6-oxo-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; water at 0℃; for 1h; Inert atmosphere; | 98% |
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 2h; | 72% |
With trifluoroacetic acid In dichloromethane at 20℃; Inert atmosphere; |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran at 0 - 20℃; for 2h; | 97.7% |
In tetrahydrofuran at 0 - 20℃; for 2h; | 0.55 g |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 2h; Reflux; | 94% |
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 2h; | 56% |
3-(phenylthio)piperidin-2-one
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Stage #1: 3-(phenylthio)piperidin-2-one With sodium hydrogencarbonate In dichloromethane for 0.166667h; Stage #2: With 3-chloro-benzenecarboperoxoic acid for 1h; Further stages.; | 90% |
Stage #1: 3-(phenylthio)piperidin-2-one With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 2h; Stage #2: In toluene for 1h; Reflux; | 80% |
Multi-step reaction with 2 steps 1: m-CPBA, aq.NaHCO3 / CH2Cl2 / 1 h / 0 °C 2: 1.17 g / benzene / 1 h / Heating View Scheme |
N-(but-3-en-1-yl)prop-2-enamide
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In toluene at 85 - 90℃; for 7h; | 75% |
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 6h; Grubbs Olefin Metathesis; Reflux; | 70% |
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane for 6h; Reflux; | 70% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
at 260℃; under 1 Torr; | 68% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With lithium hydroxide monohydrate In tetrahydrofuran at 50℃; for 4h; | 68% |
(E)-2,4-pentadienoic acid
A
5,6-dihydro-2(1H)-pyridinone
B
1,6-dihydropyridin-2(3H)-one
Conditions | Yield |
---|---|
With ammonia Yield given. Yields of byproduct given; |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
In benzene for 1h; Heating; | 1.17 g |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran 1.) 0 deg C, 30 min, 2.) 25 deg C, 1.5 h; Yield given; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LDA / tetrahydrofuran; hexane / 1.) -50 deg C, 45 min, 2.) -78 deg C, 7 h 2: 50percent H2O2 / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) 25 deg C, 1.5 h View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 0.75 h / -50 °C / Inert atmosphere 1.2: 7 h / -78 °C / Inert atmosphere 2.1: dihydrogen peroxide / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme |
1-(methoxymethyl)-3-(phenylthio)piperidin-2-one
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 78 percent / conc.HCl / ethanol / 6 h / Heating 2: m-CPBA, aq.NaHCO3 / CH2Cl2 / 1 h / 0 °C 3: 1.17 g / benzene / 1 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1.1: hydrogenchloride / ethanol; water / 6 h / Reflux 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C 2.2: 1 h / Reflux View Scheme |
A
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With 4-methyl-morpholine In 1,4-dioxane at 80℃; for 18h; | A 6 mg B 36 mg |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride Grubbs Olefin Metathesis; |
2-oxopiperidine-1-carboxylic acid tert-butyl ester
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.5 h / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 2.2: 3 h / 80 °C / Inert atmosphere 3.1: hydrogenchloride / methanol; water / 1 h / 0 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 4 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 1.5 h / -78 °C / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 2 h / 0 °C 3.1: toluene / 3 h / 80 °C 4.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C View Scheme |
N-(tert-butyloxycarbonyl)-3-(phenylthio)piperidine-2-one
