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Chiral helicene with binaphthol structure and preparation method of chiral helicene

A technology of binaphthol and chirality, which is applied in the field of design and synthesis of chiral catalysts, can solve the problems of complex and expensive synthetic routes of precursor compounds, unfavorable preparation and application of chiral helicene, etc., and achieve good asymmetric catalysis or non- Symmetrical recognition effect, correct structure, and short synthesis route

Inactive Publication Date: 2018-05-25
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method requires the use of expensive metal catalysts, and the synthesis route of precursor compounds is complicated, which is not conducive to the large-scale preparation and application of chiral helicenes.

Method used

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  • Chiral helicene with binaphthol structure and preparation method of chiral helicene
  • Chiral helicene with binaphthol structure and preparation method of chiral helicene
  • Chiral helicene with binaphthol structure and preparation method of chiral helicene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Example 1: Preparation of 5-(2-(methoxymethoxy)naphthalene-1-yl)-6-methoxymethoxy-15-bromo[6]helicene

[0031] a. Synthesis of intermediate 3-(4-(4-bromostyryl) styryl)-2,2'-bis(methoxymethoxy)-1,1'-binaphthalene

[0032]

[0033] 0.2g (R)-2,2'-bis(methoxymethoxy)-[1,1'-binaphthyl]-3-aldehyde and 0.32g (E)-(4-(4-bromobenzene Vinyl)benzyl)triphenylphosphine bromide (1.05eq.) was added to 15mL of dry THF, and sodium tert-butoxide (1.5eq.) was added in batches under ice-bath conditions, and the solution turned orange-red. Stir in an ice bath, and after half an hour, stir at room temperature until the reaction is complete. 20 mL of water was added to the reaction solution to quench the reaction, the aqueous phase was extracted with 20 mL of dichloromethane, the organic phase was washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate, and the solvent was spun off to obtain a yellow solid with a yield of 89%.

[0034] b, the synthesis of target 5-(2-(m...

Embodiment 2

[0051] Example 2: 6,13-bis(methoxymethoxy)-5,14-bis(2-(methoxymethoxy)naphthalen-1-yl)-9-bromo-[7]helicene preparation of

[0052] a. Intermediate 1,4-bis(2-(2,2'-bis(methoxymethoxy)-[1,1'-binaphthyl]-3-yl)vinyl)-2-bromobenzene Synthesis

[0053]

[0054] 0.3g (R)-2,2'-bis(methoxymethoxy)-[1,1'-binaphthyl]-3-aldehyde and 0.35g ((2-bromo-1,4-phenylene (yl)bis(methylene))bistriphenylphosphine bromide (0.55 eq.) was added to 15 mL of dry THF. Under ice-cooling, sodium tert-butoxide (2.5eq.) was added in batches, and the solution turned orange-red. Under ice bath, stir for half an hour, rise to room temperature and stir until the reaction is complete. 20 mL of water was added to the reaction solution to quench the reaction, the aqueous phase was extracted with 20 mL of dichloromethane, the organic phase was washed with 20 mL of saturated brine, dried over anhydrous sodium sulfate, and the solvent was spun off to obtain a yellow solid with a yield of 91%.

[0055] b. Synthe...

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Abstract

The invention discloses a chiral helicene with a binaphthol structure, and further provides a preparation method of the chiral helicene. According to the method, chiral binaphthol aldehyde is used asa raw material, and the chiral helicene is synthesized by alkene and photocatalysis ring closure. The chiral helicene with the binaphthol structure has the advantages that the raw material is easily obtained, a synthesizing method is simple, a synthesizing route is short and the like. The obtained chiral helicene compound can be applied to the field of asymmetric catalysis or chiral recognition.

Description

【Technical field】 [0001] The invention relates to a chiral helicene with a binaphthol structure and a preparation method thereof, belonging to the field of design and synthesis of chiral catalysts. 【Background technique】 [0002] Helicenes are a class of molecules formed by ortho-fused benzene rings. Helicene has a unique helical structure and chiral optical properties, and is used in asymmetric catalysis (Angew. ), self-assembly (Angew.Chem., Int.Ed., 2009, 48, 7837), nonlinear optical materials (Science, 1998, 282, 913), chiral optical materials (J.Am.Chem.Soc., 2014, 136, 10826; J.Am.Chem.Soc., 2014, 136, 13045) and other fields have a wide range of applications. At present, the preparation of chiral helicene mainly depends on the separation of racemic helicene samples by chiral chromatographic columns, and there are relatively few synthetic methods for directly preparing chiral helicene. It is reported in the literature that a chiral alkyne compound (Angew.Chem., Int....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C41/18C07C41/30C07C43/225C07C37/06C07C39/40B01J31/02C07B53/00
CPCC07B53/00C07C37/06C07C39/40C07C41/18C07C41/30C07C43/225B01J31/0232C07B2200/07
Inventor 陈绍晋胡志强王鲲鹏葛兆海吕承东张文轩
Owner QINGDAO UNIV OF SCI & TECH
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