CN106431973A - 一种苯乙酮衍生物席夫碱配体H2etah及合成方法 - Google Patents

一种苯乙酮衍生物席夫碱配体H2etah及合成方法 Download PDF

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CN106431973A
CN106431973A CN201610818194.5A CN201610818194A CN106431973A CN 106431973 A CN106431973 A CN 106431973A CN 201610818194 A CN201610818194 A CN 201610818194A CN 106431973 A CN106431973 A CN 106431973A
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etah
schiff base
base ligand
h2etah
analytically pure
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张淑华
陈浩
张海洋
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Guilin University of Technology
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Guilin University of Technology
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    • 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
    • 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
    • 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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

本发明公开了一种苯乙酮衍生物席夫碱配体H2etah及合成方法。该配体即H2etah的分子式为：C17H17NO4，分子量为：299.32 g/mol,etah为3‑乙氧基水杨醛缩3‑氨基‑2‑羟基苯乙酮席夫碱配体。将1.662‑3.324 g分析纯的3‑乙氧基水杨醛和1.512‑3.024 g分析纯的3‑氨基‑2‑羟基苯乙酮，溶于30 mL‑60 mL分析纯乙醇溶液中，加热回流两个小时后得到席夫碱配体H2etah。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

一种苯乙酮衍生物席夫碱配体H2etah及合成方法
技术领域
本发明涉及一种苯乙酮衍生物席夫碱配体H2etah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水浴反应方法合成苯乙酮衍生物席夫碱配体即H2etah。
本发明涉及的H2etah的分子式为：C17H17NO4，分子量为：299.32g/mol，etah为3-乙氧基水杨醛缩3-氨基-2-羟基苯乙酮席夫碱配体，H2etah晶体结构数据见表一，键长键角数据见表二。
表-：H2etah的晶体学参数
表二：H2etah的部分键长和键角(°)
O3-H3 0.8200 C11-C12 1.381(4)
O3-C15 1.344(3) C17-H17A 0.9600
O4-C16 1.220(3) C17-H17B 0.9600
O2-H2 0.8200 C17-H17C 0.9600
O2-C8 1.350(3) C17-C16 1.508(4)
O1-C3 1.363(3) C13-H13 0.9300
O1-C2 1.425(3) C13-C12 1.369(4)
C15-C10 1.404(3) C3-C4 1.375(4)
C15-C14 1.401(3) C6-H6 0.9300
N1-C10 1.407(3) C6-C5 1.366(4)
N1-C9 1.286(3) C2-H2A 0.9700
C10-C11 1.379(4) C2-H2B 0.9700
C7-C9 1.446(4) C2-C1 1.488(4)
C7-C8 1.392(4) C12-H12 0.9300
C7-C6 1.403(3) C1-H1A 0.9600
C14-C16 1.465(4) C1-H1B 0.9600
C14-C13 1.401(3) C1-H1C 0.9600
C9-H9 0.9300 C4-H4 0.9300
C8-C3 1.402(4) C4-C5 1.386(4)
C11-H11 0.9300 C5-H5 0.9300
C15-O3-H3 109.5 O4-C16-C17 118.5(2)
C8-O2-H2 109.5 C14-C16-C17 120.8(3)
C3-O1-C2 118.3(2) C14-C13-H13 119.4
O3-C15-C10 116.7(2) C12-C13-C14 121.1(3)
O3-C15-C14 123.1(2) C12-C13-H13 119.4
