芳二炔甲硫醚类化合物的一锅合成研究
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摘要
末端含有多个硫甲基功能基的有机分子可将纳米粒子组装成尺度或形态可调节的纳米团簇。本实验室过去已经设计并合成了形态多样、具有π共轭体系的多硫甲基功能基芳炔硫醚类分子。这对获得一些具有良好组装效果尤其是能够控制团簇形态或控制团簇尺度的功能分子有着重要的意义。在这些工作的基础上,本文合成了一些形态相异、具有π共轭体系的多硫甲基功能基芳二炔甲硫醚类化合物。
卤代芳二炔甲硫醚类化合物是构筑上述多硫甲基功能基芳二炔甲硫醚类化合物的重要原料。但目前尚无好的方法制备这类化合物。为此,本文对利用亲核硫试剂甲硫基甲基苯基砜(MP-S)与芳基丙炔醛合成芳二炔甲硫醚类化合物的方法学进行了考察。本文先以改进后的Ogura法合成了MP-S;以卤代芳烃为起始物,经过Sonogashira反应和氧化反应合成了一系列芳基丙炔醛。之后,本文探讨了MP-S和芳基丙炔醛的一锅合成法,并成功得合成了一系列芳二炔甲硫醚类化合物。该法具有原料易得、合成简便、产率较高等优点。
为了探明芳二炔甲硫醚类化合物的形成机制,本文分阶段对该反应的机理进行了探讨。通过对反应中各阶段生成的中间体的捕捉及结构分析,对反应过程进行了确认,最终证实了双消除反应机理的设想。X射线单晶衍射实验结果表明,双键中间体的构型为E式构型。
本文最后利用一锅法制得的卤代芳二炔甲硫醚考察了V型和Y型两种多硫甲基功能基芳二炔甲硫醚类化合物的合成。碘代芳二炔甲硫醚类化合物分别与间二苯乙炔和均三苯乙炔通过Sonogashira反应成功地合成了V型和Y型两种多硫甲基功能基芳二炔甲硫醚类化合物。
本文中部分中间体和所有目标化合物的结构均通过~1H NMR、~(13)C NMR、MS和IR组合测定得到确认。
Organic compounds, that contain several thiomethyls at the terminal, can assemble nanoparticles to nanoparticle clusters, whose size and shape can be adjusted by the compounds. Our laboratory had designed and synthesized arylethyne thio ethers, which are different in shape,πconjugated and contain several thiomethyls. Those compounds are important for getting some functional molecules that have good assembling effect, especially for getting those that can control the shape and the size of the cluster. Based on the preceding research of our laboratory, this paper synthesized some aryldiynes thio ethers,which areπconjugated and contain several thiomethyls at the terminal.
Halogenated aryldiynes methylthio ethers are important material for synthesizing aryldiynes methylthio ethers that have several thiomethyls at the terminal. But there haven’t been any satisfactory methods for preparing those compounds so far. Therefore, this paper studied the methodology for preparation of aryldiynes methylthio ethers using methyl thio methyl phenyl sulfone (MP-S) and arylpropargyl aldehydes. Firstly, MP-S was prepared according to the modified Ogura method, and a series of arylpropargyl aldehydes were synthesized from halogenated arenes by Sonogashira reaction and oxidation. Then, the one-pot reaction using MP-S and arylpropargyl aldehydes was discussed, and a series of aryldiynes methylthio ethers were successfully prepared accordingly. The method has following advantages: accessible materials, simple manipulation and good yield.
In order to clarify the course of the formation of aryldiynes methylthio ethers, the mechanism of the one pot reaction was studied step by step. After trapping and structure analysis of the intermediates forming at the different steps of the reaction, the mechanism of double elimination was confirmed. The results from X-ray crystallographic analysis indicated that the intermediates with double bond have E configuration.
In the last part of the paper, the preparation of V shaped and Y shaped aryldiynes methylthio ethers with several thiomethyls at the terminal were studied using halogenated aryldiynes methylthio ethers synthesized by one-pot reaction. Iodic aryldiynes methylthio ethers reacted with diarylethyne and triarylethyne respectly by Sonogashira reaction afforded successfully V shaped and Y shaped aryldiynes methylthio ethers.
