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CAS No.: | 29342-05-0 |
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Name: | Ciclopirox |
Article Data: | 12 |
Molecular Structure: | |
Formula: | C12H17NO2 |
Molecular Weight: | 207.272 |
Synonyms: | 2(1H)-Pyridone,6-cyclohexyl-1-hydroxy-4-methyl- (8CI);2(1H)-Pyridinone,6-cyclohexyl-1-hydroxy-4-methyl-;HOE 296b;Penlac; |
EINECS: | 249-577-2 |
Density: | 1.193 g/cm3 |
Melting Point: | 144 °C |
Boiling Point: | 350 °C at 760 mmHg |
Flash Point: | 165.5 °C |
Solubility: | soluble in methanol, ethanol or chloroform |
Appearance: | white or light-yellow powder |
Hazard Symbols: | C,O |
Risk Codes: | R8; R35; R34; R20 |
PSA: | 42.23000 |
LogP: | 2.44170 |
CICLOPIROX
Conditions | Yield |
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Stage #1: 2-cyclohexyl-6-methoxy-4-methylpyridine N-oxide With acetyl chloride for 1h; Reflux; Stage #2: With methanol at 20℃; | 95% |
cyclopirox olamine
CICLOPIROX
Conditions | Yield |
---|---|
With hydrogenchloride In water | 84% |
With hydrogenchloride In water; ethyl acetate | 84% |
Conditions | Yield |
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Stage #1: Methyl 3,3-dimethylacrylate; cyclohexanylcarbonyl chloride With aluminum (III) chloride In dichloromethane for 3h; Reflux; Stage #2: With hydroxylamine hydrochloride; sodium acetate In methanol; water at 20 - 30℃; for 20h; Stage #3: With sodium hydroxide In methanol; water at 20℃; for 1h; | 34% |
With hydroxylamine hydrochloride; sodium acetate 2.) water, methanol, 25 deg C, 20 h; Yield given. Multistep reaction; |
4-methyl-6-cyclohexyl02-pyrone
CICLOPIROX
Conditions | Yield |
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With 1H-imidazole; hydroxyammonium sulfate at 90℃; for 5h; | 11.8 g |
Conditions | Yield |
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With hydroxylamine sulfate | |
With hydroxylamine sulfate |
Conditions | Yield |
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With hydroxylamine hydrochloride In dichloromethane |
2-aminopyridine
2-Amino-6-methylpyridine
4-methyl-6-cyclohexyl02-pyrone
CICLOPIROX
Conditions | Yield |
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With hydroxylamine |
CICLOPIROX
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 1-acetoxy-1,2-benziodoxol-3-one; trifluoroacetic acid / water; dichloromethane / 24 h / 20 °C / Schlenk technique; Inert atmosphere; Irradiation 2.1: acetyl chloride / 1 h / Reflux 2.2: 20 °C View Scheme |
2-methoxy-4-methyl pyridine
CICLOPIROX
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 12 h / 0 - 20 °C 2.1: tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 1-acetoxy-1,2-benziodoxol-3-one; trifluoroacetic acid / water; dichloromethane / 24 h / 20 °C / Schlenk technique; Inert atmosphere; Irradiation 3.1: acetyl chloride / 1 h / Reflux 3.2: 20 °C View Scheme |
3-Methylbutenoic acid
CICLOPIROX
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: sulfuric acid / 5 h / Reflux 2.1: aluminum (III) chloride / dichloromethane / 3 h / Reflux 2.2: 20 h / 20 - 30 °C 2.3: 1 h / 20 °C View Scheme |
1. Introduction of Ciclopirox
Ciclopirox is one kind of white or light-yellow powder. It is soluble in methanol, ethanol or chloroform, slightly soluble in DMF or water, slightly soluble in ethyl ether. The IUPAC Name of it is 6-Cyclohexyl-1-hydroxy-4-methylpyridin-2-one. It belongs to Intermediates & Fine Chemicals;Pharmaceuticals;Heterocycles. In addition, the Classification Code of it is Anti-Infective Agents; Antifungal; Antifungal Agents.
2. Properties of Ciclopirox
Physical properties about Ciclopirox are:
(1)Melting Point: 144 °C; (2)Density: 1.193 g/cm3; (3)Boiling Point: 350 °C at 760 mmHg; (4)Flash Point: 165.5 °C; (5)Molar Volume: 173.6 cm3; (6)Polarizability: 22.98×10-24 cm3; (7)Surface Tension: 51.7 dyne/cm; (8)Enthalpy of Vaporization: 68.85 kJ/mol; (9)Vapour Pressure: 2.71E-06 mmHg at 25 °C; (10)log P (octanol-water): 2.730 (none); (11)XLogP3-AA: 2; (12)H-Bond Donor: 1; (13)H-Bond Acceptor: 2; (14)Rotatable Bond Count: 1; (15)Exact Mass: 207.125929; (16)MonoIsotopic Mass: 207.125929; (17)Topological Polar Surface Area: 40.5; (18)Heavy Atom Count: 15; (19)Complexity: 325.
3. Structure Descriptors of Ciclopirox
(1)Canonical SMILES: CC1=CC(=O)N(C(=C1)C2CCCCC2)O
(2)InChI: InChI=1S/C12H17NO2/c1-9-7-11(13(15)12(14)8-9)10-5-3-2-4-6-10/h7-8,10,15H,2-6H2,1H3
(3)InChIKey: SCKYRAXSEDYPSA-UHFFFAOYSA-N
(4)Smiles: c1(cc(cc(n1O)C1CCCCC1)C)=O
4. Physical Properties of Ciclopirox
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 144 | deg C | EXP | |
log P (octanol-water) | 2.730 | (none) | EST | |
Atmospheric OH Rate Constant | 7.97E-11 | cm3/molecule-sec | 25 | EST |