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Method for synthesizing trifluoromethyl substituted dihydrophenanthrene compounds
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A technology of trifluoromethyl and synthesis method, which is applied in the field of synthesis of trifluoromethyl substituted dihydrophenanthrene compounds, can solve problems such as insufficient research and development of dihydrophenanthrene compounds, and achieves reasonable reaction path, high efficiency, Post-processing simple effects
Active Publication Date: 2021-10-19
HENAN NORMAL UNIV
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[0003] At present, the research and development of dihydrophenanthrene compounds is relatively insufficient. Therefore, the development of efficient synthesis methods for trifluoromethyl-substituted dihydrophenanthrene compounds plays an important role in the screening of drug lead compounds
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Embodiment 1
[0041]
[0042] In a 25mL pressure tube, add 2-biphenylboronic acid (0.12mmol, 24mg), 4,4,4-trifluoro-1-(p-tolyl)but-2-en-1-one (0.1mmol, 21.4mg), [Cp tBu RhI 2 ] 2 (0.004mmol, 4.9mg), AgOAc (0.025mmol, 4.2mg), Ag 2 O (0.1mmol, 23.2mg) and EA (1.0mL), the reaction tube was sealed, and then the mixture was heated and stirred at 80°C for 12h. After the reaction is complete, cool to room temperature after the reaction is complete, and spin to dry the solvent. Deionized water and ethyl acetate were added, the aqueous phase was extracted three times, the organic phases were combined, back-extracted once with saturated brine, and dried over anhydroussodiumsulfate. After spin-drying, it was separated by column chromatography (petroleumether / ethyl acetate=15:1) to obtain 3aa (34.2 mg, 94%) as a white solid. The characterization data of this compound are as follows: 1 HNMR (600MHz, CDCl 3)δ7.80–7.73(m,4H),7.34–7.31(m,1H),7.28–7.25(m,1H),7.19(d,J=8.0Hz,2H),7.17–7.08(m,4H) ...
Embodiment 2
[0044] use According to the method described in Example 1, a white solid 3ab (23.0mg, 55%, m.p.114-116°C) was obtained.
[0045] The compound characterization data are as follows: 1 H NMR (400MHz, CDCl 3 )δ7.86(d, J=8.1Hz, 2H), 7.72–7.67(m, 2H), 7.27(d, J=8.0Hz, 2H), 7.18(d, J=8.8Hz, 1H), 7.13( d,J=7.8Hz,1H),6.96(m,2H),5.10(s,1H),3.82(q,J=9.4Hz,1H),2.40(s,3H),2.28(s,3H), 2.27(s,3H). 13 C NMR (100MHz, CDCl 3 )δ196.1, 144.5, 137.7, 137.4, 132.5, 132.3, 131.9, 131.8, 130.5, 130.4, 130.1, 129.8, 129.4, 129.0, 126.4 (q, J = 281.9Hz, 1C), 125.8, 128.7, 123.84, 4, (q, J=27.1Hz, 1C), 21.8, 21.2, 21.1. 19 F NMR (376MHz, CDCl 3 )δ-70.06(d).[M+Na] + Calcd for C 25 h 21 f 3 NaO + 417.1437,Found:417.1437.
Embodiment 3
[0047] use According to the method described in Example 1, a white solid 3ac (29.3mg, 61%, m.p.105-106°C) was obtained.
[0048] The compound characterization data are as follows: 1 H NMR (400MHz, CDCl 3 )δ7.88(d, J=8.1Hz, 2H), 7.77(d, J=8.3Hz, 1H), 7.74(d, J=8.3Hz, 1H), 7.43(dd, J=8.3, 1.9Hz, 1H), 7.35(dd, J=8.2, 1.9Hz, 1H), 7.31(d, J=8.0Hz, 2H), 7.19(s, 1H), 7.13(d, J=1.7Hz, 1H), 5.14( s,1H),3.91(q,J=9.5Hz,1H),2.44(s,3H),1.31(s,9H),1.26(s,9H). 13 C NMR (100MHz, CDCl 3 )δ196.5, 150.8, 150.6, 144.3, 132.9, 132.0, 131.5, 130.0, 129.7, 129.0, 128.3, 126.7, 126.6, 126.5 (q, J = 281.8Hz, 1C), 125.7, 125.6, 123.5, 123.4 (q, , J=26.8Hz, 1C), 46.5, 34.6, 31.4, 31.3, 21.8. 19 F NMR (565MHz, CDCl 3 )δ-70.19(d).[M+Na] + Calcd for C 31 h 33 f 3 NaO + 501.2376, Found: 501.2373.
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Abstract
The invention provides a method for catalytically synthesizing trifluoromethyl substituted dihydrophenanthrene compounds by using transition metal, and belongs to the technical field of organic synthesis. A 2-biphenylboronic acid compound and an alpha, beta-unsaturated ketone compound are used as initial raw materials, and are heated and reacted in an organic solvent under the action of a transition metalrhodium catalyst and a silver salt oxidant to obtain the trifluoromethyl substituted dihydrophenanthrene compounds. In cyclization coupling of 2-biphenylboronic acid and trifluoromethyl substituted ketene, a huge cyclopentadienyl ligand (CptBu) in a catalyst can effectively promote a reduction elimination process before protonation to obtain a [4 + 2] cyclization product instead of a simple 1, 4-addition product, and meanwhile, a bridge ring is separated from coupling of 2-biphenylboronic acid and benzoquinone, which proves that the reaction is subjected to two-step Michael addition again. The method has the advantages of simple and easily-prepared initial raw materials, wide substrate application range, air condition resistance, high yield, simple operation and the like.
Description
technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of trifluoromethyl-substituted dihydrophenanthrene compounds. Background technique [0002] Dihydrophenanthrene compounds can effectively inhibit the production of inflammatory factors by inhibiting NF-κB and other pathways. This type of compound structure exists in a variety of anti-inflammatory drugs, and this type of structure also has good anticancer activity. The trifluoromethyl group is a fluorine-containing group with strong electron-withdrawing property and strong lipophilicity, and the introduction of the trifluoromethyl group can often enhance the drug activity of the drug molecule. [0003] At present, the research and development of dihydrophenanthrene compounds is relatively insufficient. Therefore, the development of efficient synthesis methods for trifluoromethyl-substituted dihydrophenanthrene compounds plays an important role in the s...
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