CN106188128A - A kind of Tricyclohexyltin 2 naphthoate coordination compound and preparation method and application - Google Patents

A kind of Tricyclohexyltin 2 naphthoate coordination compound and preparation method and application Download PDF

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CN106188128A
CN106188128A CN201610567951.6A CN201610567951A CN106188128A CN 106188128 A CN106188128 A CN 106188128A CN 201610567951 A CN201610567951 A CN 201610567951A CN 106188128 A CN106188128 A CN 106188128A
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tricyclohexyltin
naphthoate
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CN106188128B (en
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朱小明
蒋伍玖
邝代治
张复兴
冯泳兰
庾江喜
谭宇星
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Hengyang Normal University
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Abstract

A kind of Tricyclohexyltin 2 naphthoate coordination compound disclosed by the invention and preparation method and application, for the coordination compound of following structure formula (I).The invention also discloses the preparation method of Tricyclohexyltin 2 naphthoate coordination compound and the application in preparing antitumor drug.

Description

A kind of Tricyclohexyltin 2-naphthoate coordination compound and preparation method and application
Technical field
The present invention relates to a kind of Tricyclohexyltin 2-naphthoate coordination compound, and preparation method thereof, and this coordination compound three The application in preparing antitumor drug of the cyclohexyl stannum 2-naphthoate.
Background technology
Organotin is the metallo-organic compound that a class contains Sn-C key, has higher biological activity, in sterilization, kills Worm, cancer therapy drug the field such as are prepared and are had a wide range of applications.Existing research shows, the alkyl R in organotin is to determine The principal element of compound anti-cancering activity height, e.g., the active anticancer of cyclohexyl, normal-butyl and phenyltin compound is relatively strong, second Base takes second place, and methyl is then almost without active anticancer.The structure of part is to the active anticancer of coordination compound and the wide spectrum of killing cancerous cell Property also plays an important role, it is demonstrated experimentally that the biological activity of organotin carboxylate coordination compound is often than corresponding organotin Compound is high.
Double [three (2-methyl-2-phenyl propyl) stannum] monocarboxylate ratios double [three disclosed in European patent EP 0177785B1 (2-methyl-2-phenyl propyl) stannum] oxide has higher biological live.
Chinese patent CN 103396437B discloses double (Tricyclohexyltin) carboxylate at preparation treatment cervical cancer, mammary gland The medicine of cancer, hepatocarcinoma, colon cancer and pulmonary carcinoma is applied.
Being to the experiment proved that to have preferable bioactive material based on tin tricyclohexylhydroxide, the present invention selects three rings Hexyl stannic hydroxide, with part 2-naphthoic acid, reacts under certain condition, and synthesis has obtained NCI-H460(people's pulmonary carcinoma thin Born of the same parents), MCF7(people's breast adenocarcinoma cell), HEPG2(human liver cancer cell) the stronger compound of inhibitory activity, for exploitation anticarcinogen Thing provides new way.
Summary of the invention
The problem existed for above-mentioned prior art, the first object of the present invention there is provided a kind of Tricyclohexyltin 2-naphthalene Formic acid esters coordination compound.
The second object of the present invention is to provide the preparation method of above-mentioned Tricyclohexyltin 2-naphthoate coordination compound.
3rd mesh of the present invention is to provide above-mentioned Tricyclohexyltin 2-naphthoate coordination compound in preparing cancer therapy drug Application.
As a kind of Tricyclohexyltin 2-naphthoate coordination compound of first aspect present invention, it is following structure formula (I) Coordination compound:
(I)。
The Tricyclohexyltin 2-naphthoate coordination compound of the present invention is through elementary analysis, infrared spectrum analysis, nuclear magnetic resoance spectrum And x-ray crystal structure analysis, result is as follows:
Elementary analysis (C30H44O3Sn): theoretical value: C, 63.06；H, 7.76.Measured value: C, 62.91；H, 7.81.
