CN111187171B - 一种锡(ii)簇化合物及其制备方法和应用 - Google Patents
一种锡(ii)簇化合物及其制备方法和应用 Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 41
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical compound [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title abstract description 15
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 44
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 38
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 25
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 claims abstract description 21
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 16
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 14
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 14
- 239000000706 filtrate Substances 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- -1 trimethylsilyl phenyl Chemical group 0.000 claims abstract description 8
- 239000013078 crystal Substances 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- OEULOFHGYOFYEC-UHFFFAOYSA-N 2-(dimethylamino)benzonitrile Chemical compound CN(C)C1=CC=CC=C1C#N OEULOFHGYOFYEC-UHFFFAOYSA-N 0.000 claims abstract description 4
- JZSSNAVPFLMHDJ-UHFFFAOYSA-N lithium phenyl(trimethylsilyl)azanide Chemical compound [Li+].C[Si](C)(C)[N-]c1ccccc1 JZSSNAVPFLMHDJ-UHFFFAOYSA-N 0.000 claims abstract description 4
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000725 suspension Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 14
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000000047 product Substances 0.000 description 16
- 238000007259 addition reaction Methods 0.000 description 11
- 238000001035 drying Methods 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001718 carbodiimides Chemical class 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 230000001376 precipitating effect Effects 0.000 description 2
- 238000006845 Michael addition reaction Methods 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- RKTYLMNFRDHKIL-UHFFFAOYSA-N copper;5,10,15,20-tetraphenylporphyrin-22,24-diide Chemical compound [Cu+2].C1=CC(C(=C2C=CC([N-]2)=C(C=2C=CC=CC=2)C=2C=CC(N=2)=C(C=2C=CC=CC=2)C2=CC=C3[N-]2)C=2C=CC=CC=2)=NC1=C3C1=CC=CC=C1 RKTYLMNFRDHKIL-UHFFFAOYSA-N 0.000 description 1
- 238000006006 cyclotrimerization reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 150000002909 rare earth metal compounds Chemical class 0.000 description 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
