A type of stilbene compound containing silyl ether and its synthesis method and application

Abstract

A class of silylene compounds containing silylene, which are compounds shown in the following formula I and pharmaceutically acceptable esters or alkyl ethers of compounds shown in formula I. The compounds of the present invention are collagenase inhibitors and can be used for skin aging caused by photoaging. Compared with resveratrol and oxidized resveratrol, the compounds of the present invention use silylene with a stable structure as the basic skeleton, have a more stable structure and a more suitable smell, are more suitable for use as an active ingredient in anti-skin aging skin care products, and have better cosmeceutical skin care effects.

Description

Technical Field

[0001] The invention relates to organic chemistry, and in particular to a class of silylene compounds containing silylene and a synthesis method and application thereof. Background Art

[0002] Anti-aging skin care products contain silicones to enhance the dual effects of vision and sensory perception. More than 40% of skin care products contain silicones, including sunscreen products, face and body care products, and makeup products. Silicones can give skin care products such as lotions, creams and powders a powdery feel and rich texture, making them silky smooth, easy to apply, and reducing stickiness.

[0003] Skin aging is a biological phenomenon involving both intrinsic and extrinsic pathways, and its phenotypic characteristics are rough skin, pigmentation, and decreased elasticity. Intrinsic aging is a process that occurs over time, while extrinsic aging is caused by exposure to environmental factors. Exposure to ultraviolet (UV) light is the most important environmental factor for premature facial aging. UV light can be divided into three types based on wavelength: UVA (320-400nm), UVB (280-320nm), and UVC (200-280nm). UVB is the most active component of sunlight. It causes the production of reactive oxygen species, impairs the antioxidant status of the skin, and causes damage to DNA and proteins. UVB causes direct and indirect photocarcinogenesis and adverse biological effects of photoaging, clinically characterized by wrinkle formation and loss of skin elasticity. UVB-induced degradation of the extracellular matrix (ECM), as well as decreased collagen expression and increased matrix metalloproteinase (MMP) expression, leads to photoaging. Collagen is mainly produced by fibroblasts in the dermis and is the main component of the dermis, which can maintain the structure of the skin and give it toughness and elasticity. The content and distribution of collagen determine whether the skin is young or not. However, an abnormal decrease in collagen content will cause the dermis to become thinner, the skin to sag, lose elasticity, and wrinkles to appear, affecting people's quality of life. With the continuous deepening of collagen research, researchers have found that collagenase plays an important role in the dynamic balance of skin collagen, and its overexpression and abnormal activation are one of the main causes of skin aging. Therefore, inhibiting the activity of collagenase can block the degradation of skin collagen, increase the content of collagen, and achieve anti-aging effects.

[0004] Resveratrol (3,4',5-stilbenetriol; RES) is a natural stilbene polyphenol with three hydroxyl groups that has been shown to have cosmeceutical properties as well as antiproliferative, antioxidant, and anti-inflammatory effects. Oxyresveratrol (4-[(E)-2-(3,5-dihydroxyphenyl)vinyl]benzene-1,3-diol; OXYRES) is a stilbene polyphenol derivative with one RES hydroxyl group found in certain plants and has properties such as potent tyrosinase inhibitory activity. However, RES and OXYRES are photosensitivity and poorly soluble, and are easily oxidized and discolored in solution and produce unpleasant odors. These issues have hindered their use in cosmetics, especially when exposed to light and heat as cosmetic ingredients. Summary of the invention

[0005] The object of the present invention is to provide a class of silylene compounds containing silylene, or cosmeceutical acceptable esters thereof, or alkyl ethers thereof, so as to improve the odor and stability of the compounds and make them more suitable for preparing cosmeceuticals.

[0006] To achieve the above-mentioned purpose, the technical solution of the present invention is as follows:

[0007] A class of silylene compounds containing stilbene, which are compounds represented by the following formula I and pharmaceutically acceptable esters or alkyl ethers of the compounds represented by formula I;

[0008]

[0009] In Formula I: R 1 is selected from hydroxy, fluorine, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, formyloxy, acetyloxy, propionyloxy, butyryloxy, trifluoroacetyloxy, oleate or stearate; R 2 is selected from ethyl, methyl, tert-butyl, isopropyl, propyl, hexyl, phenyl or benzyl; R 3 Selected from hydroxy, fluorine, methoxy, ethoxy, propoxy, butoxy, pentyloxy, hexyloxy, heptyloxy, octyloxy, nonyloxy, decyloxy, formyloxy, acetyloxy, propionyloxy, butyryloxy, trifluoroacetyloxy, oleate or stearate.