IR(KBr, v/cm-1): 3057, 2918, 2845 v(C-H), 1639 vas(COO-), 1329 vs (COO-), 605 v(Sn-C), 416 v(Sn-O)。
1H NMR(CDCl3, 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H, CH3-), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH)。
13C NMR(CDCl3, 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C), 50.91(MeOH), 126.23, 126.47, 127.60, 127.68, 127.75, 129.28, 129.62, 131.19, 132.65, 135.15(Ar-C), 171.46(-COO)。
119Sn NMR(CDCl3, 186 MHz), δ (ppm): 16.09。
The Tricyclohexyltin 2-naphthoate coordination compound of the present invention is crystal structure, its crystallographic data: crystal belongs to monocline Crystallographic system, space groupP21/n,a=1.12488 (8) nm,b=1.99595 (15) nm,c=1.35539 (10) nm,α=90 °,β= 107.9560 (10) °,γ=90 °,Z=4, V=2.8949 (4) nm3,Dc=1.311Mg·m-3,μ(MoKa)=0.763mm-1,F (000)=1192,1.88 ° of ＜θ＜ 27.45 °, crystalline size: 0.32 x 0.23 x 0.16mm,R=0.0269,wR= 0.0582。
Being structurally characterized in that of the Tricyclohexyltin 2-naphthoate coordination compound of the present invention: center tin atom and three carbon atoms With two oxygen atom ligands, define pentacoordinate distortion trigonal biyramid configuration.
As the preparation method of a kind of Tricyclohexyltin 2-naphthoate coordination compound of second aspect present invention, hold in reaction Device is sequentially added into naphthoic acid, tin tricyclohexylhydroxide and solvent absolute methanol in order, in the condition that temperature is 50 ~ 65 DEG C Lower reaction response 8～20h；Cooling, filters, and controls solvent volatilization crystallization, obtain colourless transparent crystal under conditions of 20 ~ 35 DEG C, It is Tricyclohexyltin 2-naphthoate coordination compound.
In a preferred embodiment of the invention, the amount of the material of described naphthoic acid, both tin tricyclohexylhydroxides Ratio is 1:(1 ~ 1.05).
In a preferred embodiment of the invention, described solvent absolute methanol consumption is every mM of thricyclohexyl hydrogen-oxygen Change stannum add 15 ~ 35 milliliters.
As a kind of Tricyclohexyltin 2-naphthoate coordination compound of third aspect present invention in preparing cancer therapy drug Application.
Applicant has carried out anti tumor activity in vitro and has confirmed research above-mentioned coordination compound, confirms that this is joined and has certain with thing Anti-tumor biological, say, that the purposes of above-mentioned coordination compound is the application in preparing antitumor drug, the most just It it is the application in preparing anti-human lung-cancer medicament, human breast carcinoma, people's liver-cancer medicine.
The Tricyclohexyltin 2-naphthoate coordination compound of the present invention is to people's lung-cancer medicament, human breast carcinoma, people's liver-cancer medicine etc. Demonstrate good active anticancer, anti-lung cancer, anti-breast cancer, medicines resistant to liver cancer can be prepared with it for raw material.With generally make at present Platinum-containing anticancer drug compare, the Tricyclohexyltin 2-naphthoate coordination compound of the present invention have active anticancer height, low cost, The features such as preparation method is simple, provide new way for exploitation cancer therapy drug.
Accompanying drawing explanation
Fig. 1 is the crystal molecular structure figure of Tricyclohexyltin 2-naphthoate coordination compound.
Fig. 2 is the IR spectrogram of Tricyclohexyltin 2-naphthoate coordination compound.
Fig. 3 is Tricyclohexyltin 2-naphthoate coordination compound1H NMR spectra.
Fig. 4 is Tricyclohexyltin 2-naphthoate coordination compound13C NMR spectra.
Fig. 5 is Tricyclohexyltin 2-naphthoate coordination compound119Sn NMR spectra.
Detailed description of the invention
Further describe the present invention by following example, but it should be noted that the scope of the present invention is not implemented by these Any restriction of example.
Embodiment 1:
The preparation of Tricyclohexyltin 2-naphthoate coordination compound:
Naphthoic acid 0.172g (1mmol), tin tricyclohexylhydroxide 0.385g it is sequentially added in order in 100ml round-bottomed flask (1mmol), solvent absolute methanol 20mL, reaction 8h under conditions of temperature is 50 ~ 65 DEG C；Cooling, filters, at 20 ~ 35 DEG C Under the conditions of control solvent volatilization crystallization, obtain colourless transparent crystal, be Tricyclohexyltin 2-naphthoate.Productivity: 68%, fusing point: 205~206℃。
Elementary analysis (C30H44O3Sn): theoretical value: C, 63.06；H, 7.76.Measured value: C, 62.91；H, 7.81.
