CN108840821B - 一种钴配合物制备及其合成方法 - Google Patents
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- 150000004700 cobalt complex Chemical class 0.000 title claims abstract description 7
- 238000001308 synthesis method Methods 0.000 title abstract description 6
- 238000002360 preparation method Methods 0.000 title description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 26
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 24
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims abstract description 16
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000002825 nitriles Chemical class 0.000 claims abstract description 6
- 238000000034 method Methods 0.000 claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 15
- 238000003786 synthesis reaction Methods 0.000 abstract description 12
- 239000013078 crystal Substances 0.000 abstract description 11
- BRARRAHGNDUELT-UHFFFAOYSA-N 3-hydroxypicolinic acid Chemical compound OC(=O)C1=NC=CC=C1O BRARRAHGNDUELT-UHFFFAOYSA-N 0.000 abstract description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract description 6
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 239000003208 petroleum Substances 0.000 abstract description 4
- 239000000047 product Substances 0.000 abstract description 4
- 238000010992 reflux Methods 0.000 abstract description 4
- GVPFVAHMJGGAJG-UHFFFAOYSA-L cobalt dichloride Chemical compound [Cl-].[Cl-].[Co+2] GVPFVAHMJGGAJG-UHFFFAOYSA-L 0.000 abstract description 3
- 239000000706 filtrate Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- 238000005406 washing Methods 0.000 abstract description 3
- 238000001914 filtration Methods 0.000 abstract description 2
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000001291 vacuum drying Methods 0.000 abstract description 2
- 238000003756 stirring Methods 0.000 abstract 1
- 238000005303 weighing Methods 0.000 abstract 1
- 229910017052 cobalt Inorganic materials 0.000 description 7
- 239000010941 cobalt Substances 0.000 description 7
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 7
- 150000001414 amino alcohols Chemical class 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- WMLSNOBYCXQZGG-UHFFFAOYSA-N 2-phenyl-2-trimethylsilyloxypropanenitrile Chemical compound C[Si](C)(C)OC(C)(C#N)C1=CC=CC=C1 WMLSNOBYCXQZGG-UHFFFAOYSA-N 0.000 description 1
- 229910020676 Co—N Inorganic materials 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- PPOPKHRQSBWFTD-UHFFFAOYSA-L [O-]C(C1=NC=CC=C1O)=O.[O-]C(C1=NC=CC=C1O)=O.O.O.[Co+2] Chemical compound [O-]C(C1=NC=CC=C1O)=O.[O-]C(C1=NC=CC=C1O)=O.O.O.[Co+2] PPOPKHRQSBWFTD-UHFFFAOYSA-L 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 description 1
- 238000011914 asymmetric synthesis Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 150000001868 cobalt Chemical class 0.000 description 1
- GFHNAMRJFCEERV-UHFFFAOYSA-L cobalt chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Co+2] GFHNAMRJFCEERV-UHFFFAOYSA-L 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- LBFUKZWYPLNNJC-UHFFFAOYSA-N cobalt(ii,iii) oxide Chemical compound [Co]=O.O=[Co]O[Co]=O LBFUKZWYPLNNJC-UHFFFAOYSA-N 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
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- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2217—At least one oxygen and one nitrogen atom present as complexing atoms in an at least bidentate or bridging ligand
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
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- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
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- B01J2531/845—Cobalt
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Abstract
一种钴配合物，其化学式如下：
该钴配合物的合成方法，包括合成和分离，所述的合成是称取0.2000g3‑羟基‑2‑吡啶羧酸放入100mL圆底烧瓶中，加入50mL无水甲醇并搅拌使其溶解；将0.6842g氯化钴加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，滤液自然挥发，数天后有晶体析出；将晶体用石油醚和正己烷冲洗3次，真空干燥30min，得目标产物；该配合物在苯甲醛的腈硅化反应及苯甲醛与苯甲酰胺的反应中中显示了较好的催化性能，其转化率分别为68％及88％。
Description
一、技术领域
本发明涉及一种金属有机配位化合物(配合物)及其制备方法，特别涉及含氮的金属有机配合物及其制备方法，确切地说是一种钴配合物晶体及其合成方法。
二、背景技术
随着有机化学的发展,金属有机化合物在有机合成中的应用愈来愈广,是现在有机化学中极为活跃的领域之一,已经广泛应用于有机合成反应中。20世纪60年代后期出现的使用配体与过渡金属络合物催化的不对称合成反应大大加速了手性药物的研究。化学催化不对称合成法的重要内容便是配体及含金属催化剂的设计,从而使反应具有高效和高对映选择性。近年来钴金属配合物的合成有许多文献报道。参考文献【1-6】
1.Asymmetric hydrogenation catalyzed by bis(dimethylglyoximato)cobalt(II)-achiral base complex and chiral amino alcohol conjugatedsystems.Oxidoreductase model with enantioselectivity，Ohgo,Yoshiaki；Natori,Yukikazu；Takeuchi,Seiji；Yoshimura,Juji,Chemistry Letters(1974),(11),1327-30.
