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CAS No.: | 14631-20-0 |
---|---|
Name: | N4-Acetylcytosine |
Article Data: | 29 |
Molecular Structure: | |
Formula: | C6H7N3O2 |
Molecular Weight: | 153.14 |
Synonyms: | Acetamide,N-(1,2-dihydro-2-oxo-4-pyrimidinyl)- (8CI,9CI);Cytosine, N-acetyl- (6CI);2(1H)-Pyrimidinone, 4-(acetylamino)-;4-N-Acetylcytosine;N-Acetylcytosine;Acetamide,N-(2,3-dihydro-2-oxo-4-pyrimidinyl)-;NSC 210403; |
EINECS: | 619-683-7 |
Density: | 1.41 g/cm3 |
Melting Point: | >300 °C(lit.) |
Hazard Symbols: | Xi |
Risk Codes: | 36/37/38 |
Safety: | 22-24/25-37/39-26 |
PSA: | 75.11000 |
LogP: | 0.21360 |
Conditions | Yield |
---|---|
With phosphoric acid at 100℃; for 8h; | 98% |
With pyridine for 2.5h; Heating; | 97.2% |
With pyridine at 20℃; for 24h; | 85% |
4-Amino-1-(2,5-anhydro-β-D-arabinofuranosyl)pyrimidin-2(1H)-one
A
4-N-Acetylcytosine
B
4-Acetamido-1-(2,3-di-O-acetyl-5-bromo-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2(1H)-one
C
4-Amino-1-(5-bromo-5-deoxy-β-D-arabinofuranosyl)pyrimidin-2(1H)-one
Conditions | Yield |
---|---|
With hydrogen bromide In N,N-dimethyl-formamide at 120℃; for 0.416667h; | A 20% B 3% C 45% |
N-acetylcytidine
A
4-N-Acetylcytosine
B
N4,O5'-diacetyl-2',3'-dideoxycytidine
C
N4-acetyl-5'-O-(acetoxyisobutyryl)-2',3'-dideoxycytidine
Conditions | Yield |
---|---|
Yield given. Multistep reaction. Yields of byproduct given; |
N4-acetyl-O5'-trityl-2'deoxy-cytidine
A
4-N-Acetylcytosine
B
4,5-dihydro-5-trityloxymethylfuran-4-one
Conditions | Yield |
---|---|
With pyridine; chromium(VI) oxide; acetic anhydride In dichloromethane Ambient temperature; 45 - 60 min; |
4-N-Acetylcytosine
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane at 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
100% |
4-N-Acetylcytosine
N-(1,2,2,2-tetrachloroethyl)benzamide
N-[1-(4-Acetylamino-2-oxo-2H-pyrimidin-1-yl)-2,2,2-trichloro-ethyl]-benzamide
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetone at 0℃; for 0.5h; | 99% |
4-N-Acetylcytosine
1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose
(2R,3R,4S)-2-(4-acetamido-2-oxopyrimidin-1(2H)-yl)-4-(benzyloxy)-5,5-bis(((methylsulfonyl)oxy)methyl)tetrahydrofuran-3-yl acetate
Conditions | Yield |
---|---|
Stage #1: 4-N-Acetylcytosine; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Reflux; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 5.5h; Reflux; Inert atmosphere; | 96% |
Stage #1: 4-N-Acetylcytosine; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile for 1h; Heating; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile for 3h; Heating; Further stages.; | 82% |
With N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate In acetonitrile | 82% |
Stage #1: 4-N-Acetylcytosine; 1,2-di-O-acetyl-5-O-methanesulfonyl-4-C-methanesulfonyloxymethyl-3-O-benzyl-D-erythro-pentofuranose With N,O-bis-(trimethylsilyl)-acetamide In acetonitrile at 40℃; for 0.333333h; Stage #2: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at 20℃; for 2.5h; Heating / reflux; | 60% |
4-N-Acetylcytosine
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate
(1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5S)-5-[4-(methylcarboxamido)-2-oxo-1,2-dihydro-1-pyrimidinyl]-1,3-oxathiolane-2-carboxylate
Conditions | Yield |
---|---|
Stage #1: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl (2R,5R)-5-(methylcarbonyloxy)-1,3-oxathiolane-2-carboxylate With triethylsilane; iodine In dichloromethane at 0℃; for 1h; Inert atmosphere; Stage #2: 4-N-Acetylcytosine With N,O-bis-(trimethylsilyl)-acetamide In dichloromethane at 0 - 20℃; for 1h; Reagent/catalyst; Inert atmosphere; stereoselective reaction; | 95% |
Molecule structure of N4-Acetylcytosine (CAS NO.14631-20-0):
IUPAC Name: N-(2-Oxo-1H-pyrimidin-6-yl)acetamide
Molecular Weight: 153.13868 g/mol
Molecular Formula: C6H7N3O2
Density: 1.41 g/cm3
Melting Point: >300 °C(lit.)
Index of Refraction: 1.625
Molar Refractivity: 38.32 cm3
Molar Volume: 108.3 cm3
Surface Tension: 54.4 dyne/cm
XLogP3: -2.4
H-Bond Donor: 2
H-Bond Acceptor: 2
Rotatable Bond Count: 1
Tautomer Count: 9
Exact Mass: 153.053826
MonoIsotopic Mass: 153.053826
Topological Polar Surface Area: 70.6
Heavy Atom Count: 11
Canonical SMILES: CC(=O)NC1=CC=NC(=O)N1
InChI: InChI=1S/C6H7N3O2/c1-4(10)8-5-2-3-7-6(11)9-5/h2-3H,1H3,(H2,7,8,9,10,11)
InChIKey: IJCKBIINTQEGLY-UHFFFAOYSA-N
Product Categories of N4-Acetylcytosine (CAS NO.14631-20-0): Heterocyclic Compounds; Biochemistry; Nucleobases and their analogs; Nucleosides, Nucleotides & Related Reagents; Building Blocks; Heterocyclic Building Blocks; Pyrimidines
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-37/39-26
S22:Do not breathe dust.
S24/25:Avoid contact with skin and eyes.
S37/39:Wear suitable gloves and eye/face protection.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
N4-Acetylcytosine (CAS NO.14631-20-0) is also named as Acetamide, N-(1,2-dihydro-2-oxo-4-pyrimidinyl)- ; N-(2-Oxo-1,2-dihydro-4-pyrimidinyl)acetamide ; N-(2-Oxo-1,2-dihydropyrimidin-4-yl)acetamid ; N-Acetylcytosine .