CN103613570A - Fluorescent organic compound 3-chloroindene lactone and synthetic method thereof - Google Patents

Fluorescent organic compound 3-chloroindene lactone and synthetic method thereof Download PDF

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Publication number
CN103613570A
CN103613570A CN201310681241.2A CN201310681241A CN103613570A CN 103613570 A CN103613570 A CN 103613570A CN 201310681241 A CN201310681241 A CN 201310681241A CN 103613570 A CN103613570 A CN 103613570A
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lactone
indenes
chlorine
chloro
organic compound
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李平
李霞
封康
史小凤
李纳
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Tianjin University of Technology
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Tianjin University of Technology
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
    • C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

The invention discloses fluorescent organic compound 3-chloroindene lactone and a synthetic method thereof. 3-chloroindene lactone is synthesized by using 3-chloro phthalic anhydride and succinic acid as raw materials, and has a structural formula shown in the specification. The synthetic method comprises a step of mixing 3-chloro phthalic anhydride with succinic acid to prepare 3-chloro indene lactone. 3-chloro indene lactone is a fluorescent organic compound and is a novel fluorescent compound, and can be applied to the field of fluorescence labeling.

Description

Fluorescence organic compound 3-chlorine connects indenes lactone and synthetic method
Technical field
The invention belongs to organic materials synthesis technical field, particularly a kind of organic compound and synthetic method thereof with fluorescence property.
Background technology
Traditional biological label method comprises radioisotope method and fluorescence labeling method.Radio isotope can produce radiation to organism, and to environment, and radio isotope has the transformation period of himself, signal can be more and more a little less than, so the method now oneself through gradually being abandoned by people.And signal to noise ratio is high, the fluorescence labeling technology that sensitivity is good has been widely used in biological and medical aspect, in Front Fields of Life Sciences fields such as biochip, protein analysis, DNA sequencing, fluoroimmunoassay, fluidic cell measurement, clinical analysis of diagnosis and treatments, plays an important role [1-2].Therefore, novel fluorescent compound is synthetic significant.Synthesizing of double-colored alkene diketone [3]comparatively perfect work has been done by Structural Identification and this seminar of Ultraluminescence performance test, its thundering stoke shift and have huge realistic meaning and using value widely at aspects such as environmental monitoring, life science, medical diagnosiss with the good complex performance of metal ion, is worth us further to further investigate.Yet the Structural Identification that connects indenes lactone for double-colored alkene diketone precursor, and the test of ultraviolet, fluorescence property, up to the present, there are no report.
Summary of the invention
The object of the invention is to provide a kind of novel fluorescence organic compound, and 3-chlorine connects indenes lactone and synthetic method thereof.
Fluorescence organic compound 3-chlorine provided by the invention connects indenes lactone, and its structural formula is:
Figure BDA0000435212500000011
Above-mentioned 3-chlorine connects the synthetic method of indenes lactone, comprising:
Synthetic route:
Figure BDA0000435212500000021
Concrete synthesis step is as follows:
Thermometer is being housed, in reflux exchanger and churned mechanically four-hole bottle, is adding 3-chloro-phthalic anhydride and succinic acid (mol ratio is 1:1～2), be warming up to 210 ℃.Start stirring, add potassium acetate (mol ratio of potassium acetate and 3-chloro-phthalic anhydride is 0.2～0.35:1), 210 ℃ are reacted 2～4 hours.Then be cooled to 100 ℃, add hot water and import water vapour.Until reaction product forms broken particle, filter, use hot water wash product, dry, with ethanol, boil to remove resinous impurities.Refilter, with ethanol wash elutant colourless till, dry, obtain micro-reddish yellow powder, be 3-chlorine and connect ester mixture in indenes; After twice recrystallization of oil of mirbane, obtain faint yellow solid powder, 3-chlorine connects indenes lactone.
Structural characterization data:
1HNMR(400MHz，CDCl 3）：7.55-7.91(m，6H)，6.89（m，2H）
IR(KBr，cm -1)：3085.27,3052.36，1785.62,1650.54,1618.36,1471.72,992.08,763.66,706.39
MS：m/z358.0(M +)
In UV(methyl alcohol): λ max=385.0nm
In FL(methyl alcohol): λ ex=385.0nm, emission wavelength lambda em=443.0nm.
Advantage of the present invention and positively effect:
It is a kind of novel fluorescence organic compound that organic compound 3-chlorine provided by the invention connects indenes lactone, has fluorescence property.
Fluorescence organic compound provided by the invention can be used for fluorescent mark biological field; And the field such as environmental monitoring, life science, medical diagnosis.
Embodiment
Embodiment 1
Thermometer is being housed, in reflux exchanger and churned mechanically four-hole bottle, is adding 3-chloro-phthalic anhydride 30.5g (0.167mol) and succinic acid (in molar ratio for 1:1 adds), be warming up to 210 ℃.Start stirring, add potassium acetate (0.033mol), 210 ℃ are reacted 2.5 hours.Then be cooled to 100 ℃, add hot water and import water vapour.Until reaction product forms broken particle, filter, use hot water wash product, dry, with ethanol, boil to remove resinous impurities.Refilter, with ethanol wash elutant colourless till, dry, obtain micro-reddish yellow powder 18.3g, be 3-chlorine and connect ester mixture in indenes; After twice recrystallization of oil of mirbane, obtain faint yellow solid powder, 3-chlorine connects indenes lactone 4.0g, yield 6.7 ﹪.m.p.350～351℃。
Embodiment 2
Thermometer is being housed, in reflux exchanger and churned mechanically four-hole bottle, is adding 3-chloro-phthalic anhydride 30.5g (0.167mol) and succinic acid (mol ratio is 1:1.5), be warming up to 210 ℃.Start stirring, add potassium acetate (0.05mol), 210 ℃ are reacted 2.5 hours.Then be cooled to 100 ℃, add hot water and import water vapour.Until reaction product forms broken particle, filter, use hot water wash product, dry, with ethanol, boil to remove resinous impurities.Refilter, with ethanol wash elutant colourless till, dry, obtain micro-reddish yellow powder 15.6g, be 3-chlorine and connect ester mixture in indenes; After twice recrystallization of oil of mirbane, obtain faint yellow solid powder, 3-chlorine connects indenes lactone 3.8g, yield 6.3 ﹪.m.p.350～351℃。
Embodiment 3:
Thermometer is being housed, in reflux exchanger and churned mechanically four-hole bottle, is adding 3-chloro-phthalic anhydride 30.5g (0.167mol) and succinic acid (mol ratio is 1:2), be warming up to 210 ℃.Start stirring, add potassium acetate (0.05mol), 210 ℃ are reacted 2.5 hours.Then be cooled to 100 ℃, add hot water and import water vapour.Until reaction product forms broken particle, filter, use hot water wash product, dry, with ethanol, boil to remove resinous impurities.Refilter, with ethanol wash elutant colourless till, dry, obtain micro-reddish yellow powder 17.8g, be 3-chlorine and connect ester mixture in indenes; After twice recrystallization of oil of mirbane, obtain faint yellow solid powder, 3-chlorine connects indenes lactone 3.6g, yield 6.0 ﹪.m.p.350～351℃。
Reference
[1]Schobel?U,Egelhaaf?H?J,.Brechl?A.Bioconjugate?Chem.,1999,10(6):1107-1114
[2]Mujumbdar?S?R,Mujumbdar?R?B,Waggoner?C?M.Bioconjugate?Chem.,1996,7(3):356-362
[3] Li Ping, Li Dong. the synthetic and performance test of bi-indene isolactone. Institutes Of Technology Of Tianjin's journal, 2009,25(5): 19-21.

