Indole compound and application thereof

A technology of indole compounds and compounds, which is applied in the field of indole compounds and their application in the preparation of lenses, can solve the problems of inconspicuous anti-blue light effects, reduced light transmittance, and high production costs, achieving significant anti-blue light, adding The effect of reducing the amount of the effect is remarkable

Active Publication Date: 2022-02-11
SHANGHAI GANTIAN OPTICAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among these absorbents, toners have the defects of deep background color, low light transmittance, which significantly affect people's daily use; while nano-inorganic materials have the problems of complicated manufacturing process and high preparation cost; the remaining types of absorbents are There is a disadvantage that the anti-blue light effect is not obvious

Method used

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  • Indole compound and application thereof
  • Indole compound and application thereof
  • Indole compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]

[0043] In the first step, the compound (15.9 g, 0.1 mol) shown in dry formula (II) and bromoethane (10.9 g, 0.1 mol) were dissolved in 230 mL of anhydrous tetrahydrofuran, added to a dry four-necked flask, and stirred at room temperature 2h, the reaction solution was poured into a large amount of water, extracted with dichloromethane (100mL), washed five times with water (5×100mL), the organic phases were combined, and washed with Na 2 SO 4 After drying, filtering, the organic phase was spin-dried, and separated by column chromatography, using 2 / 8 ethyl acetate / n-hexane as eluent to obtain off-white solid product (IIIa). NMR showed that the product had a structure consistent with 4-ethyl-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole. HRMS(ESI,m / z):[M+H] + calcd for (C 13 h 17N), 188.1434; found, 188.1336.

[0044]

[0045] In the second step, in a 500mL three-neck flask, drop into the compound (Ⅲa) (18.7g, 0.1mol) prepared in the first step, phosphorus oxychlo...

Embodiment 2

[0051]

[0052] In the first step, the compound (15.9 g, 0.1 mol) shown in dry formula (II) and p-bromoanisole (18.7 g, 0.1 mol) were dissolved in 230 mL of anhydrous tetrahydrofuran, and added to a dry four-necked flask, Stir at room temperature for 2h, pour the reaction solution into a large amount of water, extract with dichloromethane (100mL), wash with water five times (5×100mL), combine the organic phases, wash with Na 2 SO 4 After drying, filtering, and spin-drying the organic phase, an oily product (IIIb) was obtained for the next reaction. NMR showed that the product had a structure consistent with 4-(4-methoxyphenyl)-1,2,3,3a,4,8b-hexahydrocyclopenta[b]indole. HRMS(ESI,m / z):[M+H] + calcd for (C 18 h 19 NO), 266.1539; found, 266.1579.

[0053]

[0054] In the second step, in a 500mL three-neck flask, drop into the compound (Ⅲb) (26.5g, 0.1mol) prepared in the first step, phosphorus oxychloride (3.06g, 0.02mmol), DMF (73g, 1.0mol), at room temperature After...

Embodiment 3

[0061]

[0062] The bromoethane used in the first step reaction in Example 1 was replaced with bromoisopropane, and other steps and reagents used were the same as in Example 1 to obtain compound I-3. 1 H NMR (500MHz, CDCl 3 )δ8.23(S,1H)6.68-7.14(m,3H),3.39-4.33(q,3H),2.74-3.02(t,2H),1.12-1.93(m,15H).HRMS(ESI,m / z):[M+H] + calcd for (C 20 h 24 N 2 o 2 ), 325.1911; found, 325.1945.

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Abstract

The invention discloses an indole compound, which has the following structural general formula: in the formula, R1 is selected from hydrogen, C1-C8 straight-chain alkyl and C1-C8 branched-chain-containing alkyl, and R3 is selected from hydrogen, methyl, ethyl, methoxyl and ethoxyl; and R2 is selected from hydrogen, C1-C8 straight chain alkyl and C1-C8 alkyl containing branched chains. An anti-blue-light substrate lens adopts the indole compound, the anti-blue-light effect is remarkable, the addition amount of the blue-light absorbent is greatly reduced, and various physical properties of the lens are basically not affected.

Description

technical field [0001] The invention belongs to the technical field of lens materials, and in particular relates to an indole compound and its application in lens preparation. Background technique [0002] After 2010, smart phones, tablets, computers, etc. have gradually entered people's lives, and various mobile phone APPs have taken up a lot of people's fragmented time, and this change will place a huge burden on people's eyes. Generally speaking, the screens of electronic devices will continue to emit harmful blue light radiation, and the high-energy short-wave blue light with a wavelength between 380 and 450nm has a risk of permanent damage to the retina. This kind of blue light radiation has a strong penetrating power, can penetrate the lens directly to the retina, cause retinal macular degeneration, aggravate chromatic aberration and blurred vision, and finally destroy the balance of hormone secretion and affect vision and sleep quality, followed by various diseases P...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/94G02B5/22
CPCC07D209/94G02B5/223
Inventor 宋熊荣甘家安王卓尤韦霖甘祖辉杨德鹏
Owner SHANGHAI GANTIAN OPTICAL MATERIALS
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