CAS 6746-94-7 Cyclopropylacetylene Ethynylcyclopropane
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Common Name | Cyclopropylacetylene |
CAS Number | 6746-94-7 |
Molecular Weight | 66.1 |
Molecular Formula | C5H6 |
Density | 0.7801 |
Boiling Point | 79-80 °C |
Flash Point | -5 °F |
Exact Mass | 66.046951 |
Appearance | colorless transparent liquid |
Storage condition | 2-8°C |
Cyclopropylacetylene is a key intermediate of efavirenz, a special anti-AIDS drug. Efavelan is a non-nucleoside reverse transcriptase inhibitor, which can be used in highly active antiretroviral therapy to treat human immune virus HIVTypeI.
Cyclopropylacetylene is often used as an intermediate in organic synthesis and medicinal chemistry, which can be used for the synthesis of drug molecules and bioactive molecules. For example, it is a key intermediate in the synthesis of efavirenz, a special anti-AIDS drug.
Cyclopropylacethylene, also known as ethynyl cyclopropane, is a colorless or yellow transparent liquid at normal temperature and pressure. Cyclopropanethine belongs to alkynes, and the three-membered ring in the molecular structure is not stable because of the ring tension. In addition, the boiling point of this compound is low, so it needs to be concentrated at low temperature when preparing. Cyclopropylacetylene is often used as an intermediate in organic synthesis and medicinal chemistry, and can be used for the synthesis of drug molecules and bioactive molecules. For example, it is a key intermediate in the synthesis of Efavirenz, a specific anti-AIDS drug.
Preparation method
Under the condition of stirring, methyl lithium (161.0 m L, 225.0 mmol of 1.4 M diethyl ether solution) was added dropwise to the tetrahydrofuran (300 mL) solution of α-(trichloromethyl) cyclopropyl methanol 4- methyl benzene sulfonate (50.0 mmol), and the temperature of the solution was slowly raised to zero, and the reaction was stirred at zero for more than one hour. After the reaction, the reaction was quenched with saturated ammonium chloride, the reaction solution was diluted with n-hexane, the two phases were separated, and the water phase was extracted with n-hexane (3 × 100m L). The combined organic layers were washed with brine for three times, dried with anhydrous Mg SO4, the organic extract was filtered, and the filtrate was concentrated in vacuum to obtain the target product molecules.
Organic synthesis and transformation
In the organic synthesis and transformation, the carbon-hydrogen bond on the alkynyl group in cyclopropylacetylene has a certain acidity, which can be transformed into the corresponding alkynyl anion under the action of alkali; In addition, alkynes can react with NBS under the action of silver to introduce a bromine atom at the terminal position of alkynes; The ternary ring in the structure is prone to ring-opening reaction under the action of transition metals to obtain ring-opening linear products.
Experimental steps:
N- bromosuccinimide (1.1 equivalent) and cyclopropylacetylene (1.0 equivalent) were dissolved in acetone in a round-bottomed flask, and then silver nitrate (0.10 mol%) was slowly added to the solution, and the obtained reaction mixture was stirred and reacted for 3 h at room temperature in the dark. After the reaction, the reaction mixture was concentrated under reduced pressure, and the crude product was filtered by short pad silica (pentane 100%) and separated and purified by column chromatography.
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