CN109666039A - 一种五核锡（ii）化合物及其制备方法和应用 - Google Patents
一种五核锡（ii）化合物及其制备方法和应用 Download PDFInfo
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- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- IUTCEZPPWBHGIX-UHFFFAOYSA-N tin(2+) Chemical class [Sn+2] IUTCEZPPWBHGIX-UHFFFAOYSA-N 0.000 title claims abstract description 12
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims abstract description 28
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims abstract description 24
- -1 dimethylamino nitrile Chemical class 0.000 claims abstract description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000006243 chemical reaction Methods 0.000 claims abstract description 19
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 14
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims abstract description 13
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000000706 filtrate Substances 0.000 claims abstract description 10
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- KXFSUVJPEQYUGN-UHFFFAOYSA-N trimethyl(phenyl)silane Chemical compound C[Si](C)(C)C1=CC=CC=C1 KXFSUVJPEQYUGN-UHFFFAOYSA-N 0.000 claims abstract description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000003054 catalyst Substances 0.000 claims abstract description 7
- 229910021626 Tin(II) chloride Inorganic materials 0.000 claims abstract description 5
- 239000013078 crystal Substances 0.000 claims abstract description 4
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000004090 dissolution Methods 0.000 claims abstract description 3
- 229910000071 diazene Inorganic materials 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 claims 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 1
- 239000000758 substrate Substances 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 11
- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 5
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 6
- 238000007259 addition reaction Methods 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 6
- 230000008025 crystallization Effects 0.000 description 6
- 239000002027 dichloromethane extract Substances 0.000 description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 150000001448 anilines Chemical class 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052761 rare earth metal Inorganic materials 0.000 description 2
- 150000002910 rare earth metals Chemical class 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 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
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 150000008301 phosphite esters Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 229910001432 tin ion Inorganic materials 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
-
- 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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4277—C-X Cross-coupling, e.g. nucleophilic aromatic amination, alkoxylation or analogues
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0202—Polynuclearity
- B01J2531/0205—Bi- or polynuclear complexes, i.e. comprising two or more metal coordination centres, without metal-metal bonds, e.g. Cp(Lx)Zr-imidazole-Zr(Lx)Cp
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/02—Compositional aspects of complexes used, e.g. polynuclearity
- B01J2531/0213—Complexes without C-metal linkages
-
- 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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/40—Complexes comprising metals of Group IV (IVA or IVB) as the central metal
- B01J2531/42—Tin
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