- B01J31/1805—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing nitrogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/65—Metal complexes of amines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/22—Tin compounds
- C07F7/2284—Compounds with one or more Sn-N linkages
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Abstract
本发明提供一种锡(II)簇化合物及其制备方法和应用。锡(II)簇化合物合成步骤:在氮气保护下将三甲基硅基苯(基)氨基锂用乙醚溶解,在丙酮浴条件下加入二甲氨基腈,反应过夜得到PhNC(NMe2)NSiMe3(Li)的乙醚溶液;然后将PhNC(NMe2)NSiMe3(Li)的乙醚溶液在丙酮浴条件下加入到SnCl2的乙醚悬浮液中,慢慢升至室温,反应过夜;静置,过滤,滤液在真空下浓缩,室温下结晶,析出无色晶体,即得锡(II)簇化合物;三甲基硅基苯(基)氨基锂、二甲氨基腈和SnCl2的摩尔比为1:1:1。本发明化合物可作为催化剂用于催化苯胺和N,N'‑二异丙基碳化二亚胺加成生成胍的反应,有较好的应用前景。
Description
技术领域
本发明涉及簇金属化合物,具体涉及一种由四个锡(II)核构成的锡(II)簇化合物及其制备方法和应用。
背景技术
胍基配体作为三原子四电子氮基共轭配体在有机化学、金属有机化学、药物合成及催化领域发挥着越来越重要的作用。胍基金属化合物可催化烯烃聚合、Michael加成反应、芳基异腈酸酯的环三聚等多种反应。稀土金属化合物可用作催化剂催化伯胺或仲胺和碳化二亚胺的加成反应生成胍,单核Sn(II)化合物也可以催化苯胺和碳化二亚胺的加成反应以高收率得到胍。本发明锡(II)簇化合物结构新颖,能很好地催化苯胺和N,N'-二异丙基碳化二亚胺的加成反应。
发明内容
本发明的目的在于提供一种方法简单、易于合成的锡(II)簇化合物及其制备方法和应用。
本发明提供的一种锡(II)簇化合物,其化学结构式为:
本发明提供的一种锡(II)簇化合物的制备方法,包括如下步骤:
在氮气保护下将三甲基硅基苯(基)氨基锂用乙醚溶解,在丙酮浴条件下加入二甲氨基腈,反应过夜得到PhNC(NMe2)NSiMe3(Li)的乙醚溶液;然后将PhNC(NMe2)NSiMe3(Li)的乙醚溶液在丙酮浴条件下加入到SnCl2的乙醚悬浮液中,慢慢升至室温,反应过夜;静置,过滤,滤液在真空下浓缩,室温下结晶,析出无色晶体,即得锡(II)簇化合物;三甲基硅基苯(基)氨基锂、二甲氨基腈和SnCl2的摩尔比为1:1:1。
本发明合成的锡(II)簇化合物能催化苯胺和N,N'-二异丙基碳化二亚胺加成生成胍的反应,可作为催化剂使用。
与现有技术相比本发明具有如下优点和效果:本发明锡(II)簇化合物采用金属有机及常规化学合成方法得到,化合物结构新颖,重复性好,样品纯度高,合成方法简单。本发明构筑的锡(II)簇化合物能催化苯胺和N,N'-二异丙基碳化二亚胺的反应以高收率得到胍,可用作催化剂。
附图说明
图1锡(II)簇化合物的x-射线衍射结构图(为了图片清晰,省略了氢原子)
具体实施方式
实施例1:
锡(II)簇化合物的制备:在氮气保护下将0.36g(2.10mmol)三甲基硅基苯(基)氨基锂加入到已称重的反应瓶中,加入20ml乙醚,在丙酮浴条件下加入二甲氨基腈(0.17ml,2.10mmol),反应过夜得到PhNC(NMe2)NSiMe3(Li)的乙醚溶液;然后将其在丙酮浴条件下加入到SnCl2(0.398g,2.10mmol)的10ml乙醚的悬浮液中,慢慢升至室温,反应过夜;静置,过滤,滤液在真空下浓缩,室温下结晶,析出无色晶体,得锡(II)簇化合物0.261克,产率45.8%。
熔点:88℃(分解)
元素分析:理论值C,38.62;H,3.96;N,15.01%;实测值C,38.32;H,3.82;N,15.21%。
核磁:1H NMR(CDCl3):δ1.22-1.28(Et2O),2.56(s,12H,N(CH3)2),3.09(s,12H,N(CH3)2),2.83-2.93(Et2O),7.00-7.31(m,20H,Ph).13C NMR(CDCl3):δ15.30(Et2O),40.52,42.52(N(CH3)2),65.88(Et2O),122.18(p-CPh),122.47(m-CPh),129.13(o-CPh),148.01(Cipso-Ph),169.43(NCN)。
锡(II)簇化合物的结构(见图1)测定:选择大小为0.20mm×0.20mm×0.20mm的锡(II)簇化合物的单晶在297K下,用Bruker D8 Venture-X射线衍射仪测定单胞及收集数据。使用钼靶X射线光源,衍射角范围3.071°<θ<25.03°,衍射指标为-19≤h≤15,-19≤k≤19,-17≤l≤17,扫描方式为ω\2θ,共收集1800个衍射点其中1651个为独立衍射点,采用SHELXS-97程序和SHELXL-2014/7程序完成结构解析及精修,该化合物结构采用直接法解出,全部非氢原子坐标及各向异性热参数经最小二乘法修正。
晶体参数:分子式C36H44N12Sn4,分子量1119.59,晶系Tetragonal,空间群I 41/a(No.88),晶胞参数Z=4,Dc=1.834Mg/m3,μ(Mo-Kα)=2.478mm-1,T=297(2)K,R1=0.0261,wR2=0.0668。
