Acyl-substituted triptycene and preparation method thereof

A technology of acyl-substituted triptycene, which is applied in the field of acyl-substituted triptycene and its preparation, can solve the problems of many synthesis steps, complex reagents, and high operation requirements, and achieve simple synthesis, cheap raw materials, and high product yield. Effect

Inactive Publication Date: 2012-06-13
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the above methods all have many synthetic step

Method used

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  • Acyl-substituted triptycene and preparation method thereof
  • Acyl-substituted triptycene and preparation method thereof
  • Acyl-substituted triptycene and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Example 1, preparation of trans diformyl triptycene and cis diformyl triptycene

[0046]

[0047] 3.2g (12.6mmol) triptycene, 10.1g (75.5mol) aluminum trichloride, 5.7mL (63mmol) 1,1'-dichloromethyl methyl ether and 100mL 1,1 ', 2,2'-Tetrachloroethane, react in ice bath (0°C) for 11 hours, add 100mL dilute hydrochloric acid (2M), stir at room temperature for 1 hour until the solution is clear, add dichloromethane for extraction, take the organic layer and wash it with MgSO 4 Drying, filtering, spin-drying, using dichloromethane / ethyl acetate=80:1 (v / v) as the developing solvent for flash column chromatography separation, wherein trans diformyl triptycene R f =0.55, cis-diformyl triptycene R f =0.43, 1.4 g of trans diformyl triptylene and 1.7 g of cis diformyl triptylene were obtained, with a total yield of 80%.

[0048] The structural identification results of trans-diformyl triptycene are as follows:

[0049] 1 H NMR (300MHz, CDCl 3 ): δ9.88(s, 2H), 7.90(s, 2H)...

Embodiment 2

[0053] Example 2, preparation of trans diacetyl triptycene and cis diacetyl triptycene

[0054]

[0055] Add 1.15g (4.5mmol) triptycene, 3.62g (27mmol) aluminum trichloride, 1.60mL (22.6mmol) acetyl chloride and 50mL 1,1',2,2'-tetrachloro Ethane, react in ice bath (0°C) for 11 hours, add 50mL dilute hydrochloric acid (2M), stir at room temperature for 1 hour until the solution is clear, add dichloromethane for extraction, take the organic layer and wash it with MgSO 4 Dry, filter, spin-dry, and use dichloromethane / ethyl acetate=60:1 (v / v) as developing solvent to carry out column flash column chromatography, wherein trans-diformyl triptycene R f =0.6, cis-diformyl triptycene R f =0.5, 0.53 g of trans diacetyl triptycene and 0.46 g of cis diacetyl triptyl were obtained, with a total yield of 65%;

[0056] The structural identification results of trans-diacetyl triptycene are as follows:

[0057] 1 H NMR (300MHz, CDCl 3 )δ8.00(d, J=1.4Hz, 2H), 7.64(dd, J=7.7, 1.6Hz, 2H),...

Embodiment 3

[0061] Example 3, preparation of trans-triacetyl triptycene and cis-triacetyl triptycene

[0062]

[0063] Add 0.76g (3mmol) triptycene, 4.78g (36mmol) aluminum trichloride, 2.1mL (30mmol) acetyl chloride and 25mL 1,1',2,2'-tetrachloroethane to a 50mL round bottom flask successively , react in an ice bath (0°C) for 21 hours, add 25 mL of dilute hydrochloric acid (2M), stir at room temperature for 1 hour until the solution is clear, add dichloromethane for extraction, take the organic layer and wash it with MgSO 4 Dry, filter, spin dry, and use dichloromethane / ethyl acetate=20:1 (v / v) as developing solvent to carry out column flash column chromatography to separate trans-diformyl triptycene R f =0.33, cis-diformyl triptycene R f =0.21, 0.65 g of trans-triacetyl triptycene and 0.18 g of cis-triacetyl triptyl were obtained, with a total yield of 73%.

[0064] The structural identification results of trans-triacetyl triptycene are as follows:

[0065] 1 H NMR (300MHz, CDCl ...

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Abstract

The invention discloses acyl-substituted triptycene and a preparation method thereof. An acyl compound is represented as structural general formula I or II. A framework of the compound is triptycene with a rigid three-dimensional structure. Two or three acyls are selectively introduced on the triptycene framework and can conveniently polymerized into a polymer through McMurry reaction, and the structure of the produced polymer is represented as general formula VI or VII. The preparation method of the acyl-triptycene derivative has the advantages of being cheap in raw materials, simple in synthetization, high in productivity, easy to derivatize and the like. In addition, the produced polymer has good dissolubility, and the acyl-substituted triptycene can be processed conveniently and has wide application prospect.

Description

technical field [0001] The invention relates to an acyl-substituted triptycene and a preparation method thereof. Background technique [0002] Triptycene is a three-dimensional rigid organic molecule. In recent years, triptycene and its derivatives have been widely used in the fields of organic synthesis, supramolecular chemistry, molecular machines, polymer chemistry and medicinal chemistry (Chen, C.-F. Chemical Communications 2011, 47, 1674). As early as 1942, Barlett obtained the triptycene parent compound with a total yield of about 20% by a multi-step reaction (Bartlett, P.D.; Ryan, M.J.; Cohen, S.G. Journal of the American Chemical Society 1942, 64, 2649). In 1958, Wittig et al. developed a preparation method based on the D-A addition reaction of benzyne, so that some derivatized triptycenes could be conveniently prepared (Wittig, G.; Stilz, W.; Knauss, E.Angewandte Chemie 1958, 70, 166). The application of this method in the synthesis of triptycene derivatives is l...

Claims

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Application Information

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IPC IPC(8): C07C47/546C07C49/792C07C45/46C08G61/02
Inventor 陈传峰李鹏飞
Owner INST OF CHEM CHINESE ACAD OF SCI
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