CN106431972A - Acetophenone derivative Schiff base ligand H2brah and synthesis method - Google Patents

Acetophenone derivative Schiff base ligand H2brah and synthesis method Download PDF

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Publication number
CN106431972A
CN106431972A CN201610818110.8A CN201610818110A CN106431972A CN 106431972 A CN106431972 A CN 106431972A CN 201610818110 A CN201610818110 A CN 201610818110A CN 106431972 A CN106431972 A CN 106431972A
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China
Prior art keywords
brah
schiff base
base ligand
h2brah
analytically pure
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Chinese (zh)
Inventor
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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Priority to CN201610818110.8A priority Critical patent/CN106431972A/en
Publication of CN106431972A publication Critical patent/CN106431972A/en
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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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention discloses an acetophenone derivative Schiff base ligand H2brah and a synthesis method. The molecular formula of the ligand H2brah is C15H12BrNO3, the molecular weight is 334.17 g/mol, and H2brah is the 5-bromosalicylaldehyde-3-amino-2-hydroxy acetophenone Schiff base ligand. 2.010-4.020 g of analytically pure 5-bromosalicylaldehyde and 1.512-3.024 g of analytically pure 3-amino-2-hydroxy acetophenone are dissolved into 30-60 mL of analytically pure ethyl alcohol solution, and the Schiff base ligand H2brah is obtained after carrying out heating reflux for 2 hours. The synthesis method is simple in process, low in cost, high in repeatability and large in yield, and chemical components are easy to control.

Description

A kind of acetophenone derivs schiff base ligand H2Brah and synthetic method
Technical field
The present invention relates to a kind of acetophenone derivs schiff base ligand H2Brah and synthetic method.
Background technology
2- hydroxy acetophenone is a kind of important organic and medicine intermediate, can be used for synthesize IC class antiarrhymic- Propafenone hydrochloride, 3- amino -2- hydroxy acetophenone has a lot of coordination atoms in itself, synthesizes schiff bases with salicylaldehyde derivatives Afterwards, increased its coordination ability, can and transition-metal coordination, form that series structure is novel, the complex of good properties.
Content of the invention
The purpose of the present invention is H exactly using water-bath method synthesis acetophenone derivs schiff base ligand2brah.
H according to the present invention2The molecular formula of brah is：C15H12BrNO3, molecular weight is：334.17
G/mol, crystal structural data is shown in Table one, and bond distance's bond angle data is shown in Table two.
Table one：H2The crystallographic parameter of brah
Table two：H2The part bond distance of brahWith bond angle (°)
Br1-C5 1.899(3) C11-H11 0.9300
O2-H2 0.8200 C11-C12 1.403(4)
O2-C13 1.355(3) C11-C10 1.370(4)
C8-N1 1.410(4) C12-C14 1.473(4)
C8-C13 1.397(4) C9-H9 0.9300
C8-C9 1.388(4) C9-C10 1.373(5)
O1-H1 0.8200 C5-C4 1.383(4)
O1-C2 1.344(3) C14-C15 1.495(4)
O3-C14 1.229(4) C4-H4 0.9300
C1-C6 1.395(4) C4-C3 1.367(4)
C1-C7 1.447(4) C3-H3 0.9300
C1-C2 1.411(4) C3-C2 1.383(4)
N1-C7 1.281(4) C10-H10 0.9300
C6-H6 0.9300 C15-H15A 0.9600
C6-C5 1.369(4) C15-H15B 0.9600
C13-C12 1.396(4) C15-H15C 0.9600
C7-H7 0.9300
C13-O2-H2 109.5 C10-C9-H9 119.6
C13-C8-N1 115.7(2) C6-C5-Br1 120.1(2)
C9-C8-N1 126.2(3) C6-C5-C4 120.8(3)
C9-C8-C13 118.2(3) C4-C5-Br1 119.0(2)
C2-O1-H1 109.5 O3-C14-C12 120.6(3)
C6-C1-C7 120.3(3) O3-C14-C15 119.1(3)
C6-C1-C2 118.6(3) C12-C14-C15 120.3(3)
C2-C1-C7 121.1(3) C5-C4-H4 120.1
C7-N1-C8 123.8(2) C3-C4-C5 119.8(3)
C1-C6-H6 119.8 C3-C4-H4 120.1
C5-C6-C1 120.3(3) C4-C3-H3 119.6
C5-C6-H6 119.8 C4-C3-C2 120.8(3)
O2-C13-C8 116.9(3) C2-C3-H3 119.6
O2-C13-C12 121.6(3) O1-C2-C1 121.9(3)
C12-C13-C8 121.5(3) O1-C2-C3 118.4(3)
C1-C7-H7 119.7 C3-C2-C1 119.7(3)
N1-C7-C1 120.6(3) C11-C10-C9 121.0(3)
N1-C7-H7 119.7 C11-C10-H10 119.5
C12-C11-H11 119.9 C9-C10-H10 119.5
C10-C11-H11 119.9 C14-C15-H15A 109.5
C10-C11-C12 120.2(3) C14-C15-H15B 109.5
C13-C12-C11 118.2(3) C14-C15-H15C 109.5
C13-C12-C14 120.1(3) H15A-C15-H15B 109.5
C11-C12-C14 121.7(3) H15A-C15-H15C 109.5
C8-C9-H9 119.6 H15B-C15-H15C 109.5
C10-C9-C8 120.9(3)
Described H2The synthetic method of brah concretely comprises the following steps：
By analytically pure for 2.010-4.020g 5- bromosalicylaldehyde and 1.512-3.024g analytically pure 3- amino -2- hydroxy benzenes Ethyl ketone, is dissolved in 30mL-60mL analysis straight alcohol solution, obtains schiff base ligand H after being heated to reflux two hours2brah.Logical Cross single crystal diffractometer and measure H2The structure of brah, crystal structural data is shown in Table one, and bond distance's bond angle data is shown in Table two.
The present invention has the advantages that process is simple, with low cost, chemical constituent is easily controllable, reproducible and yield is high.
Brief description
Fig. 1 is H of the present invention2The synthetic route schematic diagram of brah.
Fig. 2 is H of the present invention2The structural representation of brah.
Specific embodiment
Embodiment 1：
H according to the present invention2The molecular formula of brah is：C15H12BrNO3, molecular weight is：334.17g/mol, H2Brah is 5- bromosalicylaldehyde contracting 3- amino -2- hydroxy acetophenone schiff base ligand, crystal structural data is shown in Table one, and bond distance's bond angle data is shown in Table Two.
H2The synthetic method of brah concretely comprises the following steps：
By analytically pure for 2.010g 5- bromosalicylaldehyde and 1.512g analytically pure 3- amino -2- hydroxy acetophenone, it is dissolved in In 30mL analysis straight alcohol solution, after being heated to reflux two hours, obtain schiff base ligand H2brah.Yield 3.208g, yield 96%.H is measured by single crystal diffractometer2The structure of brah, crystal structural data is shown in Table one, and bond distance's bond angle data is shown in Table two.
Embodiment 2：
H according to the present invention2The molecular formula of brah is：C15H12BrNO3, molecular weight is：334.17g/mol, H2Brah is 5- bromosalicylaldehyde contracting 3- amino -2- hydroxy acetophenone schiff base ligand, crystal structural data is shown in Table one, and bond distance's bond angle data is shown in Table Two.
H2The synthetic method of brah concretely comprises the following steps：
By the contracting of analytically pure for 4.020g 3,5- Dibromosalicylaldehyde and 3.024g analytically pure 3- amino -2- hydroxy acetophenone, It is dissolved in 60mL analysis straight alcohol solution, after being heated to reflux two hours, obtain part H2brah.Yield 6.483g, yield 97%.H is measured by single crystal diffractometer2The structure of brah, crystal structural data is shown in Table one, and bond distance's bond angle data is shown in Table two.