[0010] Preferably, the compound is:

[0011] (E)-5-(4-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0012] (E)-5-(5-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0013] (E)-5-(2-hydroxy-6-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0014] (E)-5-(3-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0015] (E)-5-(4-fluoro-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0016] (E)-5-(5-fluoro-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0017] (E)-5-(2-fluoro-6-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0018] (E)-5-(4-methoxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0019] (E)-5-(5-methoxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0020] (E)-5-(2-methoxy-6-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0021] (E)-(2-(3,5-dimethoxyphenylvinyl)-5-methoxyphenoxy)triethylsilyl;

[0022] (E)-(2-(3,5-dimethoxyphenylvinyl)-4-methoxyphenoxy)triethylsilyl;

[0023] (E)-(2-(3,5-dimethoxyphenylvinyl)-3-methoxyphenoxy)triethylsilyl;

[0024] (E)-4-(3,5-dihydroxyphenylvinyl)-3-(triethylsilyloxy)phenyl acetate;

[0025] (E)-3-(3,5-dihydroxyphenylvinyl)-4-(triethylsilyl)phenyl acetate;

[0026] (E)-2-(3,5-dihydroxyphenylvinyl)-3-(triethylsilyloxy)phenyl acetate;

[0027] (E)-5-(4-acetoxy-2-(triethylsilyloxy)phenylvinyl-1,3-benzenediol acetate;

[0028] (E)-5-(5-acetoxy-2-(triethylsilyloxy)phenylvinyl-1,3-benzenediol acetate;

[0029] (E)-4-(3,5-difluorophenylvinyl)-3-(triethylsilyloxy)phenyl acetate;

[0030] (E)-4-(3,5-bis(trifluoromethoxy)phenylvinyl)-3-(triethylsilyloxy)phenyl acetate;

[0031] (E)-5-(4-hydroxy-2-(trimethylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0032] (E)-5-(4-acetoxy-2-(trimethylsilyloxy)phenylvinyl-1,3-benzenediol acetate;

[0033] (E)-5-(2-(dimethylphenylsilyloxy)-4-hydroxyphenylvinyl-1,3-benzenediol;

[0034] (E)-5-(4-acetoxy-2-(dimethylphenylsilyloxy)phenylvinyl-1,3-benzenediol acetate;

[0035] (E)-5-(4-acetoxy-2-(triisopropylphenylsilyloxy)phenylvinyl-1,3-benzenediol acetate;

[0036] (E)-5-(4-hydroxy-2-(triisopropylsilyloxy)phenylvinyl)-1,3-benzenediol;

[0037] (E)-5-(4-acetoxy-2-(benzyldimethylsilyloxy)phenylvinyl-1,3-benzenediol acetate;

[0038] (E)-5-(2-(Benzyldimethylsilyloxy)-4-hydroxyphenylvinyl-1,3-benzenediol.

[0039] The present invention also provides a method for preparing the above compound, comprising:

[0040] The ring-opening silylation of benzofuran is mediated by base to realize the ring-opening silylation of styrene silane, NIC is iodinated to cause silicon group transfer, and then the compound is obtained through coupling reaction.

[0041] The present invention also provides application of the compound in preparing cosmetics.

[0042] Preferably, the cosmetic is an anti-skin aging cosmeceutical.

[0043] The present invention also provides a skin care product, which contains the silicon ether-containing diphenylethylene compound shown in formula I or its pharmaceutically acceptable ester, or its pharmaceutically acceptable alkyl ether as the main effective active ingredient, and one or more excipients acceptable to skin care products can also be added to improve the absorption effect of cosmeceuticals or facilitate use, such as making lotions, oil makeup, emulsions, creams, solids and sprays, etc.; the excipients described in the present invention include conventional moisturizers, emulsifiers, mink oil, grease, polysiloxane, powder raw materials, flavors, pigments, waxes, fatty acids, fatty alcohols, etc. in the field of cosmetics.

