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CAS No. : | 53774-20-2 | MDL No. : | MFCD00042650 |
Formula : | C5H8O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | GQWNPIKWYPQUPI-UHFFFAOYSA-N |
M.W : | 100.12 | 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 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With dilauryl peroxide In 1,2-dichloro-ethane Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
55% | Stage #1: trans-but-2-enyl chloride With iodine; magnesium In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; Reflux; Stage #2: carbon dioxide With sulfuric acid In tetrahydrofuran at -78℃; for 0.5h; | |
51% | Stage #1: trans-but-2-enyl chloride With magnesium In tetrahydrofuran for 3h; Heating; Stage #2: carbon dioxide In tetrahydrofuran Further stages.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With dmap; dicyclohexyl-carbodiimide at 20℃; for 12h; | |
98% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h; | 116.116B To a solution of 2-methylbut-3-enoic acid (2 g, 18.98 mmol) in CH2C12 (38.0 ml) was added phenylmethanol (1.966 ml, 18.98 mmol), DCC (3.92 g, 18.98 mmol) and DMAP (0.232 g, 1.898 mmol) (slight exotherm). The reaction was stirred at rt for four hours. The reaction was filtered off solid, rinsed with hexane, concentrated. Purification by normal phase chromatography gave 3.55 g (98%) of 116B as a colorless oil |
95% | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h; | 2.1 To a solution of 2-methylbut-3-enoic acid (1.0 g, 9.99 mmol) in dichloromethane (1 mL) was added benzyl alcohol (1.1 g, 9.99 mmol), N,N-dicyclohexylcarbodiimide (2.1 g, 9.99 mmol) and dimethylaminopyridine (122 mg, 1.00 mmol). After stirring at 20 °C for 16 hours, the reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 100 - 200 mesh, 0 - 5% ethyl acetate in petroleum ether) to afford benzyl 2-methylbut-3-enoate (1.8 g, 95%) as colorless oil. |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; Inert atmosphere; | ||
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | Intermediate 13. Benzyl 2-methylbut-3-enoate: To a solution of 2-methylbut- 3-enoic acid (9.5 g, 95 mmol) in DCM (80 mL) was added phenylmethanol (10.26 g, 95 mmol), N^-methanediylidenedicyclohexanamine (19.58 g, 95 mmol) and DMAP (1.159 g, 9.49 mmol) (exothermic reaction) and the resulting mixture was stirred at rt over weekend. The reaction mixture was filtered through a pad of CELITE to remove the solids and the filtrate was collected and concentrated. The filtrate was then concentrated and subjected to silica gel chromatography to yield the desired product as colorless oil. | |
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | [00354] Intermediate 17. Benzyl 2-methylbut-3-enoate: To a solution of 2-methylbut- 3-enoic acid (9.5 g, 95 mmol) in DCM (80 mL) was added phenylmethanol (10.26 g, 95 mmol), N^-methanediylidenedicyclohexanamine (19.58 g, 95 mmol) and DMAP (1.159 g, 9.49 mmol) (exothermic reaction) and the reaction was stirred at rt over weekend. The reaction mixture was filtered through a pad of CELITE to remove the solids and the filtrate was concentrated. The residue was purified by silica gel chromatography to yield the desired product as a colorless oil. | |
186.2 mg | With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; Cooling with ice; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 3: 96 percent / 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 4-methylmorpholine / tetrahydrofuran / 0.08 h 2: 0.69 g / n-BuLi / tetrahydrofuran; hexane / 0.17 h / 0 °C 3: 12 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 72 percent / p-TsOH / CHCl3 / 16 h / Heating 2: 75 percent / Ti(OiPr)4 / RuCl2(=CHPh)(PCy3)(1,3-Mes-2-imidazolidin-2-yl) / 7.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 75 percent / p-TsOH / CHCl3 / 16 h / Heating 2: 83 percent / Ti(OiPr)4 / RuCl2(=CHPh)(PCy3)(1,3-Mes-2-imidazolidin-2-yl) / 7.5 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h | ||
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h | ||
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h | ||
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h | ||
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h |