部分键长与键角[°]:Sn(1)-N(1)2.235(3),N(1)-C(1)1.378(5),N(2)-C(1)1.315(5),N(3)-C(1)1.366(5),Sn(1')-N(2)2.155(3),Sn(1)-N(2')2.147(3);N(1)-C(1)-N(2)119.4(3),N(1)-C(1)-N(3)118.9(3),N(2)-C(1)-N(3)121.7(3),Sn(1)-N(1)-C(1)118.3(2),N(1)-Sn(1)-N(2')94.20(11),Sn(1')-N(2)-Sn(1')114.73(14)。
实施例2:
步骤1,锡(II)簇化合物的制备同实施例1。
步骤2,苯胺和N,N'-二异丙基碳化二亚胺的加成反应:称量0.011g(0.01mmol)的锡(II)簇化合物放到30mL的充满氮气的Schlenk瓶中,加入N,N'-二异丙基碳化二亚胺0.31mL(2.00mmol)和苯胺0.18mL(2.00mmol)。在20℃反应1.0h,用0.5mL水进行水解,用30mL二氯甲烷萃取三次(3×10mL),无水Na2SO4干燥,过滤。滤液抽干,产品用正己烷结晶纯化,得产物胍,收率40.7%。
实施例3:
步骤1,锡(II)簇化合物的制备同实施例1。
步骤2,苯胺和N,N'-二异丙基碳化二亚胺的加成反应:称量0.011g(0.01mmol)的锡(II)簇化合物放到30mL的充满氮气的Schlenk瓶中,加入N,N'-二异丙基碳化二亚胺0.31mL(2.00mmol)和苯胺0.18mL(2.00mmol)。在20℃反应6.0h,用0.5mL水进行水解,用30mL二氯甲烷萃取三次(3×10mL),无水Na2SO4干燥,过滤。滤液抽干,产品用正己烷结晶纯化,得产物胍,收率91.4%。
实施例4:
步骤1,锡(II)簇化合物的制备同实施例1。
步骤2,苯胺和N,N'-二异丙基碳化二亚胺的加成反应:称量0.011g(0.01mmol)的锡(II)簇化合物放到30mL的充满氮气的Schlenk瓶中,加入N,N'-二异丙基碳化二亚胺0.31mL(2.00mmol)和苯胺0.18mL(2.00mmol)。在60℃反应0.20h,用0.5mL水进行水解,用30mL二氯甲烷萃取三次(3×10mL),无水Na2SO4干燥,过滤。滤液抽干,产品用正己烷结晶纯化,得产物胍,收率91.7%。
实施例5:
步骤1,锡(II)簇化合物的制备同实施例1。
步骤2,苯胺和N,N'-二异丙基碳化二亚胺的加成反应:称量0.011g(0.01mmol)的锡(II)簇化合物放到30mL的充满氮气的Schlenk瓶中,加入N,N'-二异丙基碳化二亚胺0.31mL(2.00mmol)和苯胺0.18mL(2.00mmol)。在60℃反应0.4h,用0.5mL水进行水解,用30mL二氯甲烷萃取三次(3×10mL),无水Na2SO4干燥,过滤。滤液抽干,产品用正己烷结晶纯化,得产物胍,收率98.1%。
实施例6:
步骤1,锡(II)簇化合物的制备同实施例1。
步骤2,苯胺和N,N'-二异丙基碳化二亚胺的加成反应:称量0.011g(0.01mmol)的锡(II)簇化合物放到30mL的充满氮气的Schlenk瓶中,加入N,N'-二异丙基碳化二亚胺0.31mL(2.00mmol)和苯胺0.18mL(2.00mmol)。在60℃反应0.5h,用0.5mL水进行水解,用30mL二氯甲烷萃取三次(3×10mL),无水Na2SO4干燥,过滤。滤液抽干,产品用正己烷结晶纯化,得产物胍,收率98.9%。
实施例7:
步骤1,锡(II)簇化合物的制备同实施例1。
步骤2,苯胺和N,N'-二异丙基碳化二亚胺的加成反应:称量0.011g(0.01mmol)的锡(II)簇化合物放到30mL的充满氮气的Schlenk瓶中,加入N,N'-二异丙基碳化二亚胺0.31mL(2.00mmol)和苯胺0.18mL(2.00mmol)。在80℃反应0.1h,用0.5mL水进行水解,用30mL二氯甲烷萃取三次(3×10mL),无水Na2SO4干燥,过滤。滤液抽干,产品用正己烷结晶纯化,得产物胍,收率90.0%。
实施例8:
步骤1,锡(II)簇化合物的制备同实施例1。
步骤2,苯胺和N,N'-二异丙基碳化二亚胺的加成反应:称量0.011g(0.01mmol)的锡(II)簇化合物放到30mL的充满氮气的Schlenk瓶中,加入N,N'-二异丙基碳化二亚胺0.31mL(2.00mmol)和苯胺0.18mL(2.00mmol)。在80℃反应0.2h,用0.5mL水进行水解,用30mL二氯甲烷萃取三次(3×10mL),无水Na2SO4干燥,过滤。滤液抽干,产品用正己烷结晶纯化,得产物胍,收率98.3%。
实施例9:
步骤1,锡(II)簇化合物的制备同实施例1。
步骤2,苯胺和N,N'-二异丙基碳化二亚胺的加成反应:称量0.011g(0.01mmol)的锡(II)簇化合物放到30mL的充满氮气的Schlenk瓶中,加入N,N'-二异丙基碳化二亚胺0.31mL(2.00mmol)和苯胺0.18mL(2.00mmol)。在80℃反应0.4h,用0.5mL水进行水解,用30mL二氯甲烷萃取三次(3×10mL),无水Na2SO4干燥,过滤。滤液抽干,产品用正己烷结晶纯化,得产物胍,收率98.9%。
Claims (3)
2.如权利要求1所述的一种锡(II)簇化合物的制备方法,其特征在于包括如下步骤:
在氮气保护下将三甲基硅基苯(基)氨基锂用乙醚溶解,在丙酮浴条件下加入二甲氨基腈,反应过夜得到PhNC(NMe2)NSiMe3(Li)的乙醚溶液;然后将PhNC(NMe2)NSiMe3(Li)的乙醚溶液在丙酮浴条件下加入到SnCl2的乙醚悬浮液中,慢慢升至室温,反应过夜;静置,过滤,滤液在真空下浓缩,室温下结晶,析出无色晶体,即得锡(II)簇化合物;三甲基硅基苯(基)氨基锂、二甲氨基腈和SnCl2的摩尔比为1:1:1。
3.如权利要求1所述的锡(II)簇化合物作为催化剂在催化苯胺和N,N'-二异丙基碳化二亚胺加成生成胍中的应用。
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