[0044] Compared with the prior art, the beneficial technical effects of the present invention are:

[0045] The compound of the present invention belongs to a collagenase inhibitor and can be used for skin aging caused by photoaging. Compared with resveratrol and oxidized resveratrol, the compound of the present invention replaces the alcohol structure with a silyl ether structure with better stability, has a more stable structure and a more suitable smell, is more suitable for use as an active ingredient in anti-skin aging skin care products, and has a better cosmeceutical skin care effect. DETAILED DESCRIPTION

[0046] The present invention can be further understood through the preparation implementation examples and pharmacological experiments of the present invention given below, but they do not constitute a limitation on the scope of protection of the present invention. In the present embodiment, conventional methods are used unless otherwise specified, and the reagents used are conventional reagents or reagents prepared according to conventional methods unless otherwise specified.

[0047] Example 1: Preparation of (E)-4-(3,5-dimethoxyphenylvinyl)-3-triethylsilylphenol

[0048]

[0049] The specific contents are as follows:

[0050] Step 1: Preparation of (E)-4-(2-(triethylsilyl)vinyl)-1,3-benzenediol:

[0051] Weigh 6-benzofuranol (134.1 mg, 1 mmol) and triethylsilylboronic acid pinacol ester (363.3 mg, 1.5 mmol) into a round-bottom flask, add ethylene glycol dimethyl ether (4 mL), stir to dissolve, then add potassium tert-butoxide (224.4 mg, 2.0 mmol), pass nitrogen, seal and stir for 12 hours. Add dilute hydrochloric acid (2N, 5 mL), extract with dichloromethane, dry the extract with anhydrous magnesium sulfate, filter, concentrate, and purify by column chromatography to obtain 225.4 mg of (E)-4-(2-(triethylsilyl)vinyl)-1,3-benzenediol, with a yield of 90%. 1H NMR(500MHz,Chloroform-d)δ7.22(d,J=8.2Hz,1H),7.13(d,J=16.3Hz,1H),6.39– 6.28(m,2H),6.21(d,J=16.3Hz,1H),0.86(t,J=7.8Hz,9H),0.42(q,J=7.8Hz,6H).

[0052] Step 2: Preparation of (E)-4-(2-iodovinyl)-3-triethylsilylphenol:

[0053] Weigh (E)-4-(2-(triethylsilyl)vinyl)-1,3-benzenediol (250.4 mg, 1 mmol) and N-iodosuccinimide (450.0 mg, 2 mmol), add acetonitrile (4 mL), stir at room temperature for 1 h, add water, extract with dichloromethane to obtain 301.0 mg of (E)-4-(2-iodovinyl)-3-triethylsilyloxyphenol, with a yield of 80%. 1 H NMR(500MHz,Chloroform-d)δ7.69–7.57(m,1H),7.26(dd,J=8.8,0.4Hz,1H),7.19(d,J=13.2Hz,1H ),6.64(dd,J=8.8,2.2Hz,1H),6.41(d,J=2.1Hz,1H),1.08(t,J=8.1Hz,9H),0.71(q,J=8.0Hz,6H).

[0054] Step 3: Preparation of (E)-4-(3,5-dimethoxyphenylvinyl)-3-triethylsilylphenol:

[0055] Weigh (E)-4-(2-iodovinyl)-3-triethylsilylphenol (188.1 mg, 0.5 mmol), 3,5-dimethoxyphenylboronic acid (109.2 mg, 0.6 mmol), Pd(PPh 3 ) 4 (28.8 mg, 0.025 mmol) and K 2 CO 3 (172.8 mg, 1.25 mmol) was added to a round-bottom flask, and toluene (2.5 mL) and water (0.5 mL) were added, stirred, heated to 110°C, and reacted for 12 hours. After the reaction was completed, an appropriate amount of water was added, extracted with dichloromethane, dried over anhydrous magnesium sulfate, and concentrated to obtain a crude product, which was purified by column chromatography to obtain 125.0 mg of (E)-4-(3,5-dimethoxyphenylvinyl)-3-triethylsilyloxyphenol, with a yield of 65%. 1H NMR(500MHz,Chloroform-d)δ7.46–7.29(m,2H),6.98(d,J=16.5Hz,1H),6.70–6.58( m,3H),6.45–6.31(m,2H),3.81(s,6H),1.08(t,J=8.1Hz,9H),0.71(q,J=8.0Hz,6H).