The structure of some intermediates and all target compounds synthesized in this paper were characterized by ~1H NMR, ~(13)C NMR, MS and IR.
卤代芳二炔甲硫醚类化合物是构筑上述多硫甲基功能基芳二炔甲硫醚类化合物的重要原料。但目前尚无好的方法制备这类化合物。为此,本文对利用亲核硫试剂甲硫基甲基苯基砜(MP-S)与芳基丙炔醛合成芳二炔甲硫醚类化合物的方法学进行了考察。本文先以改进后的Ogura法合成了MP-S;以卤代芳烃为起始物,经过Sonogashira反应和氧化反应合成了一系列芳基丙炔醛。之后,本文探讨了MP-S和芳基丙炔醛的一锅合成法,并成功得合成了一系列芳二炔甲硫醚类化合物。该法具有原料易得、合成简便、产率较高等优点。
为了探明芳二炔甲硫醚类化合物的形成机制,本文分阶段对该反应的机理进行了探讨。通过对反应中各阶段生成的中间体的捕捉及结构分析,对反应过程进行了确认,最终证实了双消除反应机理的设想。X射线单晶衍射实验结果表明,双键中间体的构型为E式构型。
本文最后利用一锅法制得的卤代芳二炔甲硫醚考察了V型和Y型两种多硫甲基功能基芳二炔甲硫醚类化合物的合成。碘代芳二炔甲硫醚类化合物分别与间二苯乙炔和均三苯乙炔通过Sonogashira反应成功地合成了V型和Y型两种多硫甲基功能基芳二炔甲硫醚类化合物。
本文中部分中间体和所有目标化合物的结构均通过~1H NMR、~(13)C NMR、MS和IR组合测定得到确认。
Organic compounds, that contain several thiomethyls at the terminal, can assemble nanoparticles to nanoparticle clusters, whose size and shape can be adjusted by the compounds. Our laboratory had designed and synthesized arylethyne thio ethers, which are different in shape,πconjugated and contain several thiomethyls. Those compounds are important for getting some functional molecules that have good assembling effect, especially for getting those that can control the shape and the size of the cluster. Based on the preceding research of our laboratory, this paper synthesized some aryldiynes thio ethers,which areπconjugated and contain several thiomethyls at the terminal.
Halogenated aryldiynes methylthio ethers are important material for synthesizing aryldiynes methylthio ethers that have several thiomethyls at the terminal. But there haven’t been any satisfactory methods for preparing those compounds so far. Therefore, this paper studied the methodology for preparation of aryldiynes methylthio ethers using methyl thio methyl phenyl sulfone (MP-S) and arylpropargyl aldehydes. Firstly, MP-S was prepared according to the modified Ogura method, and a series of arylpropargyl aldehydes were synthesized from halogenated arenes by Sonogashira reaction and oxidation. Then, the one-pot reaction using MP-S and arylpropargyl aldehydes was discussed, and a series of aryldiynes methylthio ethers were successfully prepared accordingly. The method has following advantages: accessible materials, simple manipulation and good yield.
In order to clarify the course of the formation of aryldiynes methylthio ethers, the mechanism of the one pot reaction was studied step by step. After trapping and structure analysis of the intermediates forming at the different steps of the reaction, the mechanism of double elimination was confirmed. The results from X-ray crystallographic analysis indicated that the intermediates with double bond have E configuration.
In the last part of the paper, the preparation of V shaped and Y shaped aryldiynes methylthio ethers with several thiomethyls at the terminal were studied using halogenated aryldiynes methylthio ethers synthesized by one-pot reaction. Iodic aryldiynes methylthio ethers reacted with diarylethyne and triarylethyne respectly by Sonogashira reaction afforded successfully V shaped and Y shaped aryldiynes methylthio ethers.
The structure of some intermediates and all target compounds synthesized in this paper were characterized by ~1H NMR, ~(13)C NMR, MS and IR.
