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Dibenzyl-macrolide compound based on photoreaction and synthesis method thereof
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A biaryl compound technology, applied in the field of chemical synthesis, can solve problems such as synthesis difficulties, and achieve the effects of simple operation, wide and easy-to-obtain raw material sources, and high atom economy
Inactive Publication Date: 2012-06-27
NANJING UNIV
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[0003] Due to the torsion of the two aryl planes in the biaryl and mesocyclic lactones, there are great difficulties in its synthesis
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Embodiment 1
[0039] Phenanthrene-9,10-dione (PQ) and 2 times the molar amount of olefin are dissolved in benzene (PQ concentration is 0.02M). Under light (400nm-760nm) conditions, the reaction was detected by TLC. After the PQ was consumed, the solvent was evaporated under reduced pressure, and the same volume of anhydrous acetonitrile was added to dissolve it. Then oxygen was added to the reaction solution and continued to λ≥400nm- After the reaction is irradiated with light at 760nm, column chromatography can obtain the biphenyl ten-membered ring dilactone compound. The reaction equation is shown in the following formula.
[0040]
[0041] The olefin cyclopropylidene cyclopropane was used in Example 1 to obtain biphenyl ten-membered ring dilactone 3a, white powder; m.p.192-194℃; 1 H NMR(300MHz, CDCl 3 ): δ 7.58-7.36 (m, 8H), 1.78-1.69 (m, 2H), 1.44-1.35 (m, 2H), 0.99-0.90 (m, 2H), 0.28-0.19 (m, 2H) ppm; 13 C NMR(75MHz, CDCl 3 ): δ170.0(2C), 137.9(2C), 133.7(2C), 131.1(2C), 131.0(2C), 127.8(...
Embodiment 2
[0058] 1,10-phenanthroline-5,6-dione (PN) and 2 times the molar amount of olefin are dissolved in anhydrous acetonitrile (PN concentration is 0.02M). Reaction under light (400nm-760nm) conditions, the reaction is detected by TLC, after the PN is consumed, oxygen is supplied to the reaction solution and irradiated with λ≥300nm-760nm light. After the reaction is over, column chromatography can obtain the coupling For pyrido ten-membered ring dilactone compounds, the reaction equation is shown in the following formula.
[0059]
[0060] The olefin cyclopropylidene cyclopropane was used in Example 2 to obtain bipyrido ten-membered ring dilactone 5a, white powder; m.p.254-256℃; 1 H NMR(300MHz, CDCl 3 ): δ8.93 (d, J = 3.6 Hz, 2H), 7.83 (d, J = 7.5 Hz, 2H), 7.41 (dd, J = 7.5, 4.8 Hz, 2H), 1.78-1.65 (m, 2H) , 1.45-1.33 (m, 2H), 1.03-0.94 (m, 2H), 0.33-0.24 (m, 2H) ppm; 13 C NMR(75MHz, CDCl 3 ): δ168.6, 153.6, 152.0, 134.4, 130.3, 123.0, 64.5, 14.1, 6.7ppm; IR(KBr)v max / cm -1 : 1759, ...
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Abstract
The invention relates to a dibenzyl-macrolide compound based on photoreaction and a synthesis method thereof. The synthesis method comprises the following steps: dissolving dibenzyl-ortho-dicarbonyl compounds and olefins in anhydrousbenzene or anhydrousacetonitrile, and reacting under the illumination of 400-760nm continuous light; monitoring the reaction process by TLC (thin layerchromatography); after the all dibenzyl-ortho-dicarbonyl compounds are converted into the intermediate product 2,3-dihydro-1,4-dioxin compounds, evaporating to remove the benzene under reduced pressure; dissolving by adding anhydrousacetonitrile, wherein if the previous solvent is acetonitrile, the step can be omitted; while introducing oxygen, illuminating the solution with continuous light of which the wavelength is 400-760nm or 300-760nm; and monitoring the reaction process by TLC, carrying out column chromatography after the reaction finishes, thereby obtaining the dibenzyl-macrolide compound. The method is simple to operate, the atom utilization ratio is up to 100%, and the raw materials are cheap and have high synthesis value.
Description
Technical field [0001] The present invention relates to a biaryl and midring lactone compound in the field of chemical synthesis and a synthesis method thereof. Background technique [0002] Biaryl mesoprolactones such as biphenyl mesoprolactone are the core building blocks of many biologically active natural products, such as the ellagitannin family. However, the complexes formed by bipyridine compounds coordinated with metals have many applications in catalysis, and the catalytic activity of the extended bipyridomid cyclic lactones coordinated with metals is also worth studying. Therefore, the method of effectively constructing this type of biaryl and midring lactone is of great significance. [0003] Because of the twist of the two aryl planes in the biaryl and midcyclic lactone, its synthesis is very difficult. In the existing reports, there are only a few methods to synthesize biaryl and mesoprolactone. Earlier, Toshiyuki Itoh and Giuseppe Capozzi et al. reported the prepar...
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