IR(KBr, v/cm-1): 3057, 2918, 2845 v(C-H), 1639 vas(COO-), 1329 vs (COO-), 605 v(Sn-C), 416 v(Sn-O)。
1H NMR(CDCl3, 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H, CH3-), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH)。
13C NMR(CDCl3, 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C), 50.91(MeOH), 126.23, 126.47, 127.60, 127.68, 127.75, 129.28, 129.62, 131.19, 132.65, 135.15(Ar-C), 171.46(-COO)。
119Sn NMR(CDCl3, 186 MHz), δ (ppm): 16.09。
Crystallographic data: crystal belongs to monoclinic system, space groupP21/n,a=1.12488 (8) nm,b=1.99595 (15) nm,c=1.35539 (10) nm,α=90 °,β=107.9560 (10) °,γ=90 °,Z=4, V=2.8949 (4) nm3,Dc= 1.311Mg·m-3,μ(MoKa)=0.763mm-1,F(000)=1192,1.88 ° of ＜θ＜ 27.45 °, crystalline size: 0.32 x 0.23 x 0.16mm,R=0.0269,wR=0.0582。
Embodiment 2:
The preparation of Tricyclohexyltin 2-naphthoate coordination compound:
Naphthoic acid 0.172g (1mmol), tin tricyclohexylhydroxide 0.404g it is sequentially added in order in 100ml round-bottomed flask (1.05mmol), solvent absolute methanol 37mL, reaction 13h under conditions of temperature is 50 ~ 65 DEG C；Cooling, filters, 20 ~ 35 Control solvent volatilization crystallization under conditions of DEG C, obtain colourless transparent crystal, be Tricyclohexyltin 2-naphthoate.Productivity: 69%, Fusing point: 205 ~ 206 DEG C.
Elementary analysis (C30H44O3Sn): theoretical value: C, 63.06；H, 7.76.Measured value: C, 62.91；H, 7.81.
IR(KBr, v/cm-1): 3057, 2918, 2845 v(C-H), 1639 vas(COO-), 1329 vs (COO-), 605 v(Sn-C), 416 v(Sn-O)。
1H NMR(CDCl3, 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H, CH3-), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH)。
13C NMR(CDCl3, 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C), 50.91(MeOH), 126.23, 126.47, 127.60, 127.68, 127.75, 129.28, 129.62, 131.19, 132.65, 135.15(Ar-C), 171.46(-COO)。
119Sn NMR(CDCl3, 186 MHz), δ (ppm): 16.09。
Crystallographic data: crystal belongs to monoclinic system, space groupP21/n,a=1.12488 (8) nm,b=1.99595 (15) nm,c=1.35539 (10) nm,α=90 °,β=107.9560 (10) °,γ=90 °,Z=4, V=2.8949 (4) nm3,Dc= 1.311Mg·m-3,μ(MoKa)=0.763mm-1,F(000)=1192,1.88 ° of ＜θ＜ 27.45 °, crystalline size: 0.32 x 0.23 x 0.16mm,R=0.0269,wR=0.0582。
Embodiment 3:
The preparation of Tricyclohexyltin 2-naphthoate coordination compound:
Naphthoic acid 0.518g (3mmol), tin tricyclohexylhydroxide 1.212g it is sequentially added in order in 100ml round-bottomed flask (3.15mmol), solvent absolute methanol 63mL, reaction 20h under conditions of temperature is 50 ~ 65 DEG C；Cooling, filters, 20 ~ 35 Control solvent volatilization crystallization under conditions of DEG C, obtain colourless transparent crystal, be Tricyclohexyltin 2-naphthoate.Productivity: 65%, Fusing point: 205 ~ 206 DEG C.
Elementary analysis (C30H44O3Sn): theoretical value: C, 63.06；H, 7.76.Measured value: C, 62.91；H, 7.81.
