CN105061516A - 一种钯配合物的合成方法及用途 - Google Patents
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 229910052763 palladium Inorganic materials 0.000 title claims abstract description 10
- 238000010189 synthetic method Methods 0.000 title claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000013078 crystal Substances 0.000 claims abstract description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000000243 solution Substances 0.000 claims abstract description 8
- 239000000047 product Substances 0.000 claims abstract description 7
- 238000003756 stirring Methods 0.000 claims abstract description 6
- 239000000706 filtrate Substances 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000010992 reflux Methods 0.000 claims abstract description 4
- 239000012047 saturated solution Substances 0.000 claims abstract description 4
- 238000001291 vacuum drying Methods 0.000 claims abstract description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- -1 phenyl aldehyde Chemical class 0.000 claims description 6
- 238000003786 synthesis reaction Methods 0.000 claims description 6
- 230000009466 transformation Effects 0.000 claims description 4
- 230000003197 catalytic effect Effects 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 abstract description 4
- 229910052710 silicon Inorganic materials 0.000 abstract description 2
- 239000010703 silicon Substances 0.000 abstract description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 229910021120 PdC12 Inorganic materials 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- 238000006842 Henry reaction Methods 0.000 abstract 1
- 238000006555 catalytic reaction Methods 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- 238000011010 flushing procedure Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 238000005303 weighing Methods 0.000 abstract 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 7
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QMXOFBXZEKTJIK-UHFFFAOYSA-N Glycinol Natural products C1=C(O)C=C2OCC3(O)C4=CC=C(O)C=C4OC3C2=C1 QMXOFBXZEKTJIK-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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- MGHPNCMVUAKAIE-UHFFFAOYSA-N diphenylmethanamine Chemical compound C=1C=CC=CC=1C(N)C1=CC=CC=C1 MGHPNCMVUAKAIE-UHFFFAOYSA-N 0.000 description 2
- PYNLOHHOFAKTCE-UHFFFAOYSA-N diphenylmethanamine;dihydrochloride Chemical compound Cl.Cl.C=1C=CC=CC=1C(N)C1=CC=CC=C1 PYNLOHHOFAKTCE-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 1
- 0 C*(NCC1C=CC=CC=C1)(Cl)I Chemical compound C*(NCC1C=CC=CC=C1)(Cl)I 0.000 description 1
- 238000006716 Hiyama reaction Methods 0.000 description 1
- 235000017848 Rubus fruticosus Nutrition 0.000 description 1
- 244000172730 Rubus fruticosus Species 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000007333 cyanation reaction 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
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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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
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/006—Palladium compounds
- C07F15/0066—Palladium compounds without a metal-carbon linkage
-
- 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
- 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
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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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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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
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/34—Other additions, e.g. Monsanto-type carbonylations, addition to 1,2-C=X or 1,2-C-X triplebonds, additions to 1,4-C=C-C=X or 1,4-C=-C-X triple bonds with X, e.g. O, S, NH/N
- B01J2231/341—1,2-additions, e.g. aldol or Knoevenagel condensations
- B01J2231/342—Aldol type reactions, i.e. nucleophilic addition of C-H acidic compounds, their R3Si- or metal complex analogues, to aldehydes or ketones
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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
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
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- 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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- Organic Chemistry (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
一种有如下结构式(I)的钯配合物,该配合物的合成方法,是用0.03mol?L-苯甘氨酸4.5291g放入100ml的圆底烧瓶中,加入40ml无水甲醇并搅拌使其溶解,称取0.01mol?PdCl2(1.7633g)加入上述溶液,加热回流反应48h。反应结束后趁热过滤反应溶液,得到饱和溶液,滤液自然挥发,两天后析出黄色晶体。将黄色晶体用二氯甲烷、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(I)在苯甲醛的腈硅化反应及亨利反应中显示了良好的催化性能,其转化率分别达49%及83%。
Description
技术领域
本发明涉及一种化合物,特别涉及一种配合物,确切地说是一种钯配合物的合成方法及用途。
背景技术
钯配合物是重要的催化剂和医药化工产品,其合成方法已有相关文献报道。【1-3】参考文献:
参考文献:
1.Newpreparationoftridentatebis-oxazolinecarbazoleligandeffectiveforenantioselectiveNozaki-Hiyamareaction.Inoue,Masahiro;Nakada,Masahisa.,Heterocycles(2007),72133-138.
2.HighlyenantioselectiveheteroDiels-AlderreactionsofN-sulfinyldienophilespromotedbycopper(II)-andzinc(II)-chiralbis(oxazoline)complexes.Bayer,Annette;Gautun,OddR.Tetrahedron:Asymmetry(2001),12(21),2937-2939.
3.Bis(oxazoline)-metalcomplexesimmobilizedbyelectrostaticinteractionsasheterogeneouscatalystsforenantioselectiveDiels-Alderreactions.Fraile,J.M.;Garcia,J.I.;Harmer,M.A.;Herrerias,C.I.;Mayoral,J.A.JournalofMolecularCatalysisA:Chemical(2001),165(1-2),211-218.
4.Useofbis(oxazoline)-metalcomplexesaschiralcatalystsforasymmetricDiels-Alderreactionsusing2-acetyl-1,4-naphthoquioneasadienophile.Brimble,MargaretA.;McEwan,JohnF.Sch.Chem.,Univ.Sydney,Sydney,Australia.Tetrahedron:Asymmetry(1997),8(24),4069-4078.
