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A class of molecular cage compound and its preparation method and application
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A technology of compounds and molecular cages, applied in silver organic compounds, chemical instruments and methods, active ingredients of hydroxyl compounds, etc., to achieve the effects of improving solubility, great application prospects, and improving chemical stability
Active Publication Date: 2021-06-25
INST OF CHEM CHINESE ACAD OF SCI +1
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Embodiment 1
[0118] Synthesis of Cylindrical Molecular Cage Compound (1A) Based on 1,3,5,7,9-pentapyridinecorannene and Its Application in the Recognition and Release of Adamantane and Its Derivatives
[0119] 1.1 Preparation of compound (1A)
[0120]
[0121]1) Compound 5-bromo-3-hydroxypyridine (2.00g, 11.5mmol) was dissolved in DMF solution (15mL), and K 2 CO 3 (1.91g, 13.8mmol) and triethylene glycolmonomethyl ether benzenesulfonate (4.02g, 12.65mmol), pumped and evacuated 3 times and filled with argon protection, the mixture was heated to 70°C and stirred overnight. After the reaction was finished, it was extracted with ethyl acetate, washed successively with 2M sodiumhydroxide solution and deionized water, the organic phase was dried with anhydroussodiumsulfate, filtered, and purified by silica gelchromatography column after vacuum distillation (eluent: DCM / Acetone =200 / 1~50 / 1), a light yellow oil (compound (9A)) was finally obtained with a yield of about 90%. 1 H-NMR (400...
Embodiment 2
[0132] Synthesis of Oblate Spherical Molecular Cage Compound (2A) Based on 1,3,5,7,9-Pententpyridylcorannene and Its Application in the Recognition and Release of Adamantane and Its Derivatives
[0133] 2.1 Preparation of molecular cage compound (2A)
[0134]
[0135]1) To a solution of 2-bromo-5-hydroxypyridine (3.0 g, 17.24 mmol) in DMF (15 mL) was added 1-iodo-2-methylpropane (2.2 mL, 18.96 mmol) and K 2 CO 3 (3.57 g, 25.86 mmol). The suspension was stirred overnight at 60°C, then poured into pure water, followed by extraction with ethyl acetate. The organic layer was washed 5 times with saturated brine to remove contained DMF, dried over sodiumsulfate and concentrated in vacuo. The residue was purified on silica gel flash column chromatography (ethyl acetate / hexane, 1:15) to obtain light yellow oil (compound (11A)) (1.98 g, yield: 50%). 1 H NMR (400MHz, CDCl 3 )δ=8.03(dd, J=9.3, 2.9Hz, 1H), 7.35(d, J=8.7Hz, 1H), 7.08(dd, J=8.7, 3.1Hz, 1H), 3.74(d, J=6.5 Hz, 2H), ...
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Abstract
The invention belongs to the technical field of supramolecular materials, and in particular relates to a class of molecular cage compounds and a preparation method and application thereof. The molecular cage compound of the present invention can significantly improve the solubility of the cage compound in organic solvents or even water; the molecular cage compound of the present invention has a space size matched with adamantane and its derivatives, and can be some unstable adamantane Derivatives provide a closed space to improve their chemical stability; the molecular cage compound of the present invention can selectively complex adamantane and its derivatives, and at the same time release quantitatively under specific conditions, and realize efficient recovery of host molecules , which has great application prospects in the field of drug delivery and release.
Description
technical field [0001] The invention belongs to the technical field of supramolecular materials, and in particular relates to a class of molecular cage compounds and a preparation method and application thereof. Background technique [0002] The function of the molecular cage is to create an internal environment that is selectively open to the outside, and at the same time play an important role in the storage of matter and energy, as well as the catalysis, replication and sensing that occur in the molecular cage. With the help of adjustable hydrogen bonds, metal-organic coordination bonds, etc., the self-assembled artificial molecular cages avoid the difficult multiple loop closure problems faced by the synthesis of artificial molecular cages based on covalent bonds. At the same time, the shape of the internal cavity of the cage, The size is easily adjustable by cleverly designing self-assembling units. Since Dalcanalc reported for the first time that acetonitrile-based fu...
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