IR(KBr, v/cm-1): 3057, 2918, 2845 v(C-H), 1639 vas(COO-), 1329 vs (COO-), 605 v(Sn-C), 416 v(Sn-O)。
1H NMR(CDCl3, 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H, CH3-), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH)。
13C NMR(CDCl3, 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C), 50.91(MeOH), 126.23, 126.47, 127.60, 127.68, 127.75, 129.28, 129.62, 131.19, 132.65, 135.15(Ar-C), 171.46(-COO)。
119Sn NMR(CDCl3, 186 MHz), δ (ppm): 16.09。
Crystallographic data: crystal belongs to monoclinic system, space groupP21/n,a=1.12488 (8) nm,b=1.99595 (15) nm,c=1.35539 (10) nm,α=90 °,β=107.9560 (10) °,γ=90 °,Z=4, V=2.8949 (4) nm3,Dc= 1.311Mg·m-3,μ(MoKa)=0.763mm-1,F(000)=1192,1.88 ° of ＜θ＜ 27.45 °, crystalline size: 0.32 x 0.23 x 0.16mm,R=0.0269,wR=0.0582。
Embodiment 4:
The preparation of Tricyclohexyltin 2-naphthoate coordination compound:
Naphthoic acid 0.517g (3mmol), tin tricyclohexylhydroxide 1.16g it is sequentially added in order in 100ml round-bottomed flask (3mmol), solvent absolute methanol 60mL, reaction 20h under conditions of temperature is 50 ~ 65 DEG C；Cooling, filters, at 20 ~ 35 DEG C Under the conditions of control solvent volatilization crystallization, obtain colourless transparent crystal, be Tricyclohexyltin 2-naphthoate.Productivity: 66%, fusing point: 205~206℃。
Elementary analysis (C30H44O3Sn): theoretical value: C, 63.06；H, 7.76.Measured value: C, 62.91；H, 7.81.
IR(KBr, v/cm-1): 3057, 2918, 2845 v(C-H), 1639 vas(COO-), 1329 vs (COO-), 605 v(Sn-C), 416 v(Sn-O)。
1H NMR(CDCl3, 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H, CH3-), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH)。
13C NMR(CDCl3, 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C), 50.91(MeOH), 126.23, 126.47, 127.60, 127.68, 127.75, 129.28, 129.62, 131.19, 132.65, 135.15(Ar-C), 171.46(-COO)。
119Sn NMR(CDCl3, 186 MHz), δ (ppm): 16.09。
Crystallographic data: crystal belongs to monoclinic system, space groupP21/n,a=1.12488 (8) nm,b=1.99595 (15) nm,c=1.35539 (10) nm,α=90 °,β=107.9560 (10) °,γ=90 °,Z=4, V=2.8949 (4) nm3,Dc= 1.311Mg·m-3,μ(MoKa)=0.763mm-1,F(000)=1192,1.88 ° of ＜θ＜ 27.45 °, crystalline size: 0.32 x 0.23 x 0.16mm,R=0.0269,wR=0.0582。
Embodiment 5:
The preparation of Tricyclohexyltin 2-naphthoate coordination compound:
Naphthoic acid 0.344g (2mmol), tin tricyclohexylhydroxide 0.809g it is sequentially added in order in 100ml round-bottomed flask (2.10mmol), solvent absolute methanol 60mL, reacts 20h under conditions of temperature is 50 ~ 65 DEG C；Cooling, filters, 20 ~ 35 Control solvent volatilization crystallization under conditions of DEG C, obtain colourless transparent crystal, be Tricyclohexyltin 2-naphthoate.Productivity: 70%, Fusing point: 205 ~ 206 DEG C.
Elementary analysis (C30H44O3Sn): theoretical value: C, 63.06；H, 7.76.Measured value: C, 62.91；H, 7.81.
