A 9s-acyloxy cinchonine derivative and its preparation method and application, botanical insecticide
A technology of acyloxy cinchonines and derivatives, which is applied in the field of botanical pesticides and can solve problems such as unreported research
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Embodiment 14
[0049] This embodiment is the preparation method of compound 3a in embodiment 1, specifically comprising the following steps:
[0050] (1) Weigh 0.5mmol of cinchonine (1), 0.6mmol of glacial acetic acid (2a), 0.6mmol of DCC and 0.1mmol of DMAP in a 50mL flask and mix well, then add 10mL of calcium hydride dried Dichloromethane, react at room temperature after mixing evenly, adopt TLC tracking detection in the reaction process, the reaction ends after the raw material reaction is complete;
[0051](2) Then remove urea by filtration to obtain the filtrate; the filtrate is diluted with 40 mL of dichloromethane, and then the diluted solution is sequentially washed with 0.1mol / L hydrochloric acid (25 mL), saturated sodium bicarbonate solution (25 mL) and saturated Brine (25mL) was washed successively, and then dried with anhydrous sodium sulfate; the dried dilution was distilled off under reduced pressure to remove the solvent to obtain a solid, and then the solid was separated by ...
Embodiment 15
[0057] This example is the preparation method of compound 3b, specifically refer to the preparation process of Example 14, the only difference is: replace glacial acetic acid (2a) with n-hexanoic acid (2b), the reaction involved is:
[0058]
[0059] The yield of compound 3b prepared by the preparation method of this example was 39%. Carry out 400MHz proton nuclear magnetic resonance spectrum test to the obtained compound 3b, the solvent that adopts during the test is CDCl 3 , TMS is the internal standard, and the test results are as follows figure 2 Shown, the specific chemical shift δ of each peak is: 8.88 (d, J=4.4Hz, 1H), 8.22 (dd, J=8.8Hz, 1.2Hz, 1H), 8.13 (dd, J=8.4Hz, 1.2Hz , 1H), 7.69-7.73(m, 1H), 7.57-7.61(m, 1H), 7.38(d, J=4.4Hz, 1H), 6.56(d, J=7.2Hz, 1H), 5.98-6.07( m, 1H), 5.07-5.13(m, 2H), 3.33(q, J=8.4Hz, 1H), 2.85-2.95(m, 2H), 2.65-2.80(m, 2H), 2.32-2.41(m, 2H), 2.22-2.29(m, 1H), 1.80-1.85(m, 2H), 1.51-1.58(m, 3H), 1.19-1.29(m, 4H), 0.89-0.98(m, 2H), 0.86...
Embodiment 16
[0062] This example is the preparation method of compound 3c, specifically refer to the preparation process of Example 14, the only difference is: replace glacial acetic acid (2a) with benzoic acid (2c), the reaction involved is:
[0063]
[0064] The yield of compound 3c prepared by the preparation method of this example was 54%. Carry out 400MHz proton nuclear magnetic resonance spectrum test to the obtained compound 3c, the solvent that adopts during the test is CDCl 3 , TMS is the internal standard, and the test results are as follows image 3 Shown, the specific chemical shift δ of each peak is: 8.87 (d, J=4.4Hz, 1H), 8.32 (dd, J=8.4Hz, 1.2Hz, 1H), 8.08-8.14 (m, 3H), 7.70- 7.74(m, 1H), 7.57-7.65(m, 2H), 7.44-7.48(m, 3H), 6.80(d, J=7.2Hz, 1H), 5.98-6.07(m, 1H), 5.06-5.13( m, 2H), 3.48(q, J=8.4Hz, 1H), 2.90-3.03(m, 2H), 2.68-2.85(m, 2H), 2.25-2.32(m, 1H), 1.94-2.01(m, 1H), 1.85-1.87 (m, 1H), 1.56-1.69 (m, 3H).
[0065] The high resolution chromatography (HRMS, ESI) t...
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