5.Enantioselectiveallylationofaldehydespromotedbychiralzincbis(oxazoline)complexes.Cozzi,PierGiorgio;Orioli,Paolo;Tagliavini,Emilio;Umani-Ronchi,Achille.TetrahedronLetters(1997),38(1),145-148.
申请人在L-苯甘氨酸和氯化钯反应合成钯配合物的过程中,未得到L-苯甘氨酸和氯化钯配合物,而是到了另一种苯甲胺氯化钯配合物。
发明内容
本发明旨在提供二苯甲胺氯化钯配合物。所要解决的技术问题是一步合成得到目标产物。
本发明所称的钯配合物是由氯化钯与L-苯甘氨醇制备的由以下化学式所示的化合物:
化学名称:二苯甲胺氯化钯配合物,简称配合物(I)。
本合成方法包括合成和分离,所述的合成0.03molL-苯甘氨酸4.5291g放入100ml的圆底烧瓶中,加入40ml无水甲醇并搅拌使其溶解,称取0.01molPdCl2(1.7633g)加入上述溶液,加热回流反应48h。反应结束后趁热过滤反应溶液,得到饱和溶液,滤液自然挥发,两天后析出黄色晶体。将黄色晶体用二氯甲烷、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。
该配合物在苯甲醛的亨利反应、腈硅化反应中显示了良好的的催化性能,其转化率分别达49%及83%。
其反应机理可推测如下:
L-苯甘氨醇在氯化钯的作用下,脱去羧酸分子,并形成了二氯化二苯甲胺钯配合物。
附图说明
图1二氯化二苯甲胺钯配合物的X-衍射分析图。
具体实施方式
称取0.03molL-苯甘氨酸(4.5291g)放入100ml的圆底烧瓶中,加入40ml无水甲醇并搅拌使其溶解,称取0.01molPdCl2(1.7633g)加入上述溶液,加热回流反应48h。反应结束后趁热过滤反应溶液,得到饱和溶液,滤液自然挥发,两天后析出黄色晶体;
将黄色晶体用二氯甲烷、石油醚和正己烷冲洗3次,真空干燥30min,得目标产物,产率为38%,熔点128-130℃,元素分析数据[Pd(C14H16N2)]Cl2,理论值:C:42.94%;H:4.63%;N:7.15%;实测值:C:43.16%;H:4.34%;N:7.19%;红外光谱数据(KBr,cm-1):478,504,593,698,729,848,924,971,1028,1052,1171,1239,1351,1392,1439,1456,1498,1587,1738,2617,2953,3033,3063,3111,3214;
其晶体数据如下:
晶体典型的键长数据:
晶体典型的键角数据:
Henry反应应用
2-硝基-1苯基乙醇的制备
称取0.0636g(0.15mmol)配合物,置于5ml圆底烧瓶中,加入2mlDMSO,再向溶液加入0.1ml苯甲醛和0.5ml硝基甲烷,常温搅拌反应24h,进行1HNMR检测,转化率为49%;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);
硅腈化反应应用:
称取0.0402g(0.1mmol)单晶,置于25ml小烧瓶中,加入2mlDMSO,再向溶液中加入0.1ml苯甲醛和0.3ml三甲基硅腈,常温下搅拌72h,进行1HNMR检测。转化率为83%;1HNMR(300MHz,CDCl3)7.56–7.59(m,0.9Hz,2H),7.31–7.34(m,3H),5.43(s,1H),0.16(s,9H).13CNMR(75MHz,CDCl3)136.1,128.8(x2),126.2(x2),119.1,63.5,-0.39(x3)。
Claims (2)
1.一种有如下结构式的钯配合物,该配合物的合成方法,包括合成和分离,其特征在于:所述的合成0.03molL-苯甘氨酸放入100ml的圆底烧瓶中,加入40ml无水甲醇并搅拌使其溶解,称取0.01molPdCl2加入上述溶液,加热回流反应48h,反应结束后趁热过滤反应溶液,得到饱和溶液,滤液自然挥发,两天后析出黄色晶体;将黄色晶体用二氯甲烷、石油醚和正己烷冲洗3次,真空干燥30min,得目标产物;
2.权利要求1所述的配合物(I)在苯甲醛的腈硅化反应及亨利反应中显示了良好的催化性能,其转化率分别达49%及83%。
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Cited By (2)
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CN105541920A (zh) * | 2015-12-04 | 2016-05-04 | 罗梅 | 一种手性(R)-α-苯乙胺铂配合物晶体 |
CN108291306A (zh) * | 2015-11-27 | 2018-07-17 | 埃托特克德国有限公司 | 用于钯的化学浸镀的镀浴组合物和方法 |
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN108291306A (zh) * | 2015-11-27 | 2018-07-17 | 埃托特克德国有限公司 | 用于钯的化学浸镀的镀浴组合物和方法 |
CN108291306B (zh) * | 2015-11-27 | 2019-12-27 | 埃托特克德国有限公司 | 用于钯的化学浸镀的镀浴组合物和方法 |
CN105541920A (zh) * | 2015-12-04 | 2016-05-04 | 罗梅 | 一种手性(R)-α-苯乙胺铂配合物晶体 |
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