CN112430241A - 一种六水合方酸钠配合物 - Google Patents
一种六水合方酸钠配合物 Download PDFInfo
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- -1 Sodium squarate hexahydrate Chemical class 0.000 title claims abstract description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims abstract description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000013078 crystal Substances 0.000 claims abstract description 11
- PWEBUXCTKOWPCW-UHFFFAOYSA-N squaric acid Chemical compound OC1=C(O)C(=O)C1=O PWEBUXCTKOWPCW-UHFFFAOYSA-N 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 8
- 239000000284 extract Substances 0.000 claims abstract description 8
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 239000003054 catalyst Substances 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 4
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 3
- 238000003756 stirring Methods 0.000 claims abstract description 3
- 238000007259 addition reaction Methods 0.000 claims abstract 2
- 238000000605 extraction Methods 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 238000002447 crystallographic data Methods 0.000 claims 1
- 239000003480 eluent Substances 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 230000005855 radiation Effects 0.000 claims 1
- WLURHQRAUSIQBH-UHFFFAOYSA-N sodium;hexahydrate Chemical compound O.O.O.O.O.O.[Na] WLURHQRAUSIQBH-UHFFFAOYSA-N 0.000 claims 1
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract 1
- 238000005303 weighing Methods 0.000 abstract 1
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 229910052763 palladium Inorganic materials 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910052684 Cerium Inorganic materials 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000002441 X-ray diffraction Methods 0.000 description 1
- 238000000429 assembly Methods 0.000 description 1
- 230000000712 assembly Effects 0.000 description 1
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 1
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 150000004696 coordination complex Chemical group 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001027 hydrothermal synthesis Methods 0.000 description 1
- NWYYWIJOWOLJNR-RXMQYKEDSA-N l-valinol Chemical compound CC(C)[C@H](N)CO NWYYWIJOWOLJNR-RXMQYKEDSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 150000002602 lanthanoids Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical group 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012450 pharmaceutical intermediate Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- UNUVOQUVNRHMOA-UHFFFAOYSA-L sodium squarate Chemical compound [Na+].[Na+].[O-]C1=C([O-])C(=O)C1=O UNUVOQUVNRHMOA-UHFFFAOYSA-L 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/04—Sodium compounds
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- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
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Abstract
一种如以下结构式(I)所示的六水合方酸钠配合物:
其合成方法是称取方酸0.6621g、甲酸铵2.6128g及无水甲醇100ml于250mL圆底烧瓶中，加热搅拌回流48h后，停止反应，再加入1M HCl溶液10mL，并用二氯甲烷3x15mL萃取，再将合并的萃取液用12M NaOH溶液15mL再次洗涤,并用二氯甲烷3x15mL再次萃取。将萃取液旋转蒸发并进行柱层析分离，得晶体配合物；该六水合方酸钠配合物(I)的用途，是将六水合方酸钠配合物(I)在苯甲醛与三甲基硅腈的加成反应中作为催化剂，并显示了一定的催化性能，其转化率达34.8％。
Description
一、技术领域
本发明涉及一种新化合物及用途，特别涉及一种钠配合物及其制备方法，确切地是一种六水合方酸钠配合物的制备及用途。
二、背景技术
方酸钠配合物是一种金属配合物。其类似的化合物已有文献报道。【1-2】由于是路易斯酸试剂，其用途可以研发作为有机催化剂及医药中间体。
参考文献：
1.Temperature Controlled Reversible Change of the Coordination Modesof the Highly Symmetrical Multitopic Ligand To Construct CoordinationAssemblies:Experimental and Theoretical Studies.Zheng,Bo；Dong,Hao；Bai,Junfeng；Li,Yizhi；Li,Shuhua；Scheer,Manfred，Journal of the American ChemicalSociety(2008),130,(25),7778-7779.