引文
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[2] Braga A L, Comasseto J V, Petragnani N. Pyrolysis ofα-thio phosporanes→thioacetylenes. Tetrahedron Lett., 1984, 25(11): 1111~1114
[3] Voets M, Smet M, Dehaen W. Ruthenium-catalyzed [2+2] cycloaddition of alkynyl sulfides and alkynyl sulfones. J. Chem. Soc., Perkin Trans. 1, 1999, 1473~1475
[4]安德烈,孟桂英,张志扬等.双消除法一锅合成甲硫芳炔化合物.化学学报, 2006, 64(21): 2190~2196
[5]桑晓燕,王冬,蔡明中.炔基硫醚的制备和(E)-α-碘代烯基硫醚的立体选择性合成.江西师范大学学报(自然科学版), 2006, 30(3): 205~208
[6] Maruyama H, Hiraoka T. A stereocontrolled synthesis of thienamycin from 6-aminopenicillanic acid. J. Org. Chem., 1986, 51(3): 399~402
[7] Magriotis P A, Kim K D. Ireland-claisen rearrangements of enediyne lactones: tandem claisen-bergman strategy for stereocontrolled tetrahydronaphthalene synthesis. J. Am. Chem. Soc., 1993, 115(7): 2972~2973
[8] Braga A L, Reckziegel A, Menezes P H, et al. Alkynyl sulfides and selenides from alkynyl bromides and diorganoyl chalcogenides promoted by copper(I) iodide. Tetrahedron Lett., 1993, 34(3): 393
[9] Braga A L, Silveira C C, Reckziegel A, et al. Convenient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes and phenylchalcogenyl halides in the presence of copper(I) iodide. Tetrahedron Lett., 1993, 34(50): 8041
[10] Lothar W B, Margarete F S, Paulo H M. Short and efficient preparation of alkynyl selenides, sulfides and tellurides from terminal alkynes. Tetrahedron Lett., 2004, 45(13): 2735~2737
[11] Braga A L, Martins T L C, Silveira C C, et al. Synthesis of chalcogenol esters from chalcogenoacetylenes. Tetrahedron, 2001, 57(16): 3297~3300
[12] Riddell N, Tam W. Ruthenium-catalyzed [2+2] cycloadditions of alkynyl sulfides and alkynyl sulfones. J. Org. Chem., 2006, 71(5): 1934~1937
[13] Gerhard H, Steffen L, Klaus H. The First broad application of alkynyl sulfides as dienophiles in cobalt(I)-catalyzed Diels-Alder reactions. J. Org. Chem., 2004, 69(3): 624~630
[14] Savarin C, Srogl J, Liebeskind L S. Substituted alkyne synthesis under nonbasicconditions: copper carboxylate-mediated, palladium-catalyzed thioalkyneboronic acid cross-coupling. Org. Lett., 2001, 3(1): 91~93
[15] Han L, Daniel D R, Maye M M, et al. Core-shell nanostructured nanoparticle films as chemically sensitive interfaces. Anal. Chem., 2001, 73(18): 4441~4449
[16] Zhong C-J, Maye M M. Core-shell assembled nanoparticles as catalysts. Adv. Mater., 2001, 13(19): 1507~1511
[17] Elghanian R, Storhoff J J, Mucic R C, et al. Selective colorimetric detection of polynucleotides based on the distance-dependent optical properties of gold nanoparticles. Science, 1997, 277(5329): 1078~1081
[18] Lim I-I S, Ip W, Crew E, et al. Homocysteine-mediated reactivity and assembly of gold nanoparticles. Langmuir, 2007, 23(2): 826~833
[19] Frankamp B L, Boal A K, Rotello V M. Controlled interparticle spacing through self-assembly of Au nanoparticles and poly(amidoamine) dendrimers. J. Am. Chem. Soc., 2002, 124(51): 15146~15147
[20] Zubarev E R, Xu J, Sayyad A, et al. Amphiphilicity-driven organization of nanoparticles into discrete assemblies. J. Am. Chem. Soc., 2006, 128(47): 15098~15099
[21] Lim I-I S, Maye M M, Luo J, et al. Kinetic and thermodynamic assessments of the mediator-template assembly of nanoparticles. J. Phy. Chem. B, 2005, 109 (7): 2578~2583
[22] Hostetler M J, Templeton A C, Murray R W. Dynamics of place-exchange reactions on monolayer-protected gold cluster molecules. Langmuir, 1999, 15(11): 3782~3789
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