Application of 2-(1-adamantane formamido) ethyl formate compound as bactericide
A technology of adamantanecarboxamido and ester compounds, which is applied in the application field of 2-(1-adamantanecarboxamido) ethyl formate as a fungicide, can solve the structure and biological activity research. Literature reports, etc.
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Embodiment 1
[0026] Synthesis of Example 1 Compound Ia (R=phenyl):
[0027] Dissolve 1.5 mmol of benzoyl chloride in 5 mL of tetrahydrofuran to prepare a tetrahydrofuran solution (5 mL) of benzoyl chloride (1.5 mmol).
[0028] The intermediate N-2-hydroxyethyl-1-adamantanecarboxamide (0.335g, 1.5mmol), tetrahydrofuran (10mL) and acid-binding agent triethylamine (1.8mmol) were mixed, stirred and dissolved, and placed in an ice bath A solution of benzoyl chloride (1.5 mmol) in tetrahydrofuran (5 mL) was slowly added dropwise. After the dropwise addition, react at room temperature for 3h, then filter to remove the hydrochloride of triethylamine generated by the reaction, and the filtrate is rotary evaporated to remove solvent tetrahydrofuran, and the obtained rotary evaporation residue is separated by column chromatography (eluent is a volume ratio of 1: 5 (mixture of ethyl acetate and petroleum ether) to obtain a white solid, which is benzoic acid-2-(1-adamantanecarboxamido)ethyl, and the c...
Embodiment 2
[0031] The synthesis of embodiment 2 compound Ib (R=2-chlorophenyl):
[0032] The intermediate N-2-hydroxyethyl-1-adamantanecarboxamide (0.335g, 1.5mmol), tetrahydrofuran (12mL) and acid-binding agent triethylamine (2.7mmol) were mixed, stirred and dissolved, and placed in an ice bath A solution of 2-chlorobenzoyl chloride (2.0 mmol) in tetrahydrofuran (6 mL) was slowly added dropwise. After the dropwise addition, react at room temperature for 4 h, filter and remove the hydrochloride filtrate of triethylamine by rotary evaporation to remove solvent tetrahydrofuran, and the obtained rotary evaporation residue is separated by column chromatography (eluent is ethyl acetate with a volume ratio of 1:4 mixed solution with petroleum ether) to obtain a white solid, which is 2-(1-adamantanecarboxamido)ethyl 2-chlorobenzoate, and the calculated yield is 65.3%. m.p.:120~123℃;
[0033] 1 H NMR (500MHz, CDCl 3 )δ7.83(dd,J=7.5,1.0Hz,1H),7.49–7.42(m,2H),7.37–7.32(m,1H),6.11(s,1H),4.44(t,...
Embodiment 3
[0035] Synthesis of Example 3 Compound Ic (R=3-chlorophenyl):
[0036] The intermediate N-2-hydroxyethyl-1-adamantanecarboxamide (0.335g, 1.5mmol), tetrahydrofuran (12mL) and acid-binding agent triethylamine (2.7mmol) were mixed, stirred and dissolved, and placed in an ice bath A solution of 3-chlorobenzoyl chloride (2.0 mmol) in tetrahydrofuran (6 mL) was slowly added dropwise. After the dropwise addition, react at room temperature for 3h, then filter to remove the hydrochloride of triethylamine generated by the reaction, and the filtrate is rotary evaporated to remove solvent tetrahydrofuran, and the obtained rotary evaporation residue is separated by column chromatography (eluent is a volume ratio of 1: 3 mixed solution of ethyl acetate and petroleum ether) to obtain a white solid, which is 2-(1-adamantanecarboxamido)ethyl 3-chlorobenzoate, and the calculated yield is 52.5%. m.p.:127~130℃;
[0037] 1 H NMR (500MHz, CDCl 3 )δ7.94(s,1H),7.86(d,J=7.5Hz,1H),7.48(d,J=7.5Hz,1...
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