[0056] Example 2: Preparation of (E)-5-(4-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol

[0057]

[0058] Step 1, preparation of (E)-5-(4-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol: weigh (E)-4-(3,5-dimethoxyphenylvinyl)-3-triethylsilyloxyphenol (386.0 mg, 1 mmol) and dissolve it in dichloromethane, cool it to -78 °C, and add BBr dropwise. 3 (0.33mL, 3.3mmol), slowly heated to room temperature, reacted for 12h. After the reaction was completed, added appropriate amount of water, extracted with dichloromethane, dried over anhydrous magnesium sulfate, purified by column chromatography, and obtained (E)-5-(4-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol 322mg, yield 90%. 1 H NMR(500MHz,Chloroform-d)δ7.45–7.28(m,2H),6.91(d,J=16.3Hz,1H),6.64(dd,J=8.8,2.2Hz,1H),6.43( d,J=2.0Hz,2H),6.34(d,J=2.2Hz,1H),6.15(t,J=1.9Hz,1H),1.08(t,J=8.1Hz,9H),0.71(q,J=8.0Hz,6H).

[0059] Example 3: Preparation of (E)-4-(3,5-dimethoxyphenylvinyl)-4-triethylsilylphenol

[0060]

[0061] The synthesis method is the same as in Example 1, except that:

[0062] Step 1, preparation of (E)-4-(2-(triethylsilyl)vinyl)-1,4-benzenediol: 5-benzofuranol was used as a raw material and the method of step 1 in Example 1 was used to prepare (E)-4-(2-(triethylsilyl)vinyl)-1,4-benzenediol by ring-opening silylation reaction. 1H NMR(500MHz,Chloroform-d)δ6.95(d,J=16.3Hz,1H),6.84–6.73(m,2H),6.48(dd,J= 8.6, 2.2Hz, 1H), 6.26 (d, J = 16.3Hz, 1H), 0.86 (t, J = 7.8Hz, 9H), 0.42 (q, J = 7.8Hz, 6H).

[0063] Step 2, preparation of (E)-3-(2-iodovinyl)-4-triethylsiloxyphenol: (E)-3-(2-iodovinyl)-4-triethylsiloxyphenol was obtained by the method of step 2 of example 1. 1 H NMR(500MHz,Chloroform-d)δ7.45(d,J=13.3Hz,1H),7.20(d,J=13.4Hz,1H),6. 95–6.86(m,1H),6.78–6.67(m,2H),1.08(t,J=8.0Hz,9H),0.72(q,J=8.0Hz,6H).

[0064] Step 3, preparation of (E)-4-(3,5-dimethoxyphenylvinyl)-4-triethylsiloxyphenol: (E)-4-(3,5-dimethoxyphenylvinyl)-4-triethylsiloxyphenol was obtained by the method of step 3 of example 1. 1 H NMR(500MHz,Chloroform-d)δ7.29(d,J=16.3Hz,1H),6.97(d,J=16.3Hz,1H),6.86(d,J=8.7Hz,1H),6.75(d,J=2.2Hz,1H),6.69 (dd,J=8.7,2.3Hz,1H),6.64(d,J=2.1Hz,2H),6.41(t,J=2.2Hz,1H),3.81(s,6H),1.08(t,J=8.0Hz,9H),0.72(q,J=8.0Hz,6H).

[0065] Example 4: Preparation of (E)-5-(5-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol

[0066]

[0067] The synthesis method is the same as that in Example 2, and (E)-5-(5-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol is obtained by demethylation. 1H NMR(500MHz,Chloroform-d)δ7.29(d,J=16.3Hz,1H),6.97–6.83(m,2H),6.79–6.63(m,2H) ,6.43(d,J=2.0Hz,2H),6.15(t,J=1.9Hz,1H),1.08(t,J=8.0Hz,9H),0.72(q,J=8.0Hz,6H).

[0068] Example 5: Preparation of (E)-(2-(3,5-dimethoxyphenylvinyl)-5-methoxyphenoxy)triethylsilane.

