[1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid
gabapentin-lactam
Conditions | Yield |
---|---|
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 40℃; for 3.5h; Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=8.2 - 8.8; Product distribution / selectivity; Heating / reflux; | 100% |
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide; sodium hypochlorite In water at 0 - 50℃; for 3h; Stage #2: With hydrogenchloride In water at 100 - 105℃; for 3h; pH=11 - 12; Product distribution / selectivity; | 93.8% |
Stage #1: [1-(2-amino-2-oxoethyl)cyclohexyl]acetic acid With sodium hydroxide In water at 20 - 30℃; for 0.5h; Stage #2: With sode de l'acide trichloroisocyanurique In water at 0 - 20℃; for 5h; Stage #3: In water; toluene at 80℃; for 8h; Reagent/catalyst; | 85% |
Multi-step reaction with 2 steps 1.1: trichloroisocyanuric acid / methanol / 1.75 h / 20 - 25 °C 2.1: sodium hydroxide / water / 4 h / 0 - 20 °C 2.2: 8 h / 80 °C View Scheme |
(1-cyanocyclohexyl)-acetic acid
gabapentin-lactam
Conditions | Yield |
---|---|
Stage #1: (1-cyanocyclohexyl)-acetic acid With sodium hydroxide In water pH=12; Stage #2: With hydrogen In water; toluene at 80 - 85℃; under 3750.38 - 7500.75 Torr; Inert atmosphere; | 97.3% |
With chromium-promoted Raney-nickel; hydrogen In water at 110℃; under 15757.7 Torr; for 9h; Reagent/catalyst; Temperature; Autoclave; | 95.3% |
(1-cyanocyclohexyl)acetonitrile
gabapentin-lactam
Conditions | Yield |
---|---|
Stage #1: (1-cyanocyclohexyl)acetonitrile With sodium hydrogencarbonate at 25℃; for 28h; pH=7.4 - 7.5; Enzymatic reaction; Stage #2: With sodium hydroxide In water at 20℃; Stage #3: With hydrogen In water at 80℃; under 7500.75 Torr; Concentration; Time; Inert atmosphere; | 93.63% |
3-azaspiro[5,5]undecane-2,4-dione
gabapentin-lactam
Conditions | Yield |
---|---|
With methanol; tert-butylhypochlorite; potassium tert-butylate; potassium bromide at 60℃; for 24h; Hofmann type rearrangement; Inert atmosphere; | 92% |
With bromine; sodium hydroxide In water at 0 - 85℃; Product distribution / selectivity; |
1-(aminomethyl)cyclohexaneacetic acid potassium salt
gabapentin-lactam
Conditions | Yield |
---|---|
With 4-methyl-morpholine; bis(trichloromethyl) carbonate; potassium hydroxide In water; acetonitrile at 20℃; for 0.00277778h; Inert atmosphere; | 92% |
gabapentin-lactam
Conditions | Yield |
---|---|
With Raney Nickel In water at 80℃; under 7500.75 Torr; for 18h; pH=13.5; | 91.9% |
ethyl 1-nitromethyl-1-cyclohexaneacetate
gabapentin-lactam
Conditions | Yield |
---|---|
In palladium-carbon; ethanol | 91.6% |
gabapentin-lactam
Conditions | Yield |
---|---|
With nickel In ethanol at 110℃; for 21h; | 90% |
gabapentin-lactam
Conditions | Yield |
---|---|
With hydrogen In water at 80℃; under 7500.75 Torr; for 20h; pH=13.5; | 90% |
gabapentin-lactam
Conditions | Yield |
---|---|
Stage #1: C10H16ClNO3 With sodium hydroxide In water at 0 - 20℃; for 4h; Stage #2: In toluene at 80℃; for 8h; | 90% |
2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one
gabapentin-lactam
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate In water; acetonitrile at 20℃; | 83% |
gabapentin-lactam
Conditions | Yield |
---|---|
With ammonia Zersetzen des Ammoniumsalzes mit 1.1 Mol 10%iger Natronlauge, Behandeln des Reaktionsprodukts mit alkal.Kaliumhypobromit-Loesung, zuletzt bei 70-75grad, und Eindampfen mit Salzsaeure; |
gabapentin-lactam
Conditions | Yield |
---|---|
With magnesium monoperoxyphthalate hexahydrate In methanol at 20℃; for 3h; | 39 mg |
1-cyclohexene-1-carboxaldehyde
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: CH2Cl2 / 20 °C 2.1: DMAB; methanesulfonic acid / diethyl ether / 3 h / 0 °C 2.2: 81 percent / pyridine / CH2Cl2 / 0 °C 3.1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C 4.1: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C View Scheme |
