Dioxa [5] helicene compound as well as preparation method and application thereof

A technology of dioxa, compounds, applied in the field of preparation of dioxa[5] helicene compounds, can solve the problems such as difficult synthesis and research of oxa helixes, and achieve a wide range of substrates, good application prospects, and reaction The effect of mild conditions

Pending Publication Date: 2022-01-11
SHENZHEN RES INST THE CHINESE UNIV OF HONG KONG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of this application is to provide a dioxa[5]helicene compound and its preparation method and application, aiming to solve the technical problems that are difficult to synthesize and study oxahelicones to a certain extent

Method used

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  • Dioxa [5] helicene compound as well as preparation method and application thereof
  • Dioxa [5] helicene compound as well as preparation method and application thereof
  • Dioxa [5] helicene compound as well as preparation method and application thereof

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preparation example Construction

[0046] The second aspect of the embodiment of the present application provides a method for preparing a dioxa[5]helicene compound, comprising the following steps:

[0047] In a protective atmosphere, the reactant shown in the following formula II and the base are heat-treated in an organic solvent for reaction to generate a dioxa[5]penthexene compound shown in the following formula I:

[0048]

[0049] Among them, R 1 , R 2 hydrogen atom, C 1 -C 10 Any one of alkyl, alkoxy, phenyl, halogen atom, trifluoromethyl, cyano, aldehyde, ketone, carboxylic acid, carboxylic acid derivative functional group, pyridyl, or other aromatic hydrocarbon functional groups species; R 3 is an aryl or nitrogen heterocycle.

[0050] It should be noted that the above reaction can obtain the product under a general air atmosphere, and it can also be reacted under a protective gas. The protective atmosphere is nitrogen, argon or other inert gases that do not react with the reactants, which can ...

Embodiment 1

[0085] Add the starting material IIa, namely 2-(2-benzylnaphtho[2,1-b]furan-1-yl)-4-methylphenyl triflate (0.3mmol) into a sealed reaction tube, nitrogen After replacing three times, add dry dimethylformamide (3 ml) to dissolve, then add dried 1,8-diazabicyclo[5.4.0]undec-7-ene (2.5equiv.), The reaction tube was placed in an oil bath at 100° C. for 3 hours. After the reaction was completed, the reaction was stopped, and 5 ml of water and 5 ml of ether were added to the system. Add 5 ml of water and 5 ml of ether for extraction three times, combine the organic phases, dry over anhydrous sodium sulfate, and remove the ether by rotary evaporation under reduced pressure to obtain the initial product, which is purified by column chromatography to obtain dioxa[5] Helicene compounds Ia.

[0086] As shown in Table 1, the raw material II of this example is marked as IIa, the product I is marked as Ia, and the product Ia is specifically 2,-methyl-6-phenyl-6H-naphthol[1',2':4 ,5] Furo[...

Embodiment 2

[0089] The raw material IIa, namely 2-(2-benzylnaphth[2,1-b]furan-1-yl)-4-methylphenyl trifluoromethanesulfonate (0.3mmol) and dried molecular sieves ( 0.15 gram) is added in the sealed reaction tube, and all the other steps and raw material proportioning are with embodiment 1.

[0090] As shown in Table 1, the raw material II of this example is marked as IIa, the product I is marked as Ia, and the product Ia is specifically 2,-methyl-6-phenyl-6H-naphthol[1',2':4 ,5] Furo[2,3-c]benzopyran, the yield was 92%.

[0091] Proton NMR spectrum of product Ia: 1 H NMR (500MHz, CDCl 3 ): δ=8.82(d, J=8.5Hz, 1H), 8.01(d, J=8.0Hz, 2H), 7.78(d, J=9.0Hz, 1H), 7.68(t, J=7.5Hz, 1H ),7.65(d,J=9.0Hz,1H),7.57(t,J=7.5Hz,1H),7.51-7.49(m,2H),7.43-7.40(m,3H),7.06(s,1H) ,6.43(s,1H),2.48(s,3H).

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Abstract

The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a preparation method of a dioxa [5] helicene compound and an application thereof, and the dioxa[5]helicene compound provided by the invention has good potential application prospects in the fields of photoelectric functional materials, asymmetric synthesis application, metal catalysis and the like. The raw materials adopted in the preparation method are cheap, easy to obtain and diversified, the high-yield dioxa [5] pentahelicene compound can be obtained through reaction under the action of alkali which is easy to obtain commercially, operation is easy, reaction conditions are mild, existence of different functional groups can be compatible, the substrate application range is wide, the product yield is high, and the defect that expensive and unavailable raw materials are used in a traditional transition metal catalytic synthesis method is overcome.

Description

technical field [0001] The application belongs to the technical field of organic chemical synthesis, and in particular relates to the preparation method and application of dioxa[5]helicene compounds. Background technique [0002] Helical hydrocarbons are a class of macromolecules that widely exist in nature. For example, DNA and protein biomacromolecules that are closely related to life activities all have a helical conformation, and dioxa[5]helicene compounds are one of the dioxygen-containing Helical hydrocarbons. In the past one hundred years, helical hydrocarbons with different ring numbers have been widely reported and displayed before people's eyes, because these high polymers with helical conformation have unique properties and potential application values. This non-planar, helical hydrocarbon exhibits special structural, optical, and electronic properties. The original helical hydrocarbons are carbon helical hydrocarbons, which refer to a skeleton composed of all c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 邝福儿刘天艺蔡佩盈
Owner SHENZHEN RES INST THE CHINESE UNIV OF HONG KONG
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