CN105669710A - 一种铜配合物晶体的制备及其合成方法 - Google Patents
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- 239000013078 crystal Substances 0.000 title claims abstract description 20
- 150000004699 copper complex Chemical class 0.000 title claims abstract description 7
- 238000010189 synthetic method Methods 0.000 title claims abstract description 7
- 238000002360 preparation method Methods 0.000 title description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000001914 filtration Methods 0.000 claims abstract description 8
- IFOXWHQFTSCNQB-UHFFFAOYSA-N 5-aminopyridine-2-carbonitrile Chemical compound NC1=CC=C(C#N)N=C1 IFOXWHQFTSCNQB-UHFFFAOYSA-N 0.000 claims abstract description 5
- MPTQRFCYZCXJFQ-UHFFFAOYSA-L copper(II) chloride dihydrate Chemical compound O.O.[Cl-].[Cl-].[Cu+2] MPTQRFCYZCXJFQ-UHFFFAOYSA-L 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- 239000000126 substance Substances 0.000 claims abstract description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003208 petroleum Substances 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 238000001291 vacuum drying Methods 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 11
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 3
- 238000002447 crystallographic data Methods 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 238000005303 weighing Methods 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 2
- 238000011010 flushing procedure Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000010949 copper Substances 0.000 description 22
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000012937 correction Methods 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000006703 hydration reaction Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 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
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 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
- 238000010668 complexation reaction Methods 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000002050 diffraction method Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
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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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/08—Copper compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
Abstract
一种铜配合物晶体,其化学式如下：
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2-氰基-5-氨基吡啶铜配合物晶体的制备及其合成方法。
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.Asymmetrichydrogenationcatalyzedbybis(dimethylglyoximato)cobalt(II)-achiralbasecomplexandchiralaminoalcoholconjugatedsystems.Oxidoreductasemodelwithenantioselectivity，Ohgo,Yoshiaki;Natori,Yukikazu;Takeuchi,Seiji;Yoshimura,Juji,ChemistryLetters(1974),(11),1327-30.
Synthesis,structureandacid-basepropertiesofcobalt(III)complexeswithaminoalcoholstepanenko,O.N.;Reiter,L.G.UkrainskiiKhimicheskiiZhurnal(RussianEdition),(1992),58(12),1047-54.
3.Cobalt(III)mono-andtrinuclearcomplexeswithO,N-chelatingaminoalcoholsapanadze,T.Sh.;Gulya,A.P.;Novotortsev,V.M.;Ellert,O.G.;Shcherbakov,V.M.;Kokunov,Yu.V.;Bushaev,Yu.A.KoordinatsionnayaKhimiya(1991),17(7),934-40.
4.Magneticpropertiesofcobaltcomplexeswithaminoalcohols,Evreev,V.N.;Bogdanov,A.P.13Vses.Chugaev.Soveshch.poKhimiiKompleks.Soedin.,1978(1978),137.
5.Synthesis,stereochemistry,andreactionsofcobalt(III)complexeswithaminoalcoholligands
Okamoto,MarthaS.NoCorporateSourcedataavailable|(1974),146pp.
6.Synthesisandpropertiesofisomerictris(N-[2-hydroxyethyl]ethylenediamine)cobalt(III)andtris(N-[2-hydroxypropyl]ethylenediamine)cobalt(III)chlorides,arpeiskaya,E.I.;Kukushkin,Yu.N.;Trofimov,V.A.;Yakovlev,I.P.,ZhurnalNeorganicheskoiKhimii(1971),16(7),1960-4。
三、发明内容
本发明旨在提供一种Cu-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2-氰基5-氨基吡啶作为配体并合成铜配合物。
本发明所称的铜配合物一种是由2-氰基5-氨基吡啶与二水合氯化铜制备的由以下化学式所示的配合物：
（Ⅰ）。
化学名称：，一水合含一分子甲醇结晶的【5-氨基-吡啶亚酰胺乙酯】氯化铜（II）配合物，简称配合物(I)。
该配合物在苯甲醛的腈硅化反应中显示了较好的催化性能，其转化率为45%。
本合成方法包括合成和分离，所述的合成是称取0.5010g（0.0042mol）5-氨基-2-氰基吡啶放入100mL圆底烧瓶中，加入40mL无水乙醇并搅拌使其溶解；将1.4346g（0.0084mol）二水合氯化铜加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，得到滤渣，滤渣用无水甲醇溶解后过滤，三天后有绿色晶体析出。
将绿色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：
本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1一水合含一分子甲醇结晶的【5-氨基-吡啶亚酰胺乙酯】氯化铜（II）配合物配合物的X-衍射分析图。
五、具体实施方式
称取0.5010g（0.0042mol）5-氨基-2-氰基吡啶放入100mL圆底烧瓶中，加入40mL无水乙醇并搅拌使其溶解；将1.4346g（0.0084mol）二水合氯化铜加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，得到滤渣，滤渣用无水甲醇溶解后过滤，三天后有绿色晶体析出。
将绿色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42%，熔点158-162°C。元素分析数据C9H17Cl2CuN3O3，理论值：C：30.90%；H：4.86%；N：12.00%；实测值：C：31.39%；H：4.39%；N：12.42%；红外光谱数据(KBr,cm-1)：3425,3324,3218,1634,1590,1470,1423,1390,1311,1289,1147,1014,883,853,677,528,491.
