 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;
  • 18
  • (E)-1-Bromo-2-butene [ No CAS ]
  • [ 124-38-9 ]
  • [ 1617-32-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
1: 28 % Spectr. 2: 72 % Spectr. With tetraethylammonium perchlorate; magnesium In N,N-dimethyl-formamide at -10℃; electrochemical reaction;
  • 19
  • [ 53774-20-2 ]
  • [ 3282-30-2 ]
  • C10H16O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine In tetrahydrofuran at -78℃; for 1h;
  • 20
  • [ 53774-20-2 ]
  • [ 543-27-1 ]
  • C10H16O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With 4-methyl-morpholine In tetrahydrofuran at -78℃; for 1h;
With 4-methyl-morpholine In tetrahydrofuran for 0.0833333h;
  • 21
  • [ 75-77-4 ]
  • [ 53774-20-2 ]
  • (E)-2-Methyl-4-trimethylsilanyl-but-2-enoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
51% With n-butyllithium; potassium <i>tert</i>-butylate In tetrahydrofuran; hexane at -75℃;
  • 22
  • [ 53774-20-2 ]
  • [ 22122-36-7 ]
YieldReaction ConditionsOperation 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
  • 23
  • [ 80-59-1 ]
  • [ 591-51-5 ]
  • [ 53774-20-2 ]
  • [ 19731-91-0 ]
YieldReaction ConditionsOperation in experiment
43% In tetrahydrofuran at -30℃; for 5h;
YieldReaction ConditionsOperation in experiment
68% With water In diethyl ether Ambient temperature;
  • 25
  • [ 53774-20-2 ]
  • [ 107-18-6 ]
  • 2-methyl-but-3-enoic acid allyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
75% With toluene-4-sulfonic acid In chloroform for 16h; Heating;
  • 26
  • [ 53774-20-2 ]
  • [ 513-42-8 ]
  • 2-methyl-but-3-enoic acid 2-methyl-allyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With toluene-4-sulfonic acid In chloroform for 16h; Heating;
  • 27
  • [ 124-38-9 ]
  • [ 17486-12-3 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
42% With methylaluminum dichloride In hexane at 20℃; for 3h;
  • 28
  • [ 124-38-9 ]
  • [ 34584-84-4 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation in experiment
43% With methylaluminum dichloride In hexane at 20℃; for 3h;
  • 29
  • [ 16529-56-9 ]
  • [ 53774-20-2 ]
YieldReaction ConditionsOperation 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.
  • 30
  • [ 53774-20-2 ]
  • [ 125763-07-7 ]
  • (3R,4R)-4-Bromomethyl-3-methyl-oxetan-2-one [ No CAS ]
YieldReaction ConditionsOperation 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
  • 31
  • acetic acid 1-ethoxythiocarbonylsulfanyl-3-methyl-butyl ester [ No CAS ]
  • [ 53774-20-2 ]
  • 5-acetoxy-3-ethoxythiocarbonylsulfanyl-2,7-dimethyl-octanoic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With dilauryl peroxide In 1,2-dichloro-ethane Heating;
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