Claims (1)

1. a kind of acetophenone derivs schiff base ligand is it is characterised in that acetophenone derivs schiff base ligand is H2Brah divides Minor is：C15H12BrNO3, molecular weight is：334.17g/mol, crystal structural data is shown in Table one, and bond distance's bond angle data is shown in Table two；
Table one：H2The crystallographic parameter of brah
aR1=∑ | | Fo|-|Fc||/∑|Fo|.bwR2=[∑ w (| Fo 2|-|Fc 2|)2/∑w(Fo 2|)2]1/2
Table two：H2The part bond distance of brahWith bond angle °
Described H2The synthetic method of brah concretely comprises the following steps：
By analytically pure for 2.010-4.020g 5- bromosalicylaldehyde and 1.512-3.024g analytically pure 3- amino -2- hydroxy benzenes second Ketone, is dissolved in 30mL-60mL analysis straight alcohol solution, obtains schiff base ligand H after being heated to reflux two hours2brah.
CN201610818110.8A 2016-09-13 2016-09-13 Acetophenone derivative Schiff base ligand H2brah and synthesis method Pending CN106431972A (en)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0429157A (en) * 1990-05-24 1992-01-31 Mitsubishi Kasei Corp Electrostatic charge image developing toner
CN102304063A (en) * 2011-05-20 2012-01-04 桂林理工大学 Schiff base ligand and metal complex thereof and use of Schiff base ligand and metal complex thereof
CN103804223A (en) * 2014-02-19 2014-05-21 桂林理工大学 2-hydroxy-3-(2-hydroxy-3-ethyoxyl-N-methyl benzene) acetophenone and synthesis method thereof
CN103819358A (en) * 2014-02-19 2014-05-28 桂林理工大学 2-hydroxy-3-(2-hydroxy-3-methoxyl phenylene methanamine) acetophenone and synthesis method
CN103880706A (en) * 2014-03-28 2014-06-25 桂林理工大学 2-hydroxy-3-(2-hydroxy-3,5-dibromophenylenemethylamine)acetophenone and synthesis method

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH0429157A (en) * 1990-05-24 1992-01-31 Mitsubishi Kasei Corp Electrostatic charge image developing toner
CN102304063A (en) * 2011-05-20 2012-01-04 桂林理工大学 Schiff base ligand and metal complex thereof and use of Schiff base ligand and metal complex thereof
CN103804223A (en) * 2014-02-19 2014-05-21 桂林理工大学 2-hydroxy-3-(2-hydroxy-3-ethyoxyl-N-methyl benzene) acetophenone and synthesis method thereof
CN103819358A (en) * 2014-02-19 2014-05-28 桂林理工大学 2-hydroxy-3-(2-hydroxy-3-methoxyl phenylene methanamine) acetophenone and synthesis method
CN103880706A (en) * 2014-03-28 2014-06-25 桂林理工大学 2-hydroxy-3-(2-hydroxy-3,5-dibromophenylenemethylamine)acetophenone and synthesis method

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
张玲钰: "桥联多核金属配合物的制备与性质研究", 《中国优秀硕士学位论文全文数据库 工程科技I辑》 *
王娓: "钴、镍、铜基配合物的合成、晶体结构及性质研究", 《万方数据库》 *

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Application publication date: 20170222