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A kind of octahydroacridine skeleton with three continuous chiral centers and preparation method thereof

A technology of octahydroacridine and skeleton, which is applied in the field of octahydroacridine skeleton and its preparation, and can solve the problems of low universality of the skeleton, low yield of octahydroacridine, complex synthesis process, etc.

Active Publication Date: 2021-05-14
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But above-mentioned two kinds of methods exist the defect that synthesis technique is complicated, yield is not high and the universality of synthetic octahydroacridine skeleton is not high

Method used

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  • A kind of octahydroacridine skeleton with three continuous chiral centers and preparation method thereof
  • A kind of octahydroacridine skeleton with three continuous chiral centers and preparation method thereof
  • A kind of octahydroacridine skeleton with three continuous chiral centers and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040]Dissolve 0.2 mmol of N-Ts anthranilaldehyde in 1 mL of a mixed solvent of pyridine and toluene (the volume ratio of pyridine to toluene is 7:3), then add 0.04 mmol of catalyst silane-modified 4-hydroxyproline, and then add 0.5 mmol cyclohexenone, then immediately placed in a constant temperature ice bath, and kept the reaction temperature at 0 ° C, after 10 hours of reaction, spot the plate, after confirming the completion of the reaction, pass the reaction solution through the chromatographic column, and use a volume ratio of 25% Ethyl acetate and petroleum ether were used for elution to obtain 69.8 mg of a white solid with a yield of 94%. The solid was tested by optical rotation, infrared, nuclear magnetic, high performance liquid chromatography and mass spectrometry.

[0041] Infrared test results such as figure 1 As shown in (a), from figure 1 (a) It can be seen that it is at 3475, 2948, 2872, 2171, 1695, 1618, 1479, 1456, 1415, 1350, 1244, 1166, 1122, 1068, 935, 86...

Embodiment 2

[0050] Dissolve 0.2mmol of 5-fluoro-N-Ts anthranilaldehyde in 1mL of a mixed solvent of pyridine and toluene (the volume ratio of pyridine to toluene is 7:3), and then add 0.04mmol of catalyst silane-modified 4-hydroxyproline , and then add 0.5mmol cyclohexenone, then immediately put it in a constant temperature ice bath, and keep the reaction temperature at 0°C, after 10 hours of reaction, spot the plate, after confirming that the reaction is complete, pass the reaction solution through the chromatographic column, and use Eluting with ethyl acetate and petroleum ether at a volume ratio of 25%, 69.8 mg of a white solid was obtained with a yield of 94%. The solid was tested by optical rotation, infrared, NMR, high performance liquid chromatography and mass spectrometry.

[0051] Infrared test results such as figure 1 As shown in (b), the product of this embodiment is at 3416,2948,2171,1693,1479,1426,1350,1248,1165,1137,942,911,880,818,679,612,544cm -1 There are characteristic ...

Embodiment 3

[0060] Dissolve 0.2mmol of 5-chloro-N-Ts anthranilaldehyde in 1mL of a mixed solvent of pyridine and toluene (the volume ratio of pyridine to toluene is 7:3), then add 0.04mmol of 4-hydroxyproline modified by catalyst silane , and then add 0.5mmol cyclohexenone, then immediately put it in a constant temperature ice bath, and keep the reaction temperature at 0°C, after 10 hours of reaction, spot the plate, after confirming that the reaction is complete, pass the reaction solution through the chromatographic column, and use Eluting with ethyl acetate and petroleum ether at a volume ratio of 15%, 77.8 mg of a white solid was obtained with a yield of 96%. The solid was tested by optical rotation, infrared, NMR, high performance liquid chromatography and mass spectrometry.

[0061] Infrared test results such as figure 1 As shown in (c), the product of this example is at 3929,3415,3237,2944, 2171,1692,1638,1618,1470,1417,1349,1305,1249,1164,1128,1088,1033,934, 820,709,670,622cm -1 ...

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Abstract

The octahydroacridine skeleton with three continuous chiral centers of the present invention has a structural formula as follows: wherein: R1 is one of H, F, Cl, Br, I and OMe; R2 is Ts, PhSO 2 , 4‑ClPhSO 2 , 4‑NO 2 PhSO 2 , 4‑CF 3 PhSO 2 and CH 3 SO 2 One of; n is 0 or 1 or 2. The octahydroacridine skeleton provided by the present invention has three continuous chiral centers and two active functional groups, and the skeleton structure is special, and the three newly generated bonds (a, b, c) on the same ring have the same direction, It is easy to derivatize into molecules with more complex structures; the present invention adopts silane-modified 4-hydroxyproline as a catalyst according to the principle of aza-diels-Alder reaction, so that the reaction is simpler and the product yield obtained is higher ; At the same time, under the action of the catalyst, the direction of the newly generated three bonds is consistent, and the structure is stable.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and asymmetric organic catalytic synthesis, in particular to an octahydroacridine skeleton with three continuous chiral centers and a preparation method thereof. Background technique [0002] A large number of nitrogen-containing heterocycles exist in natural products and drug molecular structures, among which the tetrahydroquinoline structure exhibits very important biological activities. Octahydroacridine contains tetrahydroquinoline core structure and has potential biological activity. 1,2,3,4,4a,9,9a,10-octahydroacridine is a very important inhibitor of gastric acid secretion and anti Reagents for malaria; derivatives of octahydroacridine are used in the fields of drugs, pesticides and fluorescent probes. Based on the structure of octahydroacridine, it has very important research value in medicinal chemistry, so the research and development of octahydroacridine The skeleton of the s...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D219/06C07D221/16
CPCC07D219/06C07D221/16
Inventor 阳华李双
Owner CENT SOUTH UNIV