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 1.2: 3 h / 80 °C / Inert atmosphere 2.1: hydrogenchloride / methanol; water / 1 h / 0 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 2 h / 0 °C 2: toluene / 3 h / 80 °C 3: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 1.2: 16 h / 20 °C / Inert atmosphere 2.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere 2.2: 1.5 h / Inert atmosphere 3.1: 3-chloro-benzenecarboperoxoic acid; sodium hydrogencarbonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere 3.2: 3 h / 80 °C / Inert atmosphere 4.1: hydrogenchloride / methanol; water / 1 h / 0 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 13 h / 0 - 20 °C 2: 2,5-di-tert-butyl-p-benzoquinone; palladium(II) trifluoroacetate; racemic methyl phenyl sulfoxide; zinc(II) trifluoroacetate; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane; 1,4-dioxane / 24 h / 20 °C / Inert atmosphere; Sealed tube 3: lithium hydroxide monohydrate / tetrahydrofuran / 4 h / 50 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / toluene / 4 h / Inert atmosphere 2.1: tetrahydrofuran / 0.75 h / -50 °C / Alkaline conditions; Enzymatic reaction 2.2: 7 h 3.1: tetrahydrofuran / 2 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: triethylamine / toluene / 4 h / 50 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran / 0.75 h / -50 °C / Inert atmosphere 2.2: 7 h / -78 °C / Inert atmosphere 3.1: dihydrogen peroxide / tetrahydrofuran / 2 h / 0 - 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / dichloromethane; tetrahydrofuran / 0.5 h / 0 °C 1.2: 3 h 2.1: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere 2.2: -78 - 20 °C 3.1: hydrogenchloride / ethanol; water / 6 h / Reflux 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C 4.2: 1 h / Reflux View Scheme |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 2,5-di-tert-butyl-p-benzoquinone; palladium(II) trifluoroacetate; racemic methyl phenyl sulfoxide; zinc(II) trifluoroacetate; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane; 1,4-dioxane / 24 h / 20 °C / Inert atmosphere; Sealed tube 2: lithium hydroxide monohydrate / tetrahydrofuran / 4 h / 50 °C View Scheme |
1-(methoxymethyl)piperidin-2-one
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: hydrogenchloride / ethanol; water / 6 h / Reflux 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 20 °C 3.2: 1 h / Reflux View Scheme |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: toluene / 3 h / 80 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C View Scheme |
5,6-dihydro-2(1H)-pyridinone
cis-3,4-dihydroxy-2-piperidinone
Conditions | Yield |
---|---|
osmium(VIII) oxide; 4-methylmorpholine N-oxide In tert-butyl alcohol Ambient temperature; | 100% |
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In tert-butyl alcohol for 27h; Ambient temperature; | 64 mg |
[2-(hydroxymethyl)phenyl]dimethyl(4-fluorophenyl)silane
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
With potassium hydroxide; (1R,4R)-2,5-diphenylbicyclo[2.2.2]octa-2,5-diene; bis(ethylene)rhodium(I) chloride dimer In tetrahydrofuran at 50℃; for 12h; | 92% |
Conditions | Yield |
---|---|
With (R)-2,2'-bis(diarylphosphino)-1,1'-binaphthyl; water; bis(ethylene)rhodium acetylacetonate In 1,4-dioxane at 60℃; for 12h; | 88% |
Conditions | Yield |
---|---|
With (R)-2,2'-bis(diphenylphosphino)-octahydro-1,1'-binaphthyl; water; bis(ethylene)rhodium acetylacetonate In 1,4-dioxane at 40℃; for 12h; | 84% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With sodium hydride In tetrahydrofuran; mineral oil at -5 - 0℃; for 2h; Stage #2: C13H11ClN2O In tetrahydrofuran; mineral oil for 21h; | 82% |
With triethylamine In tetrahydrofuran at 0℃; for 3h; |
Conditions | Yield |
---|---|
With titanium tetrachloride; triethylamine In dichloromethane at 0℃; for 1h; | 76% |
Conditions | Yield |
---|---|
In toluene at 20 - 80℃; for 12h; Inert atmosphere; Molecular sieve; | 75% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 10h; | 75% |
5,6-dihydro-2(1H)-pyridinone
1-chloro-5,6-dihydropyridin-2(1H)-one
Conditions | Yield |
---|---|
With N-chloro-succinimide; potassium tert-butylate In tetrahydrofuran at 20℃; for 0.666667h; Inert atmosphere; | 74% |
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.25h; Stage #2: p-phenylenediacrylic diacid dichloride In tetrahydrofuran; hexane at -78℃; for 3h; | 72% |
