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Spiro-condensed tricyclic spirooxazine photochromic compound and preparation method thereof

A photochromic, spirooxazine technology, applied in chemical instruments and methods, color-changing fluorescent materials, organic chemistry, etc., can solve problems such as increasing the cost of material synthesis, limiting the yield of target products, and inability to further improve, and achieve good light. The effect of chromogenic properties, good fatigue resistance and strong practicability

Active Publication Date: 2017-06-13
TIANJIN UVOS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But there are following problems: the one, the market price of the intermediates with this group is usually all higher; the second is to adopt the combination of intermediates with these groups to carry out the condensation reaction yield will also be affected by its own characteristics, Target product yields are often limited and cannot be further increased
These factors have greatly increased the synthesis cost of materials, which is very unfavorable to market applications.

Method used

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  • Spiro-condensed tricyclic spirooxazine photochromic compound and preparation method thereof
  • Spiro-condensed tricyclic spirooxazine photochromic compound and preparation method thereof
  • Spiro-condensed tricyclic spirooxazine photochromic compound and preparation method thereof

Examples

Experimental program
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Effect test

preparation example Construction

[0042] Preparation of Intermediates:

[0043] Synthesis of intermediate 1--nitroso--2-naphthol copper complex (copper salt)

[0044] Under stirring, the dissolved 13.6g CuCl 2 400ml of aqueous solution was added dropwise to 800ml of a mixed solution of tetrahydrofuran and water dissolved with 39.8g of 1-nitroso-2-naphthol at a volume ratio of 1:1. After stirring for 20 minutes, vacuum filtration, washing with water, and drying gave 39.1 g of the product with a yield of 96%.

[0045] Synthesis of Intermediate Substituted 2,3,3--Trimethylindoline

[0046] In a 250ml three-necked flask, add 1.62mmol p-methoxyphenylhydrazine hydrochloride and 100ml glacial acetic acid, heat to reflux, slowly add 1.62mmol methyl isopropyl ketone dropwise, after the dropwise, continue to reflux for 10 hours. Stop the reaction, cool to room temperature with Na2 CO 3 The saturated solution was neutralized to neutral or slightly alkaline, extracted with dichloromethane, dried over anhydrous magnesi...

Embodiment 1

[0050] Target product: 5--chloro--1,2'--(1,2--ethyleneoxy)--1,3,3--trimethyl--6'--piperidinyl--spiro [2,3'--[3H]--naphtho[2,1--b][1,4]oxazine]

[0051] In a 250ml three-necked flask, add 1.0mmol of copper salt 1 and 4.0mmol of piperidine, use 50ml of anhydrous methanol as a solvent, and heat to reflux for 4h. in N 2 Under protection, 30 ml of anhydrous methanol solution containing 1.8 mmol 5-chloro N-(2-hydroxyethyl) 2,3,3-trimethylindoline bromide and 4 ml triethylamine were added dropwise, Continue the reflux reaction for 8h, TCL monitoring, stop the reaction and cool to room temperature, concentrate under reduced pressure, use petroleum ether / ethyl acetate (5:1) as eluent to carry out column chromatography to obtain a light yellow solid with a yield of 24 %.

[0052] m.p.226-228℃. 1 H NMR (400MHz, CDCl 3 )8.42(d, J=8.0Hz, 1H, Ar-H), 8.11(d, J=8.4Hz, 1H, Ar-H), 7.51-7.55(m, 1H, Ar-H), 7.40-7.44( m,1H Ar-H,),7.20(dd,J 1 =2.4Hz,J 2 =8.4Hz,1H,Ar-H),6.97(d,J=2.0Hz,1H,Ar-...

Embodiment 2

[0057] Target product: 5--chloro--1,2'--(1,2--ethyleneoxy)--1,3,3--trimethyl--6'--morpholinyl--spiro [2,3'--[3H]--naphtho[2,1--b][1,4]oxazine]

[0058] In a 250ml three-necked flask, add 1.0mmol of copper salt and 4.0mmol of morpholine, use 50ml of anhydrous methanol as a solvent, and heat to reflux for 4h. in N 2 Under protection, 30 ml of anhydrous methanol solution containing 1.8 mmol 5-chloro N-(2-hydroxyethyl) 2,3,3-trimethylindoline bromide and 4 ml triethylamine were added dropwise, The reflux reaction was continued for 8 h, TCL monitored until the reactant point disappeared, the reaction was stopped and cooled to room temperature, concentrated under reduced pressure, and column chromatography was performed using petroleum ether / ethyl acetate (3:1) as eluent to obtain a white solid. The yield was 20%. m.p.184-186℃ 1 H NMR (400MHz, CDCl 3 ) 8.17 (d, J = 8.4Hz, 1H, Ar-H), 7.63 (d, J = 8.4Hz, 1H, Ar-H), 7.44-7.47 (m, 1H, Ar-H), 7.32-7.36 ( m,1H,Ar-H),7.14(dd,J 1 =2....

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Abstract

The invention provides a spiral-thick tricyclic spirooxazine photochromic compound and a preparation method thereof. An intermediate is simple and easy to obtain, synthesis steps are simple and convenient, and the obtained photochromic compound has high photosensitivity, high fatigue resistance and high chroma. The structural formula of the spiral-thick tricyclic spirooxazine photochromic compound is as shown in the specification.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a photochromic compound and a preparation method thereof. Background technique [0002] As an important class of molecular optical switch materials, spirooxazine photochromic compounds are widely used in optical filters, molecular optical switches, camouflage, Clothing, anti-counterfeiting, and optical record storage have important application values, and have been marketed in some fields. In order to obtain photochromic compounds with better performance, the design and synthesis of spirooxazine photochromic compounds has always been a research hotspot in the field of this type of compounds, for example, to further improve the application characteristics of materials such as light resistance and weather resistance, and to improve the hue The application characteristics of aspects are the two main directions of research in this field. [0003] At present, the development of the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K9/02C07D498/20
Inventor 孟继本李红庞美丽吴边鹏边俊民翟言
Owner TIANJIN UVOS TECH CO LTD
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