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: DMAB; methanesulfonic acid / diethyl ether / 3 h / 0 °C 1.2: 81 percent / pyridine / CH2Cl2 / 0 °C 2.1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C 3.1: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C View Scheme |
N'-(1-cyclohexenylmethyl)-N'-trichloroacetylbenzohydrazide
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 77 percent / CuCl; TMEDA / acetonitrile / 20 h / 60 °C 2: 90 percent / Raney-Ni / ethanol / 21 h / 110 °C View Scheme |
[1-Cyclohexyl-meth-(E)-ylidene]-(4-methoxy-benzyl)-amine
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: toluene / 1 h / 0 - 20 °C 1.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C 2.1: 26 percent / tributyltin hydride 3.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 4.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: toluene / 1 h / 0 - 20 °C 1.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C 2.1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating 3.1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating 4.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 5.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme |
cyclohexanecarbaldehyde
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: toluene / Heating 2.1: toluene / 1 h / 0 - 20 °C 2.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C 3.1: 26 percent / tributyltin hydride 4.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 5.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme | |
Multi-step reaction with 6 steps 1.1: toluene / Heating 2.1: toluene / 1 h / 0 - 20 °C 2.2: 798 mg / triethylamine / toluene / 2 h / 0 - 20 °C 3.1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating 4.1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating 5.1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 6.1: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme |
4,4,6-trichloro-2-(dimethylamino)-2-azaspiro[4.5]decan-3-one
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Raney nickel; water / ethanol / 110 °C 2: 39 mg / magnesium monoperoxyphthalate hexahydrate / methanol / 3 h / 20 °C View Scheme |
1-hydroxy-2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 2: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme |
2,2,2-trichloro-N-(cyclohexylidenemethyl)-N-(4-methoxybenzyl)acetamide
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 26 percent / tributyltin hydride 2: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 3: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1: 2,2'-bipyridine; copper(I) chloride / toluene / 11 h / Heating 2: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating 3: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 4: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme |
1,4,4-trichloro-2-(4-methoxybenzyl)-2-azaspiro[4.5]decan-3-one
gabapentin-lactam
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 68 mg / AIBN; tributyltin hydride; water / toluene / 0.75 h / Heating 2: 55 percent / triethylsilane; trifluoroacetic acid / CH2Cl2 / 0.5 h / 20 °C 3: 83 percent / cerium(IV) ammonium nitrate / acetonitrile; H2O / 20 °C View Scheme |
C
gabapentin-lactam
E
H-Gpn-OH
Conditions | Yield |
---|---|
With sodium hydroxide; pyrographite In water at 5 - 75℃; for 8h; Conversion of starting material; |
B
gabapentin-lactam
D
H-Gpn-OH
Conditions | Yield |
---|---|
With sodium hydroxide; pyrographite In water at 0 - 70℃; for 6h; Conversion of starting material; | |
With sodium hydroxide; pyrographite In water at 10 - 80℃; for 11.5h; Conversion of starting material; | |
With sodium hydroxide; pyrographite In water at 5 - 75℃; for 11.5h; Conversion of starting material; |
Conditions | Yield |
---|---|
With sodium hydroxide; pyrographite In water at 80 - 85℃; for 2h; |
ethyl 2-(1-formylcyclohexyl)acetate
gabapentin-lactam
Conditions | Yield |
---|---|
Stage #1: ethyl 2-(1-formylcyclohexyl)acetate With ammonia In ethanol at 20℃; for 48h; Stage #2: With hydrogen; acetic acid; 5%-palladium/activated carbon at 80 - 100℃; under 2844.39 Torr; for 3h; Product distribution / selectivity; |
gabapentin-lactam