[0069]

[0070] Step 1: Preparation of (E)-5-methoxy-2-(2-triethylsilylvinyl)phenol: (E)-5-methoxy-2-(2-triethylsilylvinyl)phenol was prepared by ring-opening silylation using the method of step 1 of example 1. 1 H NMR(500MHz,Chloroform-d)δ7.36(dd,J=8.4,0.4Hz,1H),7.21–7.03(m,1H),6.63(dd,J=8.3,2.3Hz,1H) ,6.48(d,J=2.2Hz,1H),6.21(d,J=16.3Hz,1H),3.82(s,3H),0.86(t,J=7.8Hz,9H),0.42(q,J=7.8Hz,6H).

[0071] Step 2: Preparation of (E)-triethyl (2-(2-iodovinyl)-5-methoxyphenoxy) silane: iodine to obtain (E)-triethyl (2-(2-iodovinyl)-5-methoxyphenoxy) silane by the method of step 2 of example 1. 1 H NMR(500MHz,Chloroform-d)δ7.73–7.56(m,1H),7.45(dd,J=9.0,0.4Hz,1H),7.19(d,J=13.2Hz,1H),6.7 2(dd,J=9.0,2.4Hz,1H),6.51(d,J=2.4Hz,1H),3.82(s,3H),1.08(t,J=8.1Hz,9H),0.71(q,J=8.0Hz,6H).

[0072] Step 3: Preparation of (E)-(2-(3,5-dimethoxyphenylvinyl)-5-methoxyphenoxy)triethylsilane: The method of step 3 of example 1 is used to obtain (E)-(2-(3,5-dimethoxyphenylvinyl)-5-methoxyphenoxy)triethylsilane through coupling reaction. 1H NMR(500MHz,Chloroform-d)δ7.60–7.47(m,1H),7.44–7.33(m,1H),6.98(d,J=16.5Hz,1H),6.72(dd,J=9.0,2.4Hz ,1H),6.64(d,J=2.1Hz,2H),6.55–6.35(m,2H),3.81(d,J=4.6Hz,9H),1.08(t,J=8.1Hz,9H),0.71(q,J=8.0Hz,6H).

[0073] Example 6: Preparation of (E)-4-(3,5-dihydroxyphenylvinyl)-3-(triethylsilyl)phenyl acetate

[0074]

[0075] The synthesis method is the same as in Example 2, except that step 1:

[0076] Step 1: Preparation of (E)-3-hydroxy-4-(2-(triethylsilyl)vinyl)phenyl acetate: The method of step 1 in Example 1 was used, except that 6-benzofuran acetate was used as a raw material to obtain (E)-3-hydroxy-4-(2-(triethylsilyl)vinyl)phenyl acetate. 1 H NMR(500MHz,Chloroform-d)δ7.36(dd,J=8.3,0.5Hz,1H),7.20–7.08(m,1H),6.96(dd,J=8.4,2.2Hz,1H) ,6.78(d,J=2.3Hz,1H),6.21(d,J=16.3Hz,1H),2.30(s,3H),0.86(t,J=7.8Hz,9H),0.42(q,J=7.8Hz,6H).

[0077] After obtaining (E)-3-hydroxy-4-(2-(triethylsilyl)vinyl)phenyl acetate, (E)-4-(3,5-dihydroxyphenylvinyl)-3-(triethylsilyl)phenyl acetate was prepared by the same method as in Example 2. 1 H NMR(500MHz,Chloroform-d)δ7.50(dd,J=8.6,0.4Hz,1H),7.42–7.26(m,1H),7.03–6.84(m,2H),6.70(d,J=2.4 Hz, 1H), 6.43 (d, J = 2.0Hz, 2H), 6.15 (t, J = 1.9Hz, 1H), 2.30 (s, 3H), 1.08 (t, J = 8.1Hz, 9H), 0.71 (q, J = 8.0Hz, 6H).

