CN106397462A - 3‑乙氧基水杨醛缩‑3‑氨基‑2‑羟基苯乙酮席夫碱四核铜配合物及合成方法 - Google Patents
3‑乙氧基水杨醛缩‑3‑氨基‑2‑羟基苯乙酮席夫碱四核铜配合物及合成方法 Download PDFInfo
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- 238000010189 synthetic method Methods 0.000 title claims abstract description 8
- 150000004699 copper complex Chemical class 0.000 title claims abstract description 7
- 239000002262 Schiff base Substances 0.000 title abstract description 4
- OFQBYHLLIJGMNP-UHFFFAOYSA-N 3-ethoxy-2-hydroxybenzaldehyde Chemical compound CCOC1=CC=CC(C=O)=C1O OFQBYHLLIJGMNP-UHFFFAOYSA-N 0.000 claims abstract description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- NLLYXOVHEQVWJF-UHFFFAOYSA-N 1-(3-amino-2-hydroxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(N)=C1O NLLYXOVHEQVWJF-UHFFFAOYSA-N 0.000 claims abstract description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 claims abstract description 5
- 238000010992 reflux Methods 0.000 claims abstract description 5
- 239000010949 copper Substances 0.000 claims description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 239000013078 crystal Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 abstract description 5
- 239000003446 ligand Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 238000010438 heat treatment Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- ZWVHTXAYIKBMEE-UHFFFAOYSA-N 2-hydroxyacetophenone Chemical compound OCC(=O)C1=CC=CC=C1 ZWVHTXAYIKBMEE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 230000003288 anthiarrhythmic effect Effects 0.000 description 1
- 239000003416 antiarrhythmic agent Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 229910001431 copper ion Inorganic materials 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229960002443 propafenone hydrochloride Drugs 0.000 description 1
- XWIHRGFIPXWGEF-UHFFFAOYSA-N propafenone hydrochloride Chemical compound Cl.CCCNCC(O)COC1=CC=CC=C1C(=O)CCC1=CC=CC=C1 XWIHRGFIPXWGEF-UHFFFAOYSA-N 0.000 description 1
- SMQUZDBALVYZAC-UHFFFAOYSA-N salicylaldehyde Chemical class OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 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
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/02—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of compounds containing imino groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/02—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups
- C07C251/24—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton containing imino groups having carbon atoms of imino groups bound to carbon atoms of six-membered aromatic rings
-
- 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)
Abstract