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h | ||
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h | ||
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h |
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) N-methylmorpholine / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h | ||
Multi-step reaction with 2 steps 1: Et3N / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 1 h, b) from -78 deg C to RT, 4 h | ||
Multi-step reaction with 2 steps 1: N-methylmorpholine / tetrahydrofuran / 1 h / -78 °C 2: 1.) n-BuLi, 2.) Et3N / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 1 h, b) RT, 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: oxalyl chloride / 57 h / 0 - 20 °C 2: NH2OH*HCl, KOH / tetrahydrofuran; methanol / 2.25 h / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: oxalyl chloride / 57 h / 0 - 20 °C 2: NH2OH*HCl, KOH / tetrahydrofuran; methanol / 2.25 h / 0 - 20 °C 3: pyridine / tetrahydrofuran / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) AgBF4, 2) aq. Na2CO3 / 1) CH2Cl2, -60 deg C, then rt, overnight, 2) CH2Cl2, 3 h, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) AgBF4, 2) aq. Na2CO3 / 1) CH2Cl2, -60 deg C, then rt, overnight, 2) CH2Cl2, 3 h, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) ZnCl2, 2) aq. Na2CO3 / 1) CH2Cl2, rt, overnight, 2) CH2Cl2, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 75 percent / LiAlH4 / diethyl ether / Heating 2: 1) NaH / 1) DME, reflux, overnight, 2) reflux, 24 h 3: 1) ZnCl2, 2) aq. Na2CO3 / 1) CH2Cl2, rt, overnight, 2) CH2Cl2, reflux 4: hydrazine hydrate / ethanol / 2 h / Heating 5: t-BuOK / dimethylsulfoxide / Ambient temperature 6: H2 / Raney nickel / ethanol / 60 h / 2250.2 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 79 percent / CCl4 / 120 h / 30 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 24 percent / CCl4 / 35 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: Ph3P-Br2-Et3N 3: 45 percent / CCl4 / 35 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: SOCl2 2: diethyl ether 3: LiAlH4 / diethyl ether 4: H2 / Pd-CaCO3 / methanol / 760 Torr |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1 2M3BA=2-Methyl-3-butenoic acid 2M3BA=2-Methyl-3-butenoic acid CrX=Mixture of Crotyl acetate, 3-Acetoxybutene-1, 3-Iodobutene-1, cis- and trans-crotyl iodides 3PA=cis+trans-3-pentenoic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
4.1% | 1 Example 1 After 1 hour the butadiene (BD) conversion was 78.3%, the yield of cis- and trans-3-pentenoic acid (3PA) was 90.9%, the yield of 2-methyl-3-butenoic acid (2M3BA) was 4.2% and the yield of valerolactone (VL) was 5.0%. After 5 hours the BD conversion was 98.2%, the yield of 3PA was 74%, the yield of 2M3BA was 4.1% and the yield of valerolactone was 15.6%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3.2% | 2 Example 2 After 1 hour the butadiene conversion was 52.3% and the 3PA yield was 92.1%, the yield of 2M3BA was 3.2% and the yield of VL was 0.9%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With Hoveyda-Grubbs catalyst second generation; p-benzoquinone In dichloromethane Reflux; Inert atmosphere; | |
In dichloromethane for 24h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With hydrogenchloride; air; carbon dioxide In diethyl ether Addn. of n-PrMgBr (Et2O) to stirred Et2O suspn. of Cp2TiCl2 and C4H6 (Ar, 0°C) over 5 min, stirring (30 min) at room temp. Bubbling of CO2 through soln. (1 h, room temp.), hydrolysis with aq. HCl, passing of air into react. mixt. for 15 min.; Filtn. gives Cp2TiCl2 in 93% yield recovery. Addn. of aq. NaOH to filtrate, sepn. of org. layer, discarding; extn. of aq. layer with ether, discarding, addn. of concd. HCl, extn. with ether, drying, concn. in vac. Purifn. by trap-to-trap distn.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 85% 2: 82% | With hydrogenchloride; air; carbon dioxide In diethyl ether Passing of gaseous CO2 through Et2O soln. of Ti-compd. (Ar) for 1 h, hydrolysis with aq. HCl and then bubbling of air into react. mixt. for 15 min.; Collecting of pptd. crystals of Cp2TiCl2 by filtn., addn. of aq. NaOH, sepn. of org. layer and discarding. Extn. of aq. layer with ether, discarding, addn. of concd. HCl, extn. with ether, drying, concn. in vac. Purifn. by trap-to-trap distn., (1)H NMR.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With sodium hydroxide; dihydrogen peroxide In methanol; water at 20℃; for 0.0833333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; trifluoro-[1,3,5]triazine In dichloromethane at 0℃; for 2h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With Hoveyda-Grubbs catalyst second generation In dichloromethane for 72h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