配合物晶体数据如下：
经验式C9H17Cl2N3O3Cu
分子量349.69
温度293（2）K
波长0.71073?
晶系，空间群单斜晶系,P21/n
晶胞参数a=7.1949(9)?α=90°.
b=12.3806(16)?β=93.630（3）°.
c=15.758(2)?γ=90°.
体积1400.9（3）?^3
电荷密度4,1.658Mg/m^3
吸收校正参数1.943mm^-1
单胞内的电子数目716
晶体大小0.230x0.180x0.150mm
Theta角的范围2.094to26.000
HKL的指标收集范围-8<=h<=8,-14<k<15，-19<l<=17
收集/独立衍射数据8273/2754[R(int)=0.0341]
theta=30.5的数据完整度100.0%
吸收校正的方法多层扫描
最大最小的透过率0.7456and0.5930
精修使用的方法F^2的矩阵最小二乘法
数据数目/使用限制的数目/参数数目2754/6/190
精修使用的方法1.044
衍射点的一致性因子R1=0.0290，ωR2=0.0769
可观察衍射的吻合因子R1=0.0335,ωR2=0.0791
差值傅里叶图上的最大峰顶和峰谷0.458and-0.327e.?^-3
晶体典型的键长数据：
Cu(1)-N(2)1.960(2)
Cu(1)-N(1)2.0412(18)
Cu(1)-O(2)2.2542(18)
Cu(1)-Cl(2)2.2587(6)
Cu(1)-Cl(1)2.2833(7)
N(1)-C(1)1.320(3)
N(1)-C(5)1.346(3)
N(2)-C(6)1.261(3)
N(2)-H(2)0.813(16)
N(3)-C(2)1.347(3)
N(3)-H(3A)0.785(17)
N(3)-H(3B)0.837(17)
O(1)-C(6)1.321(3)
O(1)-C(7)1.448(3)
O(2)-C(9)1.398(3)
O(2)-H(2A)0.792(17)
O(3)-H(1B)0.816(19)
O(3)-H(1A)0.808(19)
C(1)-C(2)1.398(3)
C(1)-H(1)0.9300
C(2)-C(3)1.387(3)
C(3)-C(4)1.370(3)
C(3)-H(3)0.9300
C(4)-C(5)1.368(3)
C(4)-H(4)0.9300
C(5)-C(6)1.462(3)
C(7)-C(8)1.494(3)
C(7)-H(7A)0.9700
C(7)-H(7B)0.9700
C(8)-H(8A)0.9600
C(8)-H(8B)0.9600
C(8)-H(8C)0.9600
C(9)-H(9A)0.9600
C(9)-H(9B)0.9600
C(9)-H(9C)0.9600
晶体典型的键角数据：
N(2)-Cu(1)-N(1)80.05(8)
N(2)-Cu(1)-O(2)100.26(9)
N(1)-Cu(1)-O(2)84.29(7)
N(2)-Cu(1)-Cl(2)155.86(7)
N(1)-Cu(1)-Cl(2)92.31(5)
O(2)-Cu(1)-Cl(2)101.73(6)
N(2)-Cu(1)-Cl(1)93.15(6)
N(1)-Cu(1)-Cl(1)173.17(5)
O(2)-Cu(1)-Cl(1)96.48(6)
Cl(2)-Cu(1)-Cl(1)94.17(2)
C(1)-N(1)-C(5)119.44(19)
C(1)-N(1)-Cu(1)127.42(15)
C(5)-N(1)-Cu(1)112.97(14)
C(6)-N(2)-Cu(1)116.38(16)
C(6)-N(2)-H(2)121.0(19)
Cu(1)-N(2)-H(2)122.6(19)
C(2)-N(3)-H(3A)118(2)
