CN105272890A - Open chain azathiacrown ether - Google Patents
Open chain azathiacrown ether Download PDFInfo
- Publication number
- CN105272890A CN105272890A CN201510731097.8A CN201510731097A CN105272890A CN 105272890 A CN105272890 A CN 105272890A CN 201510731097 A CN201510731097 A CN 201510731097A CN 105272890 A CN105272890 A CN 105272890A
- Authority
- CN
- China
- Prior art keywords
- open chain
- sulphur
- crown ether
- azepine
- azathiacrown
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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Abstract
The invention discloses an open chain azathiacrown ether compound. The structural formula of the open chain azathiacrown ether compound is as follows: (reference to the specification). The open chain azathiacrown ether compound is mainly used for heavy metal extraction and sensors.
Description
Technical field
The present invention relates to a kind of sulfide compound, particularly relate to a kind of open chain azepine sulphur crown ether.
Background technology
Open chain sulphur crown ether belongs to flexible ligand equally can complexation of metal ions with macrocyclic crown ether, and wherein the difference of end group and unit has different recognition reactions to metal ion, for the aspect such as selective extraction of heavy metal.The atom N had in the open chain azepine sulphur crown ether of center nitrogen replacement provides a reaction position, make it can other auxiliary molecule of functional group of scion grafting or utilize its grappling open chain azepine sulphur crown ether at material surface, as the detection moiety of sensor functional materials, usually regulate the kind of the kind of end group and the selective incubation metal of chain length adjustment metal ion; Expand its application in sensor, heavy metal identification.
Such as " Synthesisandmetal-ionbindingpropertiesofmonoazathiacrown ethers " JournalofOrgnanicChemistry [J] .2001,66 (21): 7008-7012) disclose 1 and 2 two kind of compound." Aselectiveturn-onfluorescentsensorforimagingcopperinlivi ngcells " JournalofOrgnanicChemistry [J] .2006, as heavy metal sensor molecule after the nitrogen-atoms of 128 (1): 10-11 utilizations on compound 2 is suitably modified.
The same with sulphur crown ether molecule with crown ether, open chain azepine sulphur crown ether and metal function degree depend on itself and metallic molecule size match to a great extent, namely its chain length is longer, more applicable large coordination bulk metal ion or metal cluster, so the open chain azepine sulphur crown ether above-mentioned 1,2 two kind of short chain is long and bulk metal ion and metal cluster interact poor.
Summary of the invention
In order to solve the deficiencies in the prior art, the invention provides a kind of molecular dimension larger, with bulk metal ion or the stronger open chain azepine sulphur crown ether of metal cluster effect.
Open chain azepine sulphur crown compound synthetic route of the present invention and reaction mechanism as follows:
2 '-second sulphur ethyl-2-mercapto ethyl thioether forms sulfydryl negative ion in the effect of alkali, then generates open chain azepine sulphur crown ether with the chlorine generation nucleophilic substitution on Dichloroethyl amine.
Open chain azepine sulphur crown compound of the present invention, structural formula is as follows:
The synthetic method of open chain azepine sulphur crown compound of the present invention, comprises the following steps:
In the reaction flask with magnetic agitation, thermometer, drying ethanol is added at 25 ~ 30 DEG C; after passing into nitrogen bubble; under nitrogen atmosphere protection; add 2 '-second sulphur ethyl-2-mercapto ethyl thioether and sodium hydroxide, after stirring 30min, under nitrogen atmosphere protection; add Dichloroethyl amine hydrochlorate; react seven days at 40 DEG C, by filtrate decompression evaporate to dryness after filtration, by recrystallizing methanol, filter, dry, obtain white solid open chain azepine sulphur crown ether.
Advantage of the present invention: the sulfide compound in documents is at most containing 5 haptos, 4 S-C
2h
4-unit; Open chain azepine sulphur crown ether molecule provided by the present invention provides 7 haptos, 6 S-C
2h
4-unit, and size is larger, hapto is more, have longer chain length, has stronger coordination with bulk metal ion or metal cluster.
Embodiment
Embodiment 1
Drying ethanol 50ml is being added with magnetic agitation, thermometer reaction flask at 25 ~ 30 DEG C; after passing into nitrogen bubble 20min; 2 '-second sulphur ethyl-2-mercapto ethyl thioether 0.99g and sodium hydroxide 0.33g is added in a nitrogen atmosphere under protection; after stirring 30min; Dichloroethyl amine hydrochlorate 0.42g is added in a nitrogen atmosphere under protection; react seven days at 40 DEG C, by filtrate decompression evaporate to dryness after filtration, by recrystallizing methanol, filter, dry.Obtain white solid, productive rate 20%.
Structural Identification:
Ultimate analysis:
Molecular formula: C
16h
35nS
6
Theoretical value: C, 44.29; H, 8.13; N, 13.70; S, 44.35
Measured value: C, 44.35; H, 7.92; N, 13.21
Infrared spectra (KBr, cm
-1): 3445,2927,2834,1424,1192,1142,1115,684
1HNMR(DMSO-d
6,δ/ppm)：δ1.18(t，6H)，1.94(br，1H)2.55(dd，4H)，2.62(t，4H)2.67-2.76(m，20H)，
13CNMR(DMSO-d
6，δ/ppm)：15.26，25.39，31.56,30.46,31.85,31.94,31.98,31.99，49.1。
Above-mentioned analytical data confirms that the material obtained by this synthetic method is open chain azepine sulphur crown ether really.
Claims (1)
1. an open chain azepine sulphur crown compound, its structural formula is as follows:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510731097.8A CN105272890A (en) | 2015-11-02 | 2015-11-02 | Open chain azathiacrown ether |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510731097.8A CN105272890A (en) | 2015-11-02 | 2015-11-02 | Open chain azathiacrown ether |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105272890A true CN105272890A (en) | 2016-01-27 |
Family
ID=55142791
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510731097.8A Pending CN105272890A (en) | 2015-11-02 | 2015-11-02 | Open chain azathiacrown ether |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105272890A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6187227B1 (en) * | 1998-06-02 | 2001-02-13 | Betzdearborn | Thiacrown ether compound corrosion inhibitors for alkanolamine units |
| CN1396944A (en) * | 2000-12-01 | 2003-02-12 | 东丽株式会社 | Polyester composition, films made thereof and process for producing the composition |
-
2015
- 2015-11-02 CN CN201510731097.8A patent/CN105272890A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6187227B1 (en) * | 1998-06-02 | 2001-02-13 | Betzdearborn | Thiacrown ether compound corrosion inhibitors for alkanolamine units |
| CN1396944A (en) * | 2000-12-01 | 2003-02-12 | 东丽株式会社 | Polyester composition, films made thereof and process for producing the composition |
Non-Patent Citations (2)
| Title |
|---|
| LI ZENG等: "A Selective Turn-On Fluorescent Sensor for Imaging Copper in Living Cells", 《J.AM.CHEM.SOC》 * |
| MUTSUO TANAKA等: "Synthesis and Metal-Ion Binding Properties of Monoazathiacrown Ethers", 《J.ORG.CHEM.》 * |
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Legal Events
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|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20160127 |
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| RJ01 | Rejection of invention patent application after publication |