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有机硫化合物

有机硫化合物是指含有硫原子的有机化合物。这些化合物在自然界中广泛存在,在医药、农药和材料科学等领域有着重要的应用。有机硫化合物因其化学性质独特,在药物设计、合成化学以及材料制备方面扮演着重要角色。

1. 结构与分类

有机硫化合物可以按硫的连接方式分为饱和和不饱和类,如二硫化物、噻吩衍生物、砜等。常见的结构类型有:

  • 二硫化物:含-S-S-键的化合物。
  • 硫醚(Thiols):含有-R-S-H或-R-S-R 基团的化合物。
  • 磺酸酯(Sulfonates)与磺酸盐(Sulfonates):带有-SO3H基团的化合物,广泛应用于合成和制药领域。
  • 噻吩及其衍生物:具有环状结构的有机硫化物。
2. 生物学活性

许多有机硫化合物在生物学上有重要功能或应用潜力。例如:

  • 某些硫醚类药物被用于抗真菌、抗菌以及抗癌治疗。
  • 硫代葡萄糖苷(Glycosinolate)是十字花科植物中的一种天然存在物质,具有生物活性。
3. 合成方法

有机硫化合物可通过多种途径合成:

  • 亲核取代反应:使用含硫试剂与卤化物进行反应。
  • 自由基加成法:采用氧化剂引发自由基形成,通过烯烃与H2S、R-S-H等反应制备。
  • 金属催化转化:利用钯、铜等催化剂促进特定硫化过程。
4. 应用领域

有机硫化合物的应用广泛:

  • 医药领域:用于开发抗菌剂、抗病毒药物及抗癌药物等。
  • 农学研究:某些有机硫化合物作为生物农药的有效成分,能够抑制病害的发生。
  • 材料科学与技术:在导电聚合物和塑料添加剂中有重要应用。
5. 环境与安全性