2.Lanthanide(III)squarates.2.High diversity of rare coordinationmodes of the squarate anion in a series of weakly hydrated cerium(III)squarates prepared by pseudo-hydrothermal methods,Trombe,Jean Christian；Petit,Jean Francois；Gleizes,Alain,Inorganica Chimica Acta(1990),167(1),69-81。
三、发明内容
本发明旨在提供一种六水合方酸钠配合物,所要解决的技术问题是一步合成得到目标产物。
本发明所称的六水合方酸钠配合物是由方酸与甲酸铵及氢氧化钠反应后制备的由以下化学式所示的化合物：
化学名称：六水合方酸钠配合物,简称配合物(I)。该化合物在苯甲醛的腈硅化反应中显示了较好的催化性能，其转化率达34.8％。
本合成方法包括合成和分离，所述的合成是方酸0.6621g、甲酸铵2.6128g及钯配合物0.0480g，溶于无水甲醇100ml中，加热搅拌回流48h后，停止反应，再加入1M HCl溶液10mL，并用二氯甲烷3x15mL萃取，再将合并的萃取液用12M NaOH溶液15mL再次洗涤,并用二氯甲烷3x15mL萃取。将合并的萃取液旋转蒸发并进行柱层析分离，得无色晶体配合物。
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。
该反应的反应机理可以推测为未反应的方酸与氢氧化钠作用，脱水，再钯催化剂作用下经过了一系列的变化，形成了钠配合物。
四、附图说明
图1是六水合方酸钠配合物的X-衍射分析图。
五、具体实施方式
1.钯配合物的制备：
(1)[1,4-(4R)-二异丙基－2－噁唑啉基]苯的制备
在100mL两口瓶中,无水无氧条件下,加入无水ZnCl21.4054g(10.64mmol),40ml氯苯,1,4-二氰基苯5.0236g(39.2mmol),L-缬氨醇16.2075g,将混合物在高温下回流60h,停止反应,减压以除去溶剂,,将剩余物用水溶解,并用CHCl3(20mLx2)萃取,有机相用无水硫酸钠干燥,旋转除去溶剂,将粗产品用石油醚/二氯甲烷(4:1)柱层析,得浅绿色粘稠状液体,产率52％；白色晶体,熔点:48-50℃,[a]5 D＝+111.9°(c＝0.429,CHCl3)；1HNMR(500MHz,CDCl3,27℃),δ(ppm)＝7.97(s,4H),4.39～4.43(t,3.18Hz,1H),4.09～4.15(m,2H),1.85～1.86(m,1H),(d,J＝6.24Hz,6H),0.86～0.96(d,J＝6.24Hz,6H).13CNMR 18.13,19.03,32.85,70.26,72.76,128.10,128.16,130.32,162.82.IR:3273,2976,2960,2932,2889,2869,1643,1512,1469,1408,1382,1366,1350,1320,1296,1276,1214,1180,1108,1077,1047,1014,971,955,900,891,838,726,698,675,659,540.HRMS(EI):m/z(％):calcd forC18H24N2O2:300.1838；found:300.1833。
(2)双{[1,4-(4S)-二异丙基－2－噁唑啉基苯]氯化钯}配合物的制备
100mL两口瓶中,无水无氧条件下,加入氯化钯1.5603g(4.92mmol),1,4-(4R)-二异丙基－2－噁唑啉基苯1.0435g(3.48mmol)，氯苯30mL将混合物在高温下回流48h,停止反应,减压以除去溶剂,,将剩余物三氯甲烷及乙醇溶解，自然挥发，得红褐色配合物得晶体，产率：92％；m.p.:>200℃,[a]5 D＝+512.8°(c 0.0564,CH3OH)；1H NMR(600MHz,CDCl3),δ`ppm8.81(s,8H,ArH),4.61-4.63(m,4H,CH×4),4.53(t,J＝9.6Hz,4H,CH×4),4.44(t,J＝8.5Hz,4H,CH×4),3.07-3.10(m,4H),1.18and 1.15(dd,J＝6.7,7.2Hz,24H,CH3×4)；13CNMR(150MHz,CDCl3)δppm 166.8,130.1(×2),129.3,72.0,69.1,30.7,19.0,15.6；νmax(cm-1)3487,3049,2957,2929,2872,1642,1609,1572,1509,1480,1464,1416,1379,1331,1288,1246,1178,1141,1123,1099,1045,1018,959,933,899,854,804,770,722,693,438；元素分析C36H48N4Cl4O4Pd2,测试值C 45.26％,H 5.06％,N 5.86％；理论值：C 45.32％,H 5.24％,N5.48％；
2.六水合方酸钠配合物的制备：
称取方酸0.6621g、甲酸铵2.6128g及钯配合物0.0480g，溶于无水甲醇100ml中，加热搅拌回流48h后，停止反应，再加入1M HCl溶液10mL，并用二氯甲烷3x15mL萃取，再将合并的萃取液用12M NaOH溶液15mL再次洗涤,并用二氯甲烷3x15mL再次萃取。将萃取液旋转蒸发并进行柱层析分离，得晶体配合物0.3852g，熔点：>250℃；元素分析数据：理论值：C:26.68％；H:2.80％；实测值：C:26.87％；H:2.63％；IR光谱数据：(KBr；v,cm-1):3347、3111、3032、2916、2849、1597、1539、1439、1393、1142、1078、880、825、710；化合物的晶体数据：
晶体典型的键长数据：
晶体的键角数据
3.腈硅化反应应用
0.05mmol化合物I,苯甲醛0.1mL,TMSCN 0.3ml(3.3mmol),2,相继在20～30℃下加入，20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,其转化率：34.8％；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)。
Claims (4)
1.一种六水合方酸钠配合物，其特征在于：由方酸与甲酸铵及氢氧化钠制备，由以下化学式表示的：
2.一种如权利要求1所述的六水合方酸钠晶体配合物(I)，在293(2)K温度下，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，其特征在于晶体属单斜晶系,空间群：C 2/c，其晶胞参数：
beta＝90deg；
gamma＝90deg。
3.一种如权利要求1所述的六水合方酸钠配合物(I)合成方法：包括合成、分离和纯化，所述的合成是称取方酸0.6621g、甲酸铵2.6128g及无水甲醇100ml于250mL圆底烧瓶中，加热搅拌回流48h后，停止反应，再加入1M HCl溶液10mL，并用二氯甲烷3x15mL萃取，再将合并的萃取液用12M NaOH溶液15mL再次洗涤,并用二氯甲烷3x15mL再次萃取。将萃取液旋转蒸发并将二氯甲烷与无水甲醇按体积比9:1为淋洗液进行柱层析分离，并收集最后组分点，得晶体配合物(I)。
4.一种如权利要求1所述的一种六水合钠配合物(I)的用途，其特征在于：将六水合方酸钠配合物作为催化剂在苯甲醛与三甲基硅腈的加成反应中作为催化剂，其转化率达34.8％。
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