47% | With Hoveyda-Grubbs catalyst second generation In dichloromethane for 72h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In N,N-dimethyl-formamide; toluene at 20℃; for 39h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide; toluene Cooling; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
3% | Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In tetrahydrofuran; toluene at 20℃; for 40h; Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene Cooling; | |
3% | Stage #1: carbon dioxide; buta-1,3-diene With triethylaluminum In N,N-dimethyl-formamide; toluene at 20℃; for 72h; Stage #2: With hydrogenchloride In water; N,N-dimethyl-formamide; toluene Cooling; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C | ||
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C | ||
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.5 h / -78 °C 2.1: hydrogenchloride / tetrahydrofuran; water; chloroform / 0 °C / pH 3 |
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 1.58 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C | ||
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 0.5 h / 0 °C | ||
Stage #1: 2-methylbut-3-enoic acid With (<i>S</i>)-1-phenyl-ethylamine In acetone at 80℃; for 0.666667h; Stage #2: With hydrogenchloride In water at 20 - 30℃; for 0.666667h; | B.2; B.3 Step 2 : Preparation of (R)-2-methylbut-3-enoic acid (S)-1-phenyl-ethane salt (SM-2-4) Compound SM-2-2 (48g, 48mmol) was dissolved in acetone (100 mL) was added Compound SM-2-3 (67mL, 52mmol), refluxed for 40min 80C , natural cooling after crystallization.After suction filtration, the filter cake was added 50mL of acetone, dissolved by heating, crystallization at room temperature, suction-filtered to give the target molecule SM-2-4 (20.5g, 19%, dr≈2/1).Compound SM-2-4 (22g, 99mmol) was dissolved in 1N hydrochloric acid solution (135mL) was stirred at rt 40min, after-treatment to give SM-2 (9.8g, 98%) | |
Multi-step reaction with 2 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 4 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux | ||
Multi-step reaction with 4 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C 3.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / 40 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1.1: pivaloyl chloride; 4-methyl-morpholine / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2.58 h / -78 °C 2.1: lithium hydroxide; dihydrogen peroxide / tetrahydrofuran; water / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: palladium 10% on activated carbon; hydrogen / methanol / 20 h / 2585.81 Torr / Inert atmosphere | ||
Multi-step reaction with 5 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / -78 - 0 °C 1.2: 2 h / -78 °C 2.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / 0.5 h / 0 °C 3.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; pyridine / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid / dichloromethane / 1 h / Inert atmosphere; Reflux 4.2: 4 h / Inert atmosphere; Reflux 5.1: hydrogen; palladium 10% on activated carbon / methanol / 20 h / 2585.81 Torr / Inert atmosphere | ||
Multi-step reaction with 5 steps 1.1: 4-methyl-morpholine; pivaloyl chloride / tetrahydrofuran / 2 h / -78 - 0 °C 1.2: 2 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; water / 1.25 h / -1.5 - 1 °C 3.1: pyridine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide / ethyl acetate / -10 - 20 °C 4.1: toluene-4-sulfonic acid; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 5 h / 40 °C / Inert atmosphere 5.1: hydrogen; palladium 10% on activated carbon / methanol; tetrahydrofuran / 22 h / 20 °C / 2844.39 Torr |
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