C(2)-N(3)-H(3B)122.6(19)
H(3A)-N(3)-H(3B)116(3)
C(6)-O(1)-C(7)117.84(18)
C(9)-O(2)-Cu(1)127.90(18)
C(9)-O(2)-H(2A)111(2)
Cu(1)-O(2)-H(2A)112(2)
H(1B)-O(3)-H(1A)98(4)
N(1)-C(1)-C(2)122.7(2)
N(1)-C(1)-H(1)118.7
C(2)-C(1)-H(1)118.7
N(3)-C(2)-C(3)123.2(2)
N(3)-C(2)-C(1)119.9(2)
C(3)-C(2)-C(1)116.9(2)
C(4)-C(3)-C(2)120.1(2)
C(4)-C(3)-H(3)119.9
C(2)-C(3)-H(3)119.9
C(5)-C(4)-C(3)119.4(2)
C(5)-C(4)-H(4)120.3
C(3)-C(4)-H(4)120.3
N(1)-C(5)-C(4)121.5(2)
N(1)-C(5)-C(6)112.82(19)
C(4)-C(5)-C(6)125.7(2)
N(2)-C(6)-O(1)128.0(2)
N(2)-C(6)-C(5)117.7(2)
O(1)-C(6)-C(5)114.25(19)
O(1)-C(7)-C(8)107.0(2)
O(1)-C(7)-H(7A)110.3
C(8)-C(7)-H(7A)110.3
O(1)-C(7)-H(7B)110.3
C(8)-C(7)-H(7B)110.3
H(7A)-C(7)-H(7B)108.6
C(7)-C(8)-H(8A)109.5
C(7)-C(8)-H(8B)109.5
H(8A)-C(8)-H(8B)109.5
C(7)-C(8)-H(8C)109.5
H(8A)-C(8)-H(8C)109.5
H(8B)-C(8)-H(8C)109.5
O(2)-C(9)-H(9A)109.5
O(2)-C(9)-H(9B)109.5
H(9A)-C(9)-H(9B)109.5
O(2)-C(9)-H(9C)109.5
H(9A)-C(9)-H(9C)109.5
H(9B)-C(9)-H(9C)109.5
亨利反应应用
称取0.0453g（0.075mmol）配合物，置于25mL的小烧瓶中，加入1mLDMSO，再向溶液中加入0.05mL苯甲醛和0.25mL硝基甲烷，常温下搅拌反应10小时后，进行1HNMR检测转化率：87%；1HNMR(300MHz,CDCl3)7.28～7.32(m,5H,Ar-H),5.32～5.35(d,J=9.18Hz,1H,-CH),4.38～4.56(m,2H,-CH2),3.89(br,1H,-OH)。
Claims (3)
1.一种铜配合物晶体,其化学式如下：
（Ⅰ）。
2.权利要求1所述的配合物(I)，在293(2)K温度下，在牛津X-射线单晶衍射仪上，用经石墨单色器单色化的MoKa射线λ=0.71073?，以ω-θ扫描方式收集衍射数据，其特征在于晶体属单斜晶系,P21/n，a=7.1949(9)?α=90°；b=12.3806(16)?β=93.630°；c=15.758(2)?γ=90°。
3.权利要求1所述的配合物(I)的合成方法，包括合成和分离，其特征在于：称取0.5010g（0.0042mol）5-氨基-2-氰基吡啶放入100mL圆底烧瓶中，加入40mL无水乙醇并搅拌使其溶解；将1.4346g（0.0084mol）二水合氯化铜加入上述溶液，加热回流48h；反应结束后趁热过滤反应溶液，得到滤渣，滤渣用无水甲醇溶解后过滤，三天后有绿色晶体析出；将绿色晶体用石油醚和正己烷冲洗3次，真空干燥30min，得目标产物。
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