IR(KBr, v/cm-1): 3057, 2918, 2845 v(C-H), 1639 vas(COO-), 1329 vs (COO-), 605 v(Sn-C), 416 v(Sn-O)。
1H NMR(CDCl3, 500 MHz), δ(ppm): δ 7.51-8.63(m, 7H, Ar-H), 3.49(s, 3H, CH3-), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH)。
13C NMR(CDCl3, 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C), 50.91(MeOH), 126.23, 126.47, 127.60, 127.68, 127.75, 129.28, 129.62, 131.19, 132.65, 135.15(Ar-C), 171.46(-COO)。
119Sn NMR(CDCl3, 186 MHz), δ (ppm): 16.09。
Crystallographic data: crystal belongs to monoclinic system, space groupP21/n,a=1.12488 (8) nm,b=1.99595 (15) nm,c=1.35539 (10) nm,α=90 °,β=107.9560 (10) °,γ=90 °,Z=4, V=2.8949 (4) nm3,Dc= 1.311Mg·m-3,μ(MoKa)=0.763mm-1,F(000)=1192,1.88 ° of ＜θ＜ 27.45 °, crystalline size: 0.32 x 0.23 x 0.16mm,R=0.0269,wR=0.0582。
Test example:
The Tricyclohexyltin 2-naphthoate coordination compound of the present invention, it is real by MTT experiment method that its Anticancer Activity in vitro measures Existing.
MTT analyses method:
With metabolism reduction 3-(4,5-Dimethylthiazol-2-yl)-2,5-diArenyltetrazolium bromide it is Basis.Succinate dehydrogenase in living cells mitochondrion can make exogenous MTT be reduced to water-insoluble bluish violet crystallization first a ceremonial jade-ladle, used in libation (Formazan) and be deposited in cell, and dead cell is without this function.Dimethyl sulfoxide (DMSO) can dissolve the first a ceremonial jade-ladle, used in libation in cell, Measure the optical density of characteristic wavelength by microplate reader, can indirectly reflect living cells quantity.
Mtt assay is used to measure the Tricyclohexyltin 2-naphthoate coordination compound of embodiment 1 preparation to human lung carcinoma cell (NCI-H460), human breast cancer cell (MCF7), the inhibitory activity of human liver cancer cell (HepG2).
Cell strain and cultivating system: NCI-H460, MCF7 and HepG2 cell strain takes from American. tissue incubator (ATCC). By RPMI1640 (GIBICO company) culture medium containing 10% hyclone, at 5% (volume fraction) CO2, 37 DEG C of saturated humidity trainings In vitro culture is carried out in supporting case.
Test process: test medicinal liquid (0.1nM-10uM) is added separately in each hole according to the Concentraton gradient of concentration, Each concentration sets 3 parallel holes.Experiment is divided into drug test group (being separately added into the test medicine of variable concentrations), matched group (only to add Culture fluid and cell, be not added with testing medicine) and blank group (only adding culture fluid, be not added with cell and test medicine).By the orifice plate after dosing It is placed in 37 DEG C, 5%CO2Incubator is cultivated 72h.The activity of control drug measures according to the method for test sample.Cultivating In orifice plate after 72h, every hole adds MTT40uL (being made into 4mg/mL with D-Hanks buffer).After placing 4h at 37 DEG C, remove Clear liquid.Every hole adds 150uL DMSO, and vibrate 5min, makes Formazan crystallization dissolve.Finally, utilize automatic microplate reader at 570nm The optical density in each hole is detected at wavelength.
Data process: data process and use GraAr Pad Prism version5.0 program, compound IC50Pass through program In there is the nonlinear regression model (NLRM) of S-shaped dose response be fitted obtaining.
With MTT analytic process to human lung carcinoma cell (NCI-H460) cell strain, human breast cancer cell (MCF7) cell strain, people liver Cancerous cell (HepG2) cell strain is analyzed, and measures its IC50Value, result is as shown in table 1, and conclusion is: from data in table, The Tricyclohexyltin 2-naphthoate coordination compound of the present invention is as cancer therapy drug, to people's pulmonary carcinoma, human breast carcinoma, the anticancer work of people's hepatocarcinoma Property is higher, can be as the candidate compound of cancer therapy drug.
Table 1 Tricyclohexyltin 2-naphthoate coordination compound coordination compound cancer therapy drug external activity test data.
Human lung carcinoma cell Human breast cancer cell Human liver cancer cell
Cell strain NCI-H460 MC-7 HEPG2
IC50 μM 0.30 0.34 0.35
Tricyclohexyltin 2-naphthoate coordination compound coordination compound prepared by remaining embodiment with mtt assay to human lung carcinoma cell (NCI-H460), human liver cancer cell (HepG2) and the same test example of active anticancer method of testing of human breast cancer cell (MCF7), survey Test result is essentially identical with table 1.