尽管有机硫化合物具有许多潜在益处,但其生产和使用也可能对环境造成影响。因此,在设计和合成这些化合物时需要考虑可持续性和环保性因素。

以上是对有机硫化合物的简单介绍,包括它们的结构、生物学活性、合成方法及其应用领域等基本信息。

中文名称 英文名称 CAS号 化学式 结构式图片
—— dimethyl (3S,4S,6S)-5,5-dicyano-4-(4-fluorophenyl)-2-hydroxy-6-(4-methylsulfanylphenyl)cyclohexene-1,3-dicarboxylate —— C25H21FN2O5S
dimethyl (3S,4S,6S)-5,5-dicyano-4-(4-fluorophenyl)-2-hydroxy-6-(4-methylsulfanylphenyl)cyclohexene-1,3-dicarboxylate
—— dimethyl (3S,4R,6S)-5,5-dicyano-2-hydroxy-6-(4-methylsulfanylphenyl)-4-pyridin-4-ylcyclohexene-1,3-dicarboxylate —— C24H21N3O5S
dimethyl (3S,4R,6S)-5,5-dicyano-2-hydroxy-6-(4-methylsulfanylphenyl)-4-pyridin-4-ylcyclohexene-1,3-dicarboxylate
—— (8R,8aS)-6-amino-8-(4-methylsulfanylphenyl)-2-propyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile —— C22H23N5S
(8R,8aS)-6-amino-8-(4-methylsulfanylphenyl)-2-propyl-1,3,8,8a-tetrahydroisoquinoline-5,7,7-tricarbonitrile
—— (3S,4R)-1-benzyl-3,4-bis[(4-chlorophenyl)sulfanyl]pyrrolidine-2,5-dione —— C23H17Cl2NO2S2
(3S,4R)-1-benzyl-3,4-bis[(4-chlorophenyl)sulfanyl]pyrrolidine-2,5-dione
—— (3R)-3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]sulfanyloxolane-2,5-dione —— C10H5ClF3NO3S
(3R)-3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]sulfanyloxolane-2,5-dione
—— (3S)-3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]sulfanyloxolane-2,5-dione —— C10H5ClF3NO3S
(3S)-3-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]sulfanyloxolane-2,5-dione
—— (2Z,5R)-2-[(Z)-[(1R)-cyclohex-3-en-1-yl]methylidenehydrazinylidene]-5-[[4-(difluoromethylsulfanyl)phenyl]methyl]-1,3-thiazolidin-4-one —— C18H19F2N3OS2
(2Z,5R)-2-[(Z)-[(1R)-cyclohex-3-en-1-yl]methylidenehydrazinylidene]-5-[[4-(difluoromethylsulfanyl)phenyl]methyl]-1,3-thiazolidin-4-one
—— 2-[(2,5-dimethylphenyl)methylsulfanyl]-5-[(2S)-pyrrolidin-1-ium-2-yl]-1,3,4-oxadiazole —— C15H20N3OS+
2-[(2,5-dimethylphenyl)methylsulfanyl]-5-[(2S)-pyrrolidin-1-ium-2-yl]-1,3,4-oxadiazole
—— cyclohexyl 2-[[5-[(2,4-dimethylanilino)methyl]-4-[[(2S)-oxolan-2-yl]methyl]-1,2,4-triazol-3-yl]sulfanyl]acetate —— C24H34N4O3S
cyclohexyl 2-[[5-[(2,4-dimethylanilino)methyl]-4-[[(2S)-oxolan-2-yl]methyl]-1,2,4-triazol-3-yl]sulfanyl]acetate
—— 2-(3-Chlorobenzylthio)-5-(4-pyridyl)-1,3,4-oxadiazole —— C14H10ClN3OS
2-(3-Chlorobenzylthio)-5-(4-pyridyl)-1,3,4-oxadiazole
—— (1S,5S,6R)-2-amino-4,4-dimethoxy-6-(4-methylsulfanylphenyl)-3-azabicyclo[3.1.0]hex-2-ene-1,5-dicarbonitrile —— C16H16N4O2S
(1S,5S,6R)-2-amino-4,4-dimethoxy-6-(4-methylsulfanylphenyl)-3-azabicyclo[3.1.0]hex-2-ene-1,5-dicarbonitrile
—— (1S,5S,6S)-2-amino-4,4-dimethoxy-6-(4-methylsulfanylphenyl)-3-azabicyclo[3.1.0]hex-2-ene-1,5-dicarbonitrile —— C16H16N4O2S
(1S,5S,6S)-2-amino-4,4-dimethoxy-6-(4-methylsulfanylphenyl)-3-azabicyclo[3.1.0]hex-2-ene-1,5-dicarbonitrile
—— N-(2-Methoxy-ethyl)-4-[4-(6-phenylsulfanyl-imidazo[1,2-a]pyridin-3-yl)-pyrimidin-2-ylamino]-benzenesulfonamide —— C26H24N6O3S2
N-(2-Methoxy-ethyl)-4-[4-(6-phenylsulfanyl-imidazo[1,2-a]pyridin-3-yl)-pyrimidin-2-ylamino]-benzenesulfonamide
—— (4E)-4-{4-[(4-chlorophenyl)sulfanyl]benzylidene}-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one —— C23H17ClN2OS
(4E)-4-{4-[(4-chlorophenyl)sulfanyl]benzylidene}-5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one
—— ethyl (1S,5S,6R)-5-hydroxy-4,4-dimethyl-1-(trifluoromethyl)-2-oxa-7-thiabicyclo[3.2.1]octane-6-carboxylate —— C12H17F3O4S
ethyl (1S,5S,6R)-5-hydroxy-4,4-dimethyl-1-(trifluoromethyl)-2-oxa-7-thiabicyclo[3.2.1]octane-6-carboxylate
—— [(E)-4-amino-3-cyano-2-oxopent-3-enyl] 3-(2-chlorophenyl)sulfanylpropanoate —— C15H15ClN2O3S
[(E)-4-amino-3-cyano-2-oxopent-3-enyl] 3-(2-chlorophenyl)sulfanylpropanoate
—— ethyl (1S,5S,6S)-5-hydroxy-4,4-dimethyl-1-(trifluoromethyl)-2-oxa-7-thiabicyclo[3.2.1]octane-6-carboxylate —— C12H17F3O4S
