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| | 2-Azabicyclo[2.2.1]hept-5-en-3-one Basic information |
| | 2-Azabicyclo[2.2.1]hept-5-en-3-one Chemical Properties |
| Melting point | 54-58 °C(lit.) | | Boiling point | 102-106 °C0.25 mm Hg(lit.) | | density | 1.1143 (rough estimate) | | vapor pressure | 0.3-1.06Pa at 25-40℃ | | refractive index | 1.5040 (estimate) | | Fp | >230 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 15.48±0.20(Predicted) | | form | Crystalline Powder | | color | Off-white to beige | | Water Solubility | >1000 g/L (23 ºC) | | BRN | 508342 | | InChI | 1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1 | | InChIKey | DDUFYKNOXPZZIW-UHFFFAOYSA-N | | SMILES | O=C1N[C@H]2C[C@@H]1C=C2 | | LogP | -0.14 at 20℃ | | Surface tension | 69.9mN/m at 1g/L and 20℃ | | CAS DataBase Reference | 49805-30-3(CAS DataBase Reference) |
| Hazard Codes | Xi,Xn | | Risk Statements | 36/37/38-43-22 | | Safety Statements | 26-36-36/37 | | WGK Germany | 1 | | HS Code | 29337900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Oral
Skin Sens. 1 |
| | 2-Azabicyclo[2.2.1]hept-5-en-3-one Usage And Synthesis |
| Chemical Properties | solid | | Uses | Intermediate for pharmaceuticals. Product Data Sheet | | Uses | Abacavir intermediate. 2-Azabicyclo[2.2.1]hept-5-en-3-one is used as an intermediate in the synthesis of carbocyclic sugar amines, carbanucleosides, and carbocyclic dinucleotide analogues. | | Uses | 2-Azabicyclo[2.2.1]hept-5-en-3-one was used in:
- preparation of (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine, a precursor of analog of bredinin
- synthesis of therapeutic drugs
- chemoenzymatic synthesis of ()-carbovir
| | General Description | 2-Azabicyclo[2.2.1]hept-5-en-3-one is also referred as vince lactam. It is a versatile intermediate in the synthesis of carbocyclic nucleosides. 2-Azabicyclo[2.2.1]hept-5-en-3-one and its monohydrated complex was investigated in a supersonic jet by Fourier transform microwave spectroscopy. | | Synthesis | In a 1000 mL reaction flask equipped with a thermometer and an off-gas absorption device, 500 mL of methanol, 50 g of cross-linked polystyrene-sulfinyl and 5.0 g of cyclopentadiene were added. The reaction system was cooled to 0-5°C and 2.5 g of cyanogen chloride gas was slowly passed through, while an ethanol solution of 5% sodium hydroxide was added dropwise to maintain the pH of the reaction system between 4-5. After the dropwise addition, the reaction was continued for 8 hours. After completion of the reaction, the solid was separated by filtration. The resulting solid was added to 100 mL of 5% ethanol solution of acetic acid and the reaction was continued for 8 hours at room temperature. Subsequently, the solid catalyst particles were removed by filtration and the filtrate was concentrated to afford the white crystalline product 2-azabicyclo[2.2.1]hept-5-en-3-one in a yield of 4.21 g in 95% yield (as cyanogen chloride) and 99.5% purity. | | References | [1] Patent: CN107805217, 2018, A. Location in patent: Paragraph 0036-0043 |
| | 2-Azabicyclo[2.2.1]hept-5-en-3-one Preparation Products And Raw materials |
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