本发明公开了一种3‑乙氧基水杨醛缩‑3‑氨基‑2‑羟基苯乙酮席夫碱四核铜配合物[Cu4(ebyl)4]·2DMF及合成方法。该铜配合物即[Cu4(ebyl)4]·2DMF的分子式为：C74H74Cu4N6O18，分子量为：1589.55 g/mol,H2ebyl为3‑乙氧基水杨醛缩‑3‑氨基‑2‑羟基苯乙酮席夫碱。将1.662 g分析纯的3‑乙氧基水杨醛和1.512 g分析纯的3‑氨基‑2‑羟基苯乙酮，溶于30 mL分析纯乙醇溶液中，加热回流两个小时后得到配体H2ebyl。将0.073‑0.146 g干燥后的H2ebyl和0.040‑0.080 g分析纯乙酸铜溶于5‑10 mL分析纯DMF中，置于微反应瓶中，再加入5‑10 mL分析纯乙腈，置于80 oC烘箱五天。本发明工艺简单、成本低廉、化学组分易于控制、重复性好且产量高。
Description
技术领域
本发明涉及一种3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱四核铜配合物[Cu4(ebyl)4]·2DMF(H2ebyl为3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱)及合成方法。
背景技术
2-羟基苯乙酮是一种重要的有机和医药中间体，可用于合成IC类抗心律失常药—盐酸普罗帕酮，3-氨基-2-羟基苯乙酮本身具有很多配位原子，与水杨醛衍生物合成席夫碱之后，增加了其配位能力，可以和过渡金属配位，形成系列结构新颖、性质优良的配合物。
发明内容
本发明的目的就是利用微瓶反应方法合成3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱四核铜配合物即[Cu4(ebyl)4]·2DMF。
本发明涉及的[Cu4(ebyl)4]·2DMF的分子式为：C74H74Cu4N6O18，分子量为：1589.55g/mol,H2ebyl为3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱。晶体结构数据见表一,键长键角数据见表二。
表一：[Cu4(ebyl)4]·2DMF的晶体学参数
表二；[Cu4(ebyl)4]·2DMF的部分键长和键角(°)
| Cu2—O7 | 1.958(3) | Cu2—O6 | 1.912(3) |
| Cu2—O3 | 1.986(3) | Cu2—O4 | 2.353(3) |
| Cu2—N2 | 1.929(4) | Cu1—O2 | 1.915(3) |
| Cu1—O3 | 1.985(3) | Cu1—O14 | 1.989(3) |
| Cu1—O13 | 2.213(4) | Cu3—O7 | 2.012(3) |
| Cu1—N1 | 1.959(4) | Cu3—O11 | 1.958(3) |
| Cu3—O10 | 1.907(3) | Cu3—N3 | 1.951(4) |
| Cu3—O8 | 2.389(3) | Cu4—O11 | 1.996(3) |
| Cu4—O14 | 1.975(3) | Cu4—O15 | 1.887(4) |
| Cu4—O12 | 2.389(4) | Cu4—N4 | 1.923(4) |
| O7—Cu2—O3 | 88.13(12) | O3—Cu2—O4 | 75.12(12) |
| O7—Cu2—O4 | 96.81(13) | O6—Cu2—O7 | 176.67(14) |
| O6—Cu2—O3 | 93.23(13) | O6—Cu2—N2 | 85.05(17) |
| O6—Cu2—O4 | 86.48(14) | N2—Cu2—O7 | 93.19(16) |
| N2—Cu2—O3 | 171.99(14) | O3—Cu1—O14 | 88.58(12) |
| N2—Cu2—O4 | 112.51(14) | O3—Cu1—O13 | 97.98(13) |
| O2—Cu1—O3 | 167.76(15) | O2—Cu1—O13 | 94.14(15) |
| O2—Cu1—O14 | 94.23(14) | O2—Cu1—N1 | 84.42(15) |
| O14—Cu1—O13 | 84.89(14) | N1—Cu1—O14 | 176.44(15) |
| N1—Cu1—O3 | 92.07(14) | N1—Cu1—O13 | 98.49(15) |
| O7—Cu3—O8 | 73.30(12) | O11—Cu3—O8 | 98.43(13) |
| O11—Cu3—O7 | 89.20(13) | O10—Cu3—O7 | 94.60(13) |
| O10—Cu3—O11 | 174.42(15) | O10—Cu3—N3 | 83.64(17) |
| O10—Cu3—O8 | 86.60(14) | N3—Cu3—O7 | 173.33(16) |
| O11—Cu4—O12 | 73.74(13) | N3—Cu3—O11 | 92.13(16) |
| O14—Cu4—O11 | 88.09(13) | N3—Cu3—O8 | 112.93(15) |
| O14—Cu4—O12 | 100.45(13) | O15—Cu4—N4 | 95.17(19) |
| O15—Cu4—O11 | 93.38(15) | N4—Cu4—O11 | 168.28(16) |
| O15—Cu4—O14 | 175.59(15) | N4—Cu4—O14 | 82.81(17) |
| O15—Cu4—O12 | 83.95(15) | N4—Cu4—O12 | 115.13(15) |
| Cu2—O7—Cu3 | 110.85(14) | C11—O3—Cu2 | 119.5(3) |
| C28—O7—Cu2 | 125.0(3) | C11—O3—Cu1 | 125.4(3) |
| C28—O7—Cu3 | 121.9(3) | C4—O2—Cu1 | 113.2(3) |
| Cu1—O3—Cu2 | 110.86(13) | C21—O6—Cu2 | 112.9(3) |
| Cu3—O11—Cu4 | 111.04(14) | C55—O14—Cu1 | 131.6(3) |
| C45—O11—Cu3 | 123.6(3) | C55—O14—Cu4 | 112.9(3) |
| C45—O11—Cu4 | 120.7(3) | C38—O10—Cu3 | 114.5(3) |
| Cu4—O14—Cu1 | 114.33(16) | C29—O8—Cu3 | 110.0(3) |
| C33—O8—Cu3 | 132.5(3) | C16—O4—Cu2 | 131.8(4) |
| C53—O13—Cu1 | 129.5(4) | C43—N3—Cu3 | 125.6(4) |