di-tert-butyl dicarbonate
3-oxo-2-aza-spiro[4.5]decane-2-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With dmap In acetonitrile at 25℃; | 92% |
3-phenyl-propionaldehyde
gabapentin-lactam
Conditions | Yield |
---|---|
With acetic acid In toluene at 110℃; for 12h; Dean-Stark; | 92% |
gabapentin-lactam
Conditions | Yield |
---|---|
With hydrogenchloride In water at 80 - 90℃; for 5h; Heating / reflux; | 90.9% |
With hydrogenchloride; water for 24h; Reflux; | 90% |
With hydrogenchloride; water at 100℃; for 10h; | 90% |
gabapentin-lactam
diisopropyl hydrogenphosphonate
diisopropyl(3-oxo-2-azaspiro[4,5]decan-2-yl)phosphonate
Conditions | Yield |
---|---|
With copper diacetate; potassium carbonate In toluene at 80℃; under 760.051 Torr; for 0.666667h; Reagent/catalyst; Molecular sieve; | 87% |
Conditions | Yield |
---|---|
Stage #1: gabapentin-lactam With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; 9-azanoradamantane N-oxyl; oxygen; copper(l) chloride In tetrahydrofuran at 23℃; for 1h; Molecular sieve; | 87% |
gabapentin-lactam
para-thiocresol
Conditions | Yield |
---|---|
With potassium fluoride; oxygen In 1,3,5-trimethyl-benzene at 100℃; under 760.051 Torr; for 1h; Autoclave; | 76% |
gabapentin-lactam
toluene-4-sulfonamide
Conditions | Yield |
---|---|
With diazoacetic acid ethyl ester; manganese(II) perchlorate hexahydrate In cyclohexane at 90℃; for 12h; chemoselective reaction; | 72% |
gabapentin-lactam
Boc-Glu(OBzl)-OH
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 5h; | 60% |
gabapentin-lactam
1-aminomethyl-1-cyclohexaneacetic acid hydrobromide
Conditions | Yield |
---|---|
With water; hydrogen bromide at 0 - 114℃; for 6 - 24h; Product distribution / selectivity; Heating / reflux; | 59.27% |
With water; hydrogen bromide at 0 - 114℃; for 24 - 45h; Product distribution / selectivity; Heating / reflux; | 59.27% |
BOC-glycine
gabapentin-lactam
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 20℃; for 5h; | 57% |
Conditions | Yield |
---|---|
With copper(l) iodide; potassium carbonate; 1,3-bis(methylamino)propane In 1,4-dioxane for 24h; Reflux; | 50% |
The Gabapentin-lactam, with the CAS registry number 64744-50-9, is also known as beta,beta-Pentamethylen-gamma-butyrolactam. It belongs to the product categories of Intermediates of Gabapentin; (Intermediate of gabapentin); Heterocyclic Compounds; Intermediates & Fine Chemicals; Neurochemicals; Pharmaceuticals. This chemical's molecular formula is C9H15NO and molecular weight is 153.2215. Its IUPAC name is called 3-azaspiro[4.5]decan-2-one. This chemical's classification code is Drug / Therapeutic Agent. This chemical is white solid which reduces protein aggregates and improves motor performance in a transgenic mouse model of Huntington disease. What's more, this chemical opens mitochondrial ATP-dependent potassium channels. When you are using this chemical, please be cautious about it. You should not breathe its dust. In addition, you must avoid contacting it with skin and eyes.
Physical properties of Gabapentin-lactam: (1)ACD/LogP: 0.62; (2)ACD/LogD (pH 5.5): 0.62; (3)ACD/LogD (pH 7.4): 0.62; (4)ACD/BCF (pH 5.5): 1.76; (5)ACD/BCF (pH 7.4): 1.76; (6)ACD/KOC (pH 5.5): 52.07; (7)ACD/KOC (pH 7.4): 52.07; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Index of Refraction: 1.509; (11)Molar Refractivity: 43.4 cm3; (12)Molar Volume: 145.2 cm3; (13)Surface Tension: 38.1 dyne/cm; (14)Density: 1.05 g/cm3; (15)Flash Point: 192.3 °C; (16)Enthalpy of Vaporization: 57.27 kJ/mol; (17)Boiling Point: 330.1 °C at 760 mmHg; (18)Vapour Pressure: 0.000169 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1CCC2(CC1)CC(=O)NC2
(2)InChI: InChI=1S/C9H15NO/c11-8-6-9(7-10-8)4-2-1-3-5-9/h1-7H2,(H,10,11)
(3)InChIKey: JAWPQJDOQPSNIQ-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rat | LD50 | intravenous | 125mg/kg (125mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Arzneimittel-Forschung. Drug Research. Vol. 10, Pg. 243, 1960. |
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