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1,2 - the imidazoline reduction reaction 2 fluorescent probe dye rhodamine carbon intermediates synthesized research

Author: GuanLi
Tutor: ShiZhen;WangYunXia
School: Northwestern University
Course: Organic Chemistry
Keywords: 2 - imidazoline Sodium borohydride Reduction Ethylenediamine derivatives Carbon rhodamine intermediates
CLC: O621.25
Type: Master's thesis
Year: 2011
Downloads: 69
Quote: 0
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Abstract


The papers include 2 - the imidazoline reduction reaction and the fluorescent probe dyes carbon rhodamine intermediates synthesis of two parts. The first part of this paper is the reduction reaction of 2 - imidazoline. As an important five-membered heterocyclic compounds, 2 - imidazoline attract pharmaceutical chemistry, chemists in the field of organic synthetic chemistry, natural product chemistry, coordination chemistry and homogeneous catalysis concern. Synthesis of imidazoline continuously improved in the past two years, in order to meet the needs of diverse structure. Imidazoline synthesis methods have been approaching perfect, but a reduction reaction of the imidazoline little research. At present, only our group 2 - imidazoline in NaBH4/HCl under the conditions of the reduction reaction of a preliminary study. This thesis is based on System 2 - imidazoline reduction reaction of NaBH4 system. Papers prepared six typical 2 - imidazoline, and a comprehensive study of these six 2 - the imidazoline NaBH4/I2 system the, NaBH4/CoCl2 system the, NaBH4/AlCl3 system the, NaBH4/ZnCl2 system, NaBH4/CeCl3 system reduction reaction NaBH4/TiCl4 system under the structure of the product by means of the infrared flight mass spectrometry, GC and proton nuclear magnetic resonance spectrum characterized by different reduction system for the reduction reaction, the same reduction system 2 - substituent the different reduction reaction, and discuss the mechanism of reduction. The results show that the 2 - imidazolin-in six reduction system, the ring-opening reaction, generating a series of asymmetrically substituted derivatives of ethylenediamine, wherein NaBH4/I2 reducing effect of the system is preferably. Detailed study of this thesis - imidazoline NaBH4 system reduction reaction at the same time, also an important organic synthesis of a new method for asymmetrically substituted ethylenediamine derivatives, the work of Organic Chemistry of the basic theory and applications the development of the study have an important role. The second part of this paper is a synthesis of fluorescent probe dye carbon rhodamine intermediates. The design and synthesis of organic fluorescent dyes and their biological applied research is a hot topic in the study of organic chemistry and biology. The long wavelength fluorescent probe dye because it can effectively avoid vivo background fluorescence interference, and has good penetrating tissue and other acclaimed. Carbon the rhodamine class of compounds fluorescence quantum yield and fluorescence spectral redshift magnitude larger, and therefore is a class of very promising performance fluorescent probe dyes. About carbon rhodamine derivatives synthesis rarely reported in the literature. The paper intends to design synthesis of a new class of organic carbon rhodamine fluorescence dye. Experimental Design first synthesis of N, N-dibenzyl-amino-3 - isopropenyl aniline (I) and 2 - (4-N, N-two benzyl amino-benzoyl) benzoic acid (II) the two important intermediates , followed by two intermediate condensation under acidic conditions to form the target compound. Paper work to the amino acid and aniline as raw material, alcoholization and dehydration reaction intermediate (I) was synthesized by esterification, amino protection, and analysis of the intermediate (I) were characterized by means of IR, GC-MS, and other test. Synthetic intermediates (II) study is ongoing. The research work on the synthesis and biological applications of behind carbon rhodamine fluorescence probe dye has important reference value.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Organic Chemistry general issues > Properties of organic compounds > Chemical properties of organic reactions
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