Synthesis,structure and acid-base properties of cobalt(III)complexeswith aminoalcohols tepanenko,O.N.；Reiter,L.G.Ukrainskii Khimicheskii Zhurnal(Russian Edition),(1992),58(12),1047-54.
3.Cobalt(III)mono-and trinuclear complexes with O,N-chelatingaminoalcohols apanadze,T.Sh.；Gulya,A.P.；Novotortsev,V.M.；Ellert,O.G.；Shcherbakov,V.M.；Kokunov,Yu.V.；Bushaev,Yu.
A.Koordinatsionnaya Khimiya(1991),17(7),934-40.
4.Magnetic properties of cobalt complexes with amino alcohols,Evreev,V.N.；Bogdanov,A.P.13Vses.Chugaev.Soveshch.po Khimii Kompleks.Soedin.,1978(1978),137.
5.Synthesis,stereochemistry,and reactions of cobalt(III)complexeswith amino alcohol ligands Okamoto,Martha S.No Corporate Source dataavailable|(1974),146pp.
6.Synthesis and properties of isomeric tris(N-[2-hydroxyethyl]ethylenediamine)cobalt(III)and tris(N-[2-hydroxypropyl]ethylenediamine)cobalt(III)chlorides,arpeiskaya,E.I.；Kukushkin,Yu.N.；Trofimov,V.A.；Yakovlev,I.P.,Zhurnal Neorganicheskoi Khimii(1971),16(7),1960-4。
三、发明内容
本发明旨在提供一种Co-N金属有机配合物以应用于催化领域，所要解决的技术问题遴选3-羟基-2-吡啶羧酸作为配体并合成钴配合物。
本发明所称的钴配合物一种是由3-羟基-2-吡啶羧酸与六水氯化钴制备的由以下化学式所示的配合物：
化学名称：二水合二[3-羟基-2-吡啶羧酸]钴(II)配合物，简称配合物(I)。该配合物在苯甲醛的腈硅化反应及苯甲醛与苯甲酰胺的反应中中显示了较好的催化性能，其转化率分别为68％及88％。。
本合成方法包括合成和分离，所述的合成是称取0.2000g3-羟基-2-吡啶羧酸放入100mL圆底烧瓶中，加入50mL无水甲醇并搅拌使其溶解；将0.6842g氯化钴加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，滤液自然挥发，数天后有晶体析出，将晶体用石油醚和正己烷冲洗3次，真空干燥30min，得目标产物。
合成反应如下：
合成方法一步得到目标产物，工艺简单，操作方便。
四、附图说明
图1钴(II)配合物的X-衍射分析图。
五、具体实施方式
称取0.2000g3-羟基-2-吡啶羧酸放入100mL圆底烧瓶中，加入50mL无水甲醇并搅拌使其溶解；将0.6842g氯化钴加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，滤液自然挥发，数天后有晶体析出。
将晶体用石油醚和正己烷冲洗3次，真空干燥30min，得目标产物，产率为70％，熔点大于220℃。元素分析数据C12H12CoN2O8，理论值：C：38.83％；H：3.26％；N：7.55％；C：38.60％；H：3.45％；N：7.14％红外光谱数据(KBr,cm-1)：4007；3946；3724；3256；1798；1605；1534；1413；1395；1311；1270；1173；951；789；741；
配合物晶体数据如下：
晶体典型的键长数据：
晶体典型的键角数据：
六、腈硅化反应应用
2-苯基-2-(三甲硅氧基)丙腈
0.2mmol化合物I,苯甲醛0.1mL,TMSCN 0.3ml(3.3mmol),2mL无水甲醇,相继在30～35℃下加入，72小时后，加入水淬灭经柱层后(石油醚/二氯甲烷：5/1)，得无色油状液体,转化率：67.6％；1H NMR(300MHz,CDCl3)7.56–7.59(m,0.9Hz,2H),7.31–7.34(m,3H),5.43(s,1H),0.16(s,9H).13C NMR(75MHz,CDCl3)136.1,128.8(x2),126.2(x2),119.1,63.5,-0.39(x3)。
七、苯甲醛与苯甲酰胺的反应
苯甲醛与苯甲酰胺的反应也是一种常用的有机合成反应，是合成酰胺的一种重要方法。在有机医药中间体方面也有广泛的应用。
实验的反应方程式：
在25mL两口瓶中,加入0.0659g配合物I,2mLTHF和氯苯2mL,0.05mL苯甲醛及0.1302g苯甲酰胺,回流反应24小时后,有晶体出现；进行1HNMR检测；催化转化率为88％。
Claims (1)
1.一种钴配合物的用途，其化学式如下：
其特征在于：所述的配合物I用于苯甲醛的腈硅化反应及苯甲醛与苯甲酰胺的反应中，其转化率分别为68％及88％，其中，苯甲醛的腈硅化反应及苯甲醛与苯甲酰胺的反应式分别如下：
苯甲醛的腈硅化反应：
苯甲醛与苯甲酰胺的反应：
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