Claims (8)

1. a Tricyclohexyltin 2-naphthoate coordination compound, for the coordination compound of following structure formula (I):
(I)。
2. as claimed in claim 1 containing a kind of Tricyclohexyltin 2-naphthoate coordination compound, its ir data: FT- IR (KBr, v/cm-1): 3057, 2918, 2845 v(C-H), 1639 vas(COO-), 1329 vs(COO-), 605 v (Sn-C), 416 v(Sn-O)；Its nuclear-magnetism modal data:1H NMR(CDCl3, 500 MHz), δ(ppm): δ 7.51-8.63 (m, 7H, Ar-H), 3.49(s, 3H, CH3-), 1.37-2.02(m, 33H, Cy-H), 1.04(s, 1H, MeOH) ；13C NMR(CDCl3, 125 MHz), δ(ppm): δ 26.94, 28.96, 31.17, 33.94(Cy-C), 50.91 (MeOH), 126.23, 126.47, 127.60, 127.68, 127.75, 129.28, 129.62, 131.19, 132.65, 135.15(Ar-C), 171.46(-COO)；119Sn NMR(CDCl3, 186 MHz), δ (ppm): 16.09。
3. Tricyclohexyltin 2-naphthoate coordination compound as claimed in claim 1, wherein, described Tricyclohexyltin 2-naphthalene first Acid esters coordination compound is crystal structure, and its crystallographic data is as follows: monoclinic system, space groupP21/n,a=1.12488 (8) nm,b= 1.99595 (15) nm,c=1.35539 (10) nm,α=90 °,β=107.9560 (10) °,γ=90 °,Z=4, V=2.8949 (4) nm3；Center stannum in molecule and coordination atom constitute pentacoordinate distortion trigonal biyramid configuration.
4. the preparation method of the Tricyclohexyltin 2-naphthoate coordination compound described in claim 1, it is characterised in that hold in reaction Device is sequentially added into naphthoic acid, tin tricyclohexylhydroxide and solvent absolute methanol in order, in the condition that temperature is 50 ~ 65 DEG C Lower reaction response 8～20h；Cooling, filters, and controls solvent volatilization crystallization, obtain colourless transparent crystal under conditions of 20 ~ 35 DEG C, It is Tricyclohexyltin 2-naphthoate.
5. the method for preparation as claimed in claim 4, it is characterised in that described naphthoic acid, both tin tricyclohexylhydroxides The amount of material than for 1:(1 ~ 1.05).
6. the method for preparation as claimed in claim 4, it is characterised in that described solvent absolute methanol consumption is every mM three Cyclohexyl stannic hydroxide adds 20 ~ and 35 milliliters.
7. Tricyclohexyltin 2-naphthoate coordination compound application in preparing cancer therapy drug described in claim 1.
8. the application described in claim 7, wherein said cancerous cell is pulmonary carcinoma, breast carcinoma, hepatocarcinoma.
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CN111057098A (en) * 2019-12-26 2020-04-24 衡阳师范学院 Preparation method and application of tri (2-methyl-2 phenylpropyl) tin 1-naphthoate complex
CN111138487A (en) * 2019-12-26 2020-05-12 衡阳师范学院 Preparation method and application of tricyclohexyltin 1-naphthoate complex
CN111153928A (en) * 2019-12-26 2020-05-15 衡阳师范学院 Preparation method and application of tri (2-methyl-2-phenylpropyl) tin 2-naphthoate complex

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111057098A (en) * 2019-12-26 2020-04-24 衡阳师范学院 Preparation method and application of tri (2-methyl-2 phenylpropyl) tin 1-naphthoate complex
CN111138487A (en) * 2019-12-26 2020-05-12 衡阳师范学院 Preparation method and application of tricyclohexyltin 1-naphthoate complex
CN111153928A (en) * 2019-12-26 2020-05-15 衡阳师范学院 Preparation method and application of tri (2-methyl-2-phenylpropyl) tin 2-naphthoate complex
CN111138487B (en) * 2019-12-26 2023-10-24 衡阳师范学院 Preparation method and application of tricyclohexyltin 1-naphthoate complex

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