[0078] Example 7: Preparation of (E)-5-(4-acetoxy-2-(triethylsilyloxy)phenylvinyl-1,3-benzenediol acetate

[0079]

[0080] The synthesis method is the same as in Examples 2 and 6, except that:

[0081] Step 1: Use the synthesis method of Examples 2 and 6 to obtain (E)-4-(3,5-dihydroxyphenylvinyl)-3-(triethylsilyl)phenyl acetate, weigh the above compound (400 mg, 1 mmol), add it to a round-bottom flask, add 5 mL of 1% TfOH / MeCN solution, slowly add acetyl chloride (0.2 mL, 3 mmol), and react at room temperature for 2 hours. Add water, extract with dichloromethane, concentrate, and purify by column chromatography to obtain 1.34 g of (E)-5-(4-acetoxy-2-(triethylsilyl)phenylvinyl-1,3-benzenediol acetate, with a yield of 92%. 1 H NMR(500MHz,Chloroform-d)δ7.50(dd,J=8.6,0.4Hz,1H),7.36(dd,J=16.5,0.6Hz,1H),7.21(d,J=1.8Hz,2H),7.06– 6.91(m,2H),6.83(t,J=1.9Hz,1H),6.70(d,J=2.4Hz,1H),2.30(s,9H),1.08(t,J=8.1Hz,9H),0.71(q,J=8.0Hz,6H).

[0082] Example 8: Preparation of (E)-4-(3,5-difluorophenylvinyl)-3-(triethylsilyl)phenyl acetate

[0083]

[0084] The synthesis method is the same as that of Example 6, except that 3,5-difluorophenylboronic acid is used as the raw material for the coupling reaction to obtain (E)-4-(3,5-difluorophenylvinyl)-3-(triethylsilyl)phenyl acetate. 1 H NMR(500MHz,Chloroform-d)δ7.50(dd,J=8.6,0.4Hz,1H),7.42–7.31(m,1H),7.14–7.05(m,2H),7.05–6.93(m,2 H), 6.88 (tt, J = 8.1, 2.1Hz, 1H), 6.70 (d, J = 2.4Hz, 1H), 2.30 (s, 3H), 1.08 (t, J = 8.1Hz, 9H), 0.71 (q, J = 8.0Hz, 6H).

[0085] Example 9: Test for inhibition of collagenase (MMP-1) activity

[0086] In vitro MMP-1 activity assay

[0087] The inhibitory effects of compounds 1, 2, 6, and 7 on MMP-1 enzyme activity in a cell-free system were evaluated using the MMP-1 fluorescent drug discovery kit (Enzo Life Sciences, Inc.). The assay kit included a specific MMP-1 inhibitor (NNGH) as a control inhibitor. The reaction mixture was incubated at 37°C for 5 minutes. ex / λ em MMP-1 activity was measured by fluorescence signal at 540 / 590 nm and calculated as a percentage relative to the enzyme-treated control.

[0088] Table 1. Experimental results of inhibition of collagenase (MMP-1) activity by some compounds of the present invention

[0089]

[0090] The above is only a preferred embodiment of the present invention. It should be noted that, for those skilled in the art, several improvements and supplements may be made without departing from the method of the present invention, and these possible improvements and supplements should also be considered as the protection scope of the present invention.

Claims

1. A type of silylene compound containing silylene, characterized in that: The compound is: (E)-4-(3,5-dimethoxyphenylvinyl)-3-triethylsilylphenol; (E)-5-(4-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol; (E)-4-(3,5-dimethoxyphenylvinyl)-4-triethylsilylphenol; (E)-5-(5-hydroxy-2-(triethylsilyloxy)phenylvinyl)-1,3-benzenediol; (E)-(2-(3,5-dimethoxyphenylvinyl)-5-methoxyphenoxy)triethylsilyl; (E)-4-(3,5-dihydroxyphenylvinyl)-3-(triethylsilyloxy)phenyl acetate; (E)-5-(4-acetoxy-2-(triethylsilyloxy)phenylvinyl-1,3-benzenediol acetate; or (E)-4-(3,5-Difluorophenylvinyl)-3-(triethylsilyloxy)phenyl acetate.

2. The method for preparing the compound according to claim 1, characterized in that: include: The ring-opening silylation of benzofuran is mediated by a base to realize the ring-opening silylation of styrene silane, which is iodinated with N-iodosuccinimide to transfer the silicon group, and then the compound is obtained through a coupling reaction.

3. Use of the compound according to claim 1 in the preparation of cosmetics.

4. The use according to claim 3, characterized in that: The cosmetics are anti-skin aging cosmeceuticals.

5. A skin care product, characterized in that: The invention comprises the compound as claimed in claim 1 and necessary auxiliary materials.

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