| C12—O4—Cu2 | 108.4(3) | C39—N3—Cu3 | 111.0(3) |
| C46—O12—Cu4 | 108.5(3) | C9—N1—Cu1 | 125.2(4) |
| C46—O12—C50 | 115.9(5) | C5—N1—Cu1 | 110.8(3) |
| C50—O12—Cu4 | 130.9(4) | C26—N2—Cu2 | 125.6(4) |
| C62—O15—Cu4 | 127.2(4) | C22—N2—Cu2 | 110.9(4) |
| C56—N4—Cu4 | 112.8(3) | C60—N4—Cu4 | 123.6(5) |
所述[Cu4(ebyl)4]·2DMF的合成方法具体步骤为：
(1)将1.662g分析纯的3-乙氧基水杨醛和1.512g分析纯的3-氨基-2-羟基苯乙酮，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体H2ebyl。
(2)将0.073-0.146g干燥后的H2ebyl和0.040-0.080g分析纯乙酸铜溶于5-10mL分析纯二甲基甲酰胺(DMF)中，置于微反应瓶中，再加入5-10mL分析纯乙腈，置于80℃烘箱五天，有墨绿色块状晶体生成即[Cu4(ebyl)4]·2DMF。通过单晶衍射仪测定[Cu4(ebyl)4]·2DMF的结构，晶体结构数据见表一,键长键角数据见表二。
本发明具有工艺简单、成本低廉、化学组分易于控制、重复性好并产量高等优点。
附图说明
图1为本发明[Cu4(ebyl)4]·2DMF所用席夫碱配体的结构示意图。
图2为本发明[Cu4(ebyl)4]·2DMF的结构示意图。
图3为本发明[Cu4(ebyl)4]·2DMF中铜离子的配位模式示意图。
具体实施方式
实施例1：
本发明涉及的[Cu4(ebyl)4]·2DMF的分子式为：C74H74Cu4N6O18，分子量为：1589.55g/mol,H2ebyl为3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱。晶体结构数据见表一,键长键角数据见表二。
[Cu4(ebyl)4]·2DMF的合成方法具体步骤为：
(1)将1.662g分析纯的3-乙氧基水杨醛和1.512g分析纯的3-氨基-2-羟基苯乙酮，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体H2ebyl。
(2)将0.073g干燥后的H2ebyl和0.040g分析纯乙酸铜溶于5mL分析纯DMF中，置于微反应瓶中，再加入5mL分析纯乙腈，置于80℃烘箱五天，有墨绿色块状晶体生成即[Cu4(ebyl)4]·2DMF。产量0.041g，产率52.1％。通过单晶衍射仪测定[Cu4(ebyl)4]·2DMF的结构，晶体结构数据见表一,键长键角数据见表二。
实施例2：
本发明涉及的[Cu4(ebyl)4]·2DMF的分子式为：C74H74Cu4N6O18，分子量为：1589.55g/mol,H2ebyl为3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱。晶体结构数据见表一,键长键角数据见表二。
[Cu4(ebyl)4]·2DMF的合成方法具体步骤为：
(1)将1.662g分析纯的3-乙氧基水杨醛，1.512g分析纯的3-氨基-2-羟基苯乙酮，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体H2ebyl。
(2)将0.146g干燥后的H2ebyl和0.080g分析纯乙酸铜溶于10mL分析纯DMF中，置于微反应瓶中，再加入10mL分析纯乙腈，置于80℃烘箱五天，有墨绿色块状晶体生成即[Cu4(ebyl)4]·2DMF。产量0.087g，产率54.5％。通过单晶衍射仪测定[Cu4(ebyl)4]·2DMF的结构，晶体结构数据见表一,键长键角数据见表二。
Claims (1)
1.一种3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱四核铜配合物，其特征在于3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱四核铜配合物即[Cu4(ebyl)4]·2DMF的分子式为：C74H74Cu4N6O18，分子量为：1589.55g/mol,H2ebyl为3-乙氧基水杨醛缩-3-氨基-2-羟基苯乙酮席夫碱，晶体结构数据见表一,键长键角数据见表二；
表一：[Cu4(ebyl)4]·2DMF的晶体学参数
表二；[Cu4(ebyl)4]·2DMF的部分键长和键角°
所述[Cu4(ebyl)4]·2DMF的合成方法具体步骤为：
(1)将1.662g分析纯的3-乙氧基水杨醛和1.512g分析纯的3-氨基-2-羟基苯乙酮，溶于30mL分析纯乙醇溶液中，加热回流两个小时后得到配体H2ebyl；
(2)将0.073-0.146g干燥后的H2ebyl和0.040-0.080g分析纯乙酸铜溶于5-10mL分析纯二甲基甲酰胺中，置于微反应瓶中，再加入5-10mL分析纯乙腈，置于80℃烘箱五天，有墨绿色块状晶体生成即[Cu4(ebyl)4]·2DMF。
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| CN103804223A (zh) * | 2014-02-19 | 2014-05-21 | 桂林理工大学 | 2-羟基-3-(2-羟基-3-乙氧基亚苯甲胺)苯乙酮及合成方法 |
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| CN103804223A (zh) * | 2014-02-19 | 2014-05-21 | 桂林理工大学 | 2-羟基-3-(2-羟基-3-乙氧基亚苯甲胺)苯乙酮及合成方法 |
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| Title |
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| 李晓芳: "Schiff碱类过度金属配合物的合成、结构及生物活性研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 * |
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