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Chiral (R)-triaryl methane derivative with substituted diphenyl and 3-indolyl framework and synthesis method of derivative
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A technology for triarylmethane and a synthesis method, which is applied in the field of chiral-triarylmethane derivatives and the synthesis thereof, can solve the problems of synthesis methods and complex processes without chiral triarylmethane derivatives, and achieves wide application range, mild Reaction conditions, the effect of high yield
Inactive Publication Date: 2019-08-23
XUZHOU NORMAL UNIVERSITY
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At present, the methods for synthesizing triarylmethane mainly include: Friedel-Crafts alkylation reaction, coupling reaction, reduction reaction, etc., most of which require complex processes and harsh conditions, and there is no information on chiral triarylmethane derivatives at home and abroad. Related reports on synthetic methods
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Embodiment 1
[0027] Embodiment 1: in 2 milliliters of acetones, add the compound of formula 1a of 0.12 millimoles and the compound of formula 2a of 0.1 millimoles as reactant, 100 milligrams of magnesium sulfates as additive, the chiral phosphoric acid of 0.01 millimoles (being formula 4 compounds) as Catalyst, reacted at -30 ℃ for 12 hours, TLC followed the reaction to the end, filtered to remove magnesiumsulfate, washed the filter cake with ethyl acetate, and the obtained filtrate was concentrated and then passed through silica gelcolumn chromatography (eluent was petroleumether and ethyl acetateMixed solution with a volume ratio of 8:1) to obtain the chiral (R) triarylmethane derivative 3aa as a white solid.
[0028] The structural characterization data of product 3aa in Example 1 are as follows:
[0029] 1 H NMR (400MHz, CDCl 3 )δ8.01(s,1H),7.38–7.29(m,2H),7.23–7.13(m, 2H),7.11(s,2H),7.06–7.00(m,2H),6.90–6.82(m, 2H),6.72–6.66(m,1H),5.70(s,1H),5.41–5.15(m,1H),5.15(s,1H),1.38(s,18...
Embodiment 17
[0038] Embodiment 17: In 2 milliliters of acetone, add 0.12 millimoles of formula 1a compound and 0.1 millimoles of formula 2b compound as reactant, 100 milligrams of magnesium sulfates as additive, 0.01 millimoles of chiral phosphoric acid (i.e. formula 4 compound) as Catalyst, reacted at -30 ° C for 12 hours, TLC followed the reaction to the end, filtered to remove magnesium sulfate, washed the filter cake with ethyl acetate, and separated the obtained filtrate through silica gelcolumn chromatography to obtain chiral (R) triaryl Methane derivative 3ab, white solid.
[0039] The structural characterization data of product 3ab in Example 17 are as follows:
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Abstract
The invention discloses a chiral (R)-triaryl methane derivative with substituted diphenyl and a 3-indolyl framework and a synthesis method of the derivative. The chiral (R)-triaryl methane derivativehas a chemical structure formula (3) shown in the specification. The synthesis method comprises the following steps: by taking the compound of a formula 1 and the compound of a formula 2 as reaction raw materials, and acetone as a solvent, adding magnesiumsulfate, carrying out stirring to implement reactions under the action of a chiral phosphoric acid catalyst, carrying out TLC (thin-layer chromatography) reaction tracking till the reactions are completed, and carrying out filtration, concentration, and purification, so as to obtainthe derivative, wherein the reaction mole ratio of the compound of the formula 1 to the compound of the formula 2 is 2:1 to 1.2:1; and the reaction temperature is minus 30 DEG C to 0 DEG C. The derivative is not only capable of achieving diversity and complexity of product molecules, high enantioselectivity, high atom economy, environmental-friendliness and wide application ranges at one step, but also easy in raw material obtaining, simple and safe in operation, gentle in reaction condition, short in reaction time and simple in aftertreatment, and thus has great application values and potential social and economic benefits.
Description
technical field [0001] The invention belongs to the field of organic synthetic chemistry and relates to the synthesis of a triaryl methane derivative, in particular to a chiral (R)-triaryl methane derivative containing a substituted diphenyl and 3-indolyl skeleton and its synthesis method. Background technique [0002] There are many chiral compounds in nature, and these chiral compounds have two enantiomers that are mirror images of each other. When a chiral compound enters a living body, its two enantiomers usually exhibit different biological activities. With chiral drugs, one isomer may be effective, while the other may be ineffective or even harmful. Chiral pharmacy uses this principle of compounds to develop drugs with high efficacy and few side effects. In terms of clinical treatment, taking enantiomerically pure chiral drugs can not only eliminate the toxic and side effects caused by ineffective (bad) enantiomers, but also reduce the dosage and the metabolic burde...
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