C14-C15-C10 120.2(2) O1-C3-C8 115.1(2)
C9-N1-C10 121.5(2) O1-C3-C4 125.7(3)
C15-C10-N1 117.0(2) C4-C3-C8 119.2(3)
C11-C10-C15 119.1(2) C7-C6-H6 119.9
C11-C10-N1 123.8(2) C5-C6-C7 120.2(3)
C8-C7-C9 121.1(2) C5-C6-H6 119.9
C8-C7-C6 119.6(3) O1-C2-H2A 110.1
C6-C7-C9 119.2(3) O1-C2-H2B 110.1
C15-C14-C16 120.6(2) O1-C2-C1 108.0(2)
C15-C14-C13 118.5(2) H2A-C2-H2B 108.4
C13-C14-C16 120.9(2) C1-C2-H2A 110.1
N1-C9-C7 121.9(2) C1-C2-H2B 110.1
N1-C9-H9 119.1 C11-C12-H12 120.1
C7-C9-H9 119.1 C13-C12-C11 119.8(3)
O2-C8-C7 122.3(2) C13-C12-H12 120.1
O2-C8-C3 118.0(2) C2-C1-H1A 109.5
C7-C8-C3 119.7(2) C2-C1-H1B 109.5
C10-C11-H11 119.4 C2-C1-H1C 109.5
C10-C11-C12 121.2(2) H1A-C1-H1B 109.5
C12-C11-H11 119.4 H1A-C1-H1C 109.5
H17A-C17-H17B 109.5 H1B-C1-H1C 109.5
H17A-C17-H17C 109.5 C3-C4-H4 119.3
H17B-C17-H17C 109.5 C3-C4-C5 121.3(3)
C16-C17-H17A 109.5 C5-C4-H4 119.3
C16-C17-H17B 109.5 C6-C5-C4 119.9(3)
C16-C17-H17C 109.5 C6-C5-H5 120.1
O4-C16-C14 120.7(3) C4-C5-H5 120.1
所述H2etah的合成方法具体步骤为：
将1.662-3.324g分析纯的3-乙氧基水杨醛和1.512-3.024g分析纯的3-氨基-2-羟基苯乙酮，溶于30mL-60mL分析纯乙醇溶液中，加热回流两个小时后得到席夫碱配体H2etah。通过单晶衍射仪测定H2etah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H2etah的合成路线示意图。
图2为本发明H2etah的结构示意图。
具体实施方式
实施例1：
本发明涉及的H2etah的分子式为：C17H17NO4，分子量为：299.32g/mol，H2etah为3-乙氧基水杨醛缩3-氨基-2-羟基苯乙酮席夫碱配体，晶体结构数据见表一，键长键角数据见表二。
H2etah的合成方法具体步骤为：
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席夫碱配体etah。产量2.873g，产率96％。通过单晶衍射仪测定H2etah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H2etah的分子式为：C17H17NO4，分子量为：299.32g/mol，H2etah为3-乙氧基水杨醛缩3-氨基-2-羟基苯乙酮席夫碱配体，晶体结构数据见表一，键长键角数据见表二。
H2etah的合成方法具体步骤为：
将3.324g分析纯的3-乙氧基水杨醛和3.024g分析纯的3-氨基-2-羟基苯乙酮，溶于60mL分析纯乙醇溶液中，加热回流两个小时后得到配体H2etah。产量5.807g，产率97％。通过单晶衍射仪测定H2etah的结构，晶体结构数据见表一，键长键角数据见表二。

Claims (1)

1.一种苯乙酮衍生物席夫碱配体即H2etah，其特征在于苯乙酮衍生物席夫碱配体即H2etah的分子式为：C17H17NO4，分子量为：299.32g/mol，etah为3-乙氧基水杨醛缩3-氨基-2-羟基苯乙酮席夫碱配体，H2etah晶体结构数据见表一，键长键角数据见表二；
表一：H2etah的晶体学参数
表二：H2etah的部分键长和键角°
所述H2etah的合成方法具体步骤为：
将1.662-3.324g分析纯的3-乙氧基水杨醛和1.512-3.024g分析纯的3-氨基-2-羟基苯乙酮，溶于30mL-60mL分析纯乙醇溶液中，加热回流两个小时后得到席夫碱配体H2etah。
CN201610818194.5A 2016-09-13 2016-09-13 一种苯乙酮衍生物席夫碱配体H2etah及合成方法 Pending CN106431973A (zh)

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Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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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Application publication date: 20170222