Claims (2)

1. fluorescence organic compound 3-chlorine connects an indenes lactone, and its structural formula is:
Figure FDA0000435212490000011
2. 3-chlorine claimed in claim 1 connects a synthetic method for indenes lactone, it is characterized in that comprising:
Synthetic route:
Figure FDA0000435212490000012
Concrete synthesis step is as follows:
Thermometer is being housed, in reflux exchanger and churned mechanically four-hole bottle, add 3-chloro-phthalic anhydride and succinic acid for the ratio of 1:1～2 in molar ratio, be warming up to 210 ℃, start stirring, add potassium acetate, the mol ratio of potassium acetate and 3-chloro-phthalic anhydride is 0.2～0.35:1, 210 ℃ are reacted 2～4 hours, then be cooled to 100 ℃, add hot water and import water vapour, until reaction product forms broken particle, filter, use hot water wash product, dry, with ethanol, boil to remove resinous impurities, refilter, with ethanol wash elutant colourless till, dry, obtain micro-reddish yellow powder, be 3-chlorine and connect ester mixture in indenes, after twice recrystallization of oil of mirbane, obtain faint yellow solid powder, 3-chlorine connects indenes lactone.
CN201310681241.2A 2013-12-11 2013-12-11 Fluorescent organic compound 3-chloroindene lactone and synthetic method thereof Pending CN103613570A (en)

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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101570526A (en) * 2008-05-30 2009-11-04 天津理工大学 Solid magnetism and fluorescence organic compound 4-methyl bi-indene isolactone and synthetic method
CN101570527A (en) * 2008-05-30 2009-11-04 天津理工大学 Solid magnetism and fluorescence organic compound 3-chlorin bi-indene isolactone and synthetic method
CN101591317A (en) * 2008-05-30 2009-12-02 天津理工大学 Solid magnetic and fluorescence organic compound 4-chlorin bi-indene isolactone and synthetic method

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101570526A (en) * 2008-05-30 2009-11-04 天津理工大学 Solid magnetism and fluorescence organic compound 4-methyl bi-indene isolactone and synthetic method
CN101570527A (en) * 2008-05-30 2009-11-04 天津理工大学 Solid magnetism and fluorescence organic compound 3-chlorin bi-indene isolactone and synthetic method
CN101591317A (en) * 2008-05-30 2009-12-02 天津理工大学 Solid magnetic and fluorescence organic compound 4-chlorin bi-indene isolactone and synthetic method

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
李平 等: "连茚异内酯的合成与性能测试", 《天津理工大学学报》 *

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Application publication date: 20140305