本发明提供一种五核锡(II)化合物及其制备方法和应用。化合物合成步骤：在氮气保护下将三甲基硅基苯(基)氨基锂加入到反应容器中,加入乙醚溶解,在丙酮浴条件下加入二甲氨基腈，反应过夜,在丙酮浴条件下再加入SnCl2,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，得五核锡(II)化合物；所述的三甲基硅基苯(基)氨基锂、二甲氨基腈和SnCl2的摩尔比为1:1:1‑1.25。该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
本发明涉及多核金属化合物，具体涉及基于二价锡离子和胍基配体构筑的一种五核锡(II)化合物及其制备方法和应用。
背景技术
具有CN3结构的胍化合物作为一种有机碱能够催化Michael加成反应、Henry反应、亚磷酸酯与不饱和羰基化合物的加成和酯化反应，在制药、有机金属、配位化学以及有机合成等领域发挥着越来越重要的作用。
对称的具有功能基的取代胍在生物及制药工业上有着重要应用，其合成常采用胺和碳化二亚胺的催化加成得到。所使用的催化剂为半三明治夹心型的、桥联脒基、β-二亚胺或其类似的β-酮胺等配体支持的稀土金属催化剂。但催化剂合成所采用的稀土金属成本高，且合成过程较复杂。
发明内容
本发明的目的在于提供一种合成成本较低、方法简单的五核锡(II)化合物及其制备方法和应用。
本发明提供的一种五核锡化合物，是采用三甲基硅基苯(基)氨基锂为原料，和二甲氨基腈加成、与无水二氯化锡反应而得到，其化学结构式为：
本发明提供的一种五核锡(II)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)氨基锂加入到反应容器中,加入乙醚溶解,在丙酮浴条件下加入二甲氨基腈，反应过夜,在丙酮浴条件下再加入SnCl2,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，得五核锡(II)化合物；所述的三甲基硅基苯(基)氨基锂、二甲氨基腈和SnCl2的摩尔比为1:1:1-1.25。
所述的三甲基硅基苯(基)氨基锂、二甲氨基腈和SnCl2的摩尔比优选为1:1:1.25。
本发明合成的五核锡(II)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：本发明五核锡(II)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，样品纯度高，稳定性好，合成成本低、方法简单。该发明构筑的五核锡(II)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。
具体实施方式
实施例1：
五核锡(II)化合物a的制备：在氮气保护下将0.50g(2.92mmol)三甲基硅基苯(基)氨基锂加入到已称重的反应瓶中,加入30ml乙醚,在丙酮浴条件下加入二甲氨基腈(0.24ml,2.92mmol),反应过夜,在丙酮浴条件下再加入SnCl2(0.69g，3.65mmol),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，得五核锡(II)化合物a 0.256克,产率24.4％。
熔点：138-141℃
元素分析：理论值C,33.04；H,3.74；N,11.56％；实测值C,33.01；H,3.72；N,11.65。
核磁：1H NMR(CDCl3):δ1.69(THF),2.57(s,12H,N(CH3)2),3.21(s,12H,N(CH3)2),3.76(THF),4.10(s,2H,NH),7.02-7.38(m,20H,Ph).13C NMR(CDCl3):δ25.61(THF),40.02,42.52(N(CH3)2),68.00(THF),122.18(p-CPh),122.37(m-CPh),129.71(o-CPh),148.00(Cipso-Ph),169.51(NCN)。
实施例2：
步骤1,五核锡(II)化合物a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0.015g(0.01mmol)的化合物a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25℃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80.4％。
实施例3：
步骤1,五核锡(II)化合物a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0.015g(0.01mmol)的化合物a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25℃反应2.0h,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84.6％。
实施例4：
步骤1,五核锡(II)化合物a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0.015g(0.01mmol)的化合物a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0.25h,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76.8％。
实施例5：
步骤1,五核锡(II)化合物a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0.015g(0.01mmol)的化合物a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91.0％。
实施例6：
步骤1,五核锡(II)化合物a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0.015g(0.01mmol)的化合物a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0.25h,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95.9％。
实施例7：
步骤1,五核锡(II)化合物a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0.015g(0.01mmol)的化合物a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0.5h,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97.3％。
Claims (4)
1.一种五核锡(II)化合物，其特征在于，结构式为：
2.如权利要求1所述的一种五核锡(II)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)氨基锂加入到反应容器中,加入乙醚溶解,在丙酮浴条件下加入二甲氨基腈，反应过夜,在丙酮浴条件下再加入SnCl2,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，得五核锡(II)化合物；所述的三甲基硅基苯(基)氨基锂、二甲氨基腈和SnCl2的摩尔比为1:1:1-1.25。
3.如权利要求2所述的一种五核锡(II)化合物的制备方法，其特征在于所述的三甲基硅基苯(基)氨基锂、二甲氨基腈和SnCl2的摩尔比为1:1:1.25。
4.如权利要求1所述的五核锡(II)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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| CN111187171B (zh) * | 2020-01-13 | 2022-11-11 | 山西大学 | 一种锡(ii)簇化合物及其制备方法和应用 |
| CN111153931A (zh) * | 2020-01-17 | 2020-05-15 | 山西大学 | 一种2-吡啶甲烷亚胺锡（ii）化合物及其制备方法和应用 |
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