Efficient high-stereoselectivity synthesis process of polysubstituted 3-cyclopenten-1-one
A synthesis method and technology of cyclopentenone are applied in the field of efficient and high stereoselectivity synthesis of polysubstituted 3-cyclopenten-1-one, can solve the problems of low yield, complicated reaction process and the like, and achieve high yield , The effect of easy purification of the product
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example 1
[0025] One of the I class compounds in the structural formula (R 1 =R 2 =nPr): Synthesis of trans-2,3,4,5-tetra(n-propyl)-3-cyclopenten-1-one.
[0026] Under the protection of an inert gas (such as high-purity nitrogen), add 1 mmol of 4,7-diiodo-5,6-di(n-propyl )-4,6-quinadiene and 5 mL of anhydrous and oxygen-free treated ether solvent. First, the above ether solution was lowered to a lower temperature (-78°C to -55°C) with a cold bath (such as a dry ice-acetone bath), and then 4 mmol tert-butyllithium (1.6M, n-pentane solution) was added dropwise under magnetic stirring. ). After stirring the reaction at -78°C to -55°C for 1 hour, carbon monoxide was introduced for 30 minutes. After continuing to stir the reaction at a temperature of -78°C to -30°C for 30 minutes, about 1 mL of saturated aqueous ammonium chloride solution was added to quench the reaction. Extracted three times with petroleum ether (each 10mL). The extract was washed twice with water (10 mL each time) a...
example 2
[0028] The second of class I compound in the structural formula (R 1 =SiMe 3 , R 2 =n-Hex): Synthesis of trans-2,5-bis(trimethylsilyl)-3,4-bis(n-hexyl)-3-cyclopenten-1-one.
[0029] The synthetic route is basically the same as above. The starting material diiodide compound for this synthesis is 1,4-diiodo-1,4-bis(trimethylsilyl)-2,3-bis(n-hexyl)-1,3-butadiene. 0.319 g of pure product was obtained (purity>98%, colorless liquid). Isolated yield 81%. Partial characterization data of this compound are as follows. 13 C NMR (CDCl 3 , SiMe 4 ) δ1.03, 15.65, 24.24, 29.59, 29.93, 30.93, 33.33, 54.75, 134.94, 220.79.
example 3
[0031] One of the II class compounds in the structural formula (R 1 =R 2 =nPr): Synthesis of derivative y.
[0032] The synthetic route is basically the same as above. The starting material diiodide compound of this synthesis is x. 0.154 g of pure product was obtained (purity>98%, colorless liquid). Isolated yield 70%. The NMR and high-resolution mass spectrometry data of the compound are as follows. 1 H NMR (CDCl 3 , SiMe 4 )δ0.81(t, J=7.8Hz, 6H), 1.00-1.63(m, 12H), 1.75-2.00(m, 4H), 2.63(t, J=7.0Hz, 2H). 13 C NMR (CDCl 3 , SiMe 4 )δ13.43, 18.90, 21.81, 23.15, 30.18, 53.34, 134.26, 221.10. HRMS calcd for C 15 h 24 O 220.1827, found 220.1818.
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