5,6-dihydro-2(1H)-pyridinone
2-Nitrobenzenesulfonyl chloride
1-nosyl-5,6-dihydropyridin-2(1H)-one
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-Nitrobenzenesulfonyl chloride In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; | 71% |
Conditions | Yield |
---|---|
titanium tetrachloride In 1,3,5-trimethyl-benzene for 74h; Heating; | 68.9% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: C19H31NO5 In tetrahydrofuran at -78 - 20℃; for 1h; | 67.8% |
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: C19H31NO5 In tetrahydrofuran at 20℃; for 1h; | 67.8% |
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: chloroacetyl chloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 65% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 10h; | 65% |
5,6-dihydro-2(1H)-pyridinone
cinnamyl chloride
1-cinnamoyl-5,6-dihydropyridin-2(1H)-one
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With sodium hydride In tetrahydrofuran at 0℃; for 0.25h; Inert atmosphere; Stage #2: cinnamyl chloride In tetrahydrofuran at 20℃; for 0.5h; Inert atmosphere; | 64% |
Conditions | Yield |
---|---|
In benzene at 20℃; for 504000h; Cycloaddition; | 62% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Stage #1: C10H11ClN2O With pivaloyl chloride; triethylamine In tetrahydrofuran at -20℃; for 0.75h; Stage #2: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran at -70℃; for 1.75h; | 53% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Stage #1: (2E)-3-(3,5,6-trimethylpyrazin-2-yl)prop-2-enoic acid With pivaloyl chloride; triethylamine In tetrahydrofuran; dichloromethane at -20℃; Stage #2: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran for 1h; | 53% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (E)-(E)-3-(5-methoxypyrimidin-2-yl)acrylic pivalic anhydride In tetrahydrofuran; hexane at -78℃; for 1h; | 52.23% |
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (E)-(E)-3-(5-methoxypyrimidin-2-yl)acrylic pivalic anhydride In tetrahydrofuran; hexane at -78℃; for 1h; | 52.23% |
Conditions | Yield |
---|---|
With triethylamine In benzene at 20℃; for 48h; Cycloaddition; dehydrochlorination; | 51% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: C19H31NO5 In tetrahydrofuran at -78 - 20℃; for 1h; | 49.6% |
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: C19H31NO5 In tetrahydrofuran at 20℃; for 1h; | 49.6% |
5,6-dihydro-2(1H)-pyridinone
Conditions | Yield |
---|---|
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: (E)-(E)-3-(3,5-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)acrylic pivalic anhydride In tetrahydrofuran; hexane at -78℃; for 1.5h; | 48.92% |
Stage #1: 5,6-dihydro-2(1H)-pyridinone With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: (E)-(E)-3-(3,5-dimethyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)acrylic pivalic anhydride In tetrahydrofuran at -78℃; for 1.5h; | 48.92% |
The 2(1H)-Pyridinone,5,6-dihydro-, also known as 5,6-Dihydro-2(1H)-pyridone, is an organic compound with the formula C5H7NO. With the CAS registry number 6052-73-9, its systematic name is 5,6-dihydropyridin-2(1H)-one.
Physical properties of 2(1H)-Pyridinone,5,6-dihydro-: (1)ACD/LogP: -0.65; (2)ACD/LogD (pH 5.5): -0.65; (3)ACD/LogD (pH 7.4): -0.65; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 10.57; (7)ACD/KOC (pH 7.4): 10.57; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Index of Refraction: 1.478; (11)Molar Refractivity: 26.14 cm3; (12)Molar Volume: 92.2 cm3; (13)Surface Tension: 33.2 dyne/cm; (14)Density: 1.052 g/cm3; (15)Flash Point: 158 °C; (16)Enthalpy of Vaporization: 52.61 kJ/mol; (17)Boiling Point: 287 °C at 760 mmHg; (18)Vapour Pressure: 0.00256 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C1\C=C/CCN1
(2)InChI: InChI=1/C5H7NO/c7-5-3-1-2-4-6-5/h1,3H,2,4H2,(H,6,7)
(3)InChIKey: OXRRHYRRQWIHIV-UHFFFAOYAD
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