CN106243015B - 一种2,6-吡啶二甲醇镍配合物晶体及用途 - Google Patents
一种2,6-吡啶二甲醇镍配合物晶体及用途 Download PDFInfo
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- CN106243015B CN106243015B CN201610560562.0A CN201610560562A CN106243015B CN 106243015 B CN106243015 B CN 106243015B CN 201610560562 A CN201610560562 A CN 201610560562A CN 106243015 B CN106243015 B CN 106243015B
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- 239000013078 crystal Substances 0.000 title claims abstract description 11
- -1 2, 6-pyridinedimethanol nickel Chemical compound 0.000 title abstract 2
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims abstract description 4
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims abstract 2
- 239000000126 substance Substances 0.000 claims description 3
- 230000005311 nuclear magnetism Effects 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229940125782 compound 2 Drugs 0.000 claims 1
- 238000002447 crystallographic data Methods 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 8
- WWFMINHWJYHXHF-UHFFFAOYSA-N [6-(hydroxymethyl)pyridin-2-yl]methanol Chemical compound OCC1=CC=CC(CO)=N1 WWFMINHWJYHXHF-UHFFFAOYSA-N 0.000 abstract description 8
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 abstract description 4
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 abstract description 4
- 238000001914 filtration Methods 0.000 abstract description 3
- 238000010992 reflux Methods 0.000 abstract description 3
- 238000003756 stirring Methods 0.000 abstract description 3
- 238000000926 separation method Methods 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000001308 synthesis method Methods 0.000 abstract 1
- 238000005303 weighing Methods 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 238000010189 synthetic method Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- 238000006555 catalytic reaction Methods 0.000 description 3
- BXGYYDRIMBPOMN-UHFFFAOYSA-N 2-(hydroxymethoxy)ethoxymethanol Chemical compound OCOCCOCO BXGYYDRIMBPOMN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- CWJWJOVKYKXSDU-UHFFFAOYSA-N methanol;nickel Chemical compound [Ni].OC.OC CWJWJOVKYKXSDU-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- XUEWIQNQPBSCOR-UHFFFAOYSA-N 2-nitro-1-phenylethanol Chemical class [O-][N+](=O)CC(O)C1=CC=CC=C1 XUEWIQNQPBSCOR-UHFFFAOYSA-N 0.000 description 1
- NCYCPEHRSPAKBM-LHHJGKSTSA-N CC1C(CCO[N](OCC(C)=N2)(O/C2=C/C=C)O2)=NC2=CC1 Chemical compound CC1C(CCO[N](OCC(C)=N2)(O/C2=C/C=C)O2)=NC2=CC1 NCYCPEHRSPAKBM-LHHJGKSTSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 150000001875 compounds Chemical class 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
- 238000000921 elemental analysis Methods 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000002815 nickel Chemical class 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
Classifications
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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
- C07D213/24—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 substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
- C07D213/30—Oxygen atoms
-
- 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
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2213—At least two complexing oxygen atoms present in an at least bidentate or bridging ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
-
- 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
- B01J2531/0238—Complexes comprising multidentate ligands, i.e. more than 2 ionic or coordinative bonds from the central metal to the ligand, the latter having at least two donor atoms, e.g. N, O, S, P
-
- 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
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/84—Metals of the iron group
- B01J2531/847—Nickel
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Pyridine Compounds (AREA)
- Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种2,6‑吡啶二甲醇镍配合物（I），其化学式如下：该配合物(I)的合成方法，包括合成和分离，其特征在于所述的合成是称取0.8200g(0.006mol)2,6‑吡啶二甲醇和0.7358g(0.003mol)NiCl2·6H2O放入100mL圆底烧瓶中，并加入30ml无水甲醇，搅拌使他们溶解，并加热回流48h；反应完成后，趁热过滤，使其自然挥发，几天后有绿色晶体析出；该配合物在苯甲醛与硝基甲烷制备目标产物时作为催化剂其反应的转化率达76.3%。
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的制备方法，确切地说是一种2,6-吡啶二甲醇镍配合物的制备及合成方法。
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手性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手性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。2,6-吡啶二甲醇镍配合物的合成方法已有文献报道，参考文献如下：
参考文献：
1.Syntheses and crystal structures of cobalt and nickel complexes of2,6- bis(hydroxymethyl)pyridine，Winter,Silke et al，Journal of CoordinationChemistry, 57(12),997-1014；2004
三、发明内容
本发明旨在提供一种2,6-吡啶二甲醇镍配合物的合成方法，所要解决的技术问题是一步合成手性2,6-吡啶二甲醇镍配合物。
本发明所称的2,6-吡啶二甲醇镍配合物的制备是一种是由2,6-吡啶二甲醇与六水合氯化镍制备的由以下化学式所示的配合物：
(Ⅰ)。
化学名称：2,6-吡啶二甲醇镍配合物，简称配合物(I)。
本合成方法包括合成和分离，所述的合成：称取 0.8200g(0.006mol)2,6-吡啶二甲醇和0.7358g(0.003mol)NiCl2·6H2O放入100mL 圆底烧瓶中，并加入30ml无水甲醇，搅拌使他们溶解，并加热回流48h。反应完成后，趁热过滤，使其自然挥发，几天后有绿色晶体析出。
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含1/2水分子2,6-吡啶二甲醇镍配合物的X-衍射分析图。
五、具体实施方式
称取0.8200g(0.006mol)2,6-吡啶二甲醇和0.7358g(0.003mol)NiCl2·6H2O放入100mL圆底烧瓶中，并加入30ml无水甲醇，搅拌使他们溶解，并加热回流48h。反应完成后，趁热过滤，使其自然挥发，几天后有绿色晶体析出；过滤后，用正己烷和石油醚将晶体洗涤3次，真空干燥，得目标产物0.40g，产率：33％；熔点：>200℃；元素分析数据[C14H19Cl2N2NiO4.5]：理论值(％)：C,40.33；H,4.59； N,6.72；实测值(％)：C,40.20；H,4.70；N,6.55；IR光谱数据(KBr；ν,cm-1)：2990, 1760,1590,1440,1180,1020,829,798,769。
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：
(三)、亨利反应应用
2-硝基-1-苯基乙醇
催化剂I(0.050mmol),苯甲醛0.10mL(0.986mmol)及硝基甲烷(0.50mL,9.255mmol)在室温下搅拌36h，用核磁监测，转化率:76.3％，1H NMR(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 (1)
1.一种有如下晶胞参数的化合物2,6-吡啶二甲醇镍配合物(I)的用途，该配合物在苯甲醛与硝基甲烷制备目标产物时作为催化剂：该配合物催化剂0.050mmol,苯甲醛0.10mL及硝基甲烷0.50mL,在室温下搅拌36h，用核磁监测，转化率:76.3％；其化学式如下：
该配合物(I)的晶胞参数如下：在100K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MoKα射线，以ω-θ扫描方式收集衍射数据，其特征在于三斜晶系,Cmce晶胞参数：α＝90°；β＝90°； γ＝90°。
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