ethyl (1S,5S,6S)-5-hydroxy-4,4-dimethyl-1-(trifluoromethyl)-2-oxa-7-thiabicyclo[3.2.1]octane-6-carboxylate
—— (14Z)-14-[[5-(1,3-benzothiazol-2-ylsulfanyl)furan-2-yl]methylidene]-11-phenyl-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one —— C32H21N3O2S3
(14Z)-14-[[5-(1,3-benzothiazol-2-ylsulfanyl)furan-2-yl]methylidene]-11-phenyl-15-thia-12,17-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(10),2,4,6,16-pentaen-13-one
—— (10Z)-10-({5-[(4-chlorophenyl)sulfanyl]furan-2-yl}methylidene)-7-(2-methoxyphenyl)-5,7-dihydro-6H-benzo[h][1,3]thiazolo[2,3-b]quinazolin-9(10H)-one —— C32H23ClN2O3S2
(10Z)-10-({5-[(4-chlorophenyl)sulfanyl]furan-2-yl}methylidene)-7-(2-methoxyphenyl)-5,7-dihydro-6H-benzo[h][1,3]thiazolo[2,3-b]quinazolin-9(10H)-one
—— (2S)-2-hydroxy-2-(2-methylsulfanylpyrimidin-4-yl)acetonitrile —— C7H7N3OS
(2S)-2-hydroxy-2-(2-methylsulfanylpyrimidin-4-yl)acetonitrile
—— (2R)-2-hydroxy-2-(2-methylsulfanylpyrimidin-4-yl)acetonitrile —— C7H7N3OS
(2R)-2-hydroxy-2-(2-methylsulfanylpyrimidin-4-yl)acetonitrile
—— [(2R)-1-(tert-butylamino)-1-oxopropan-2-yl] (1'S,5'S)-spiro[1,3-dithiolane-2,9'-bicyclo[3.3.1]nonane]-3'-carboxylate —— C19H31NO3S2
[(2R)-1-(tert-butylamino)-1-oxopropan-2-yl] (1'S,5'S)-spiro[1,3-dithiolane-2,9'-bicyclo[3.3.1]nonane]-3'-carboxylate
—— (5R,7R)-3-(3-nitro-1,2,4-triazol-1-yl)-N-(2-phenylsulfanylphenyl)adamantane-1-carboxamide —— C25H25N5O3S
(5R,7R)-3-(3-nitro-1,2,4-triazol-1-yl)-N-(2-phenylsulfanylphenyl)adamantane-1-carboxamide
—— (5S,7S)-3-(3-nitro-1,2,4-triazol-1-yl)-N-(2-phenylsulfanylphenyl)adamantane-1-carboxamide —— C25H25N5O3S
(5S,7S)-3-(3-nitro-1,2,4-triazol-1-yl)-N-(2-phenylsulfanylphenyl)adamantane-1-carboxamide
—— [(2S)-1-(tert-butylamino)-1-oxopropan-2-yl] (1'S,5'S)-spiro[1,3-dithiolane-2,9'-bicyclo[3.3.1]nonane]-3'-carboxylate —— C19H31NO3S2
[(2S)-1-(tert-butylamino)-1-oxopropan-2-yl] (1'S,5'S)-spiro[1,3-dithiolane-2,9'-bicyclo[3.3.1]nonane]-3'-carboxylate
—— (6Z)-2-butyl-6-[[5-(4-chlorophenyl)sulfanylfuran-2-yl]methylidene]-5-imino-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-one —— C20H17ClN4O2S2
(6Z)-2-butyl-6-[[5-(4-chlorophenyl)sulfanylfuran-2-yl]methylidene]-5-imino-[1,3,4]thiadiazolo[3,2-a]pyrimidin-7-one
—— (1R,4S)-4,7,7-trimethyl-2,3-dioxo-N-(2-phenylsulfanylphenyl)bicyclo[2.2.1]heptane-1-carboxamide —— C23H23NO3S
(1R,4S)-4,7,7-trimethyl-2,3-dioxo-N-(2-phenylsulfanylphenyl)bicyclo[2.2.1]heptane-1-carboxamide
—— 3-(2-Chlorobenzyl)-5-({5-[(4-chlorophenyl)sulfanyl]thien-2-yl}methylene)-1,3-thiazolidine-2,4-dione —— C21H13Cl2NO2S3
3-(2-Chlorobenzyl)-5-({5-[(4-chlorophenyl)sulfanyl]thien-2-yl}methylene)-1,3-thiazolidine-2,4-dione
—— (1'R,5'R)-N-(furan-2-ylmethyl)spiro[1,3-dithiolane-2,9'-bicyclo[3.3.1]nonane]-3'-carboxamide —— C17H23NO2S2
(1'R,5'R)-N-(furan-2-ylmethyl)spiro[1,3-dithiolane-2,9'-bicyclo[3.3.1]nonane]-3'-carboxamide
—— (1'S,5'S)-N-(furan-2-ylmethyl)spiro[1,3-dithiolane-2,9'-bicyclo[3.3.1]nonane]-3'-carboxamide —— C17H23NO2S2
(1'S,5'S)-N-(furan-2-ylmethyl)spiro[1,3-dithiolane-2,9'-bicyclo[3.3.1]nonane]-3'-carboxamide
—— prop-2-enyl (2E,5S)-2-[[5-(3-chlorophenyl)furan-2-yl]methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C29H23ClN2O4S2
prop-2-enyl (2E,5S)-2-[[5-(3-chlorophenyl)furan-2-yl]methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— (5Z)-3-(2-chloro-6-fluorobenzyl)-5-({5-[(4-chlorophenyl)sulfanyl]thiophen-2-yl}methylidene)-1,3-thiazolidine-2,4-dione —— C21H12Cl2FNO2S3
(5Z)-3-(2-chloro-6-fluorobenzyl)-5-({5-[(4-chlorophenyl)sulfanyl]thiophen-2-yl}methylidene)-1,3-thiazolidine-2,4-dione
—— methyl (2E,5R)-2-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H21ClN2O4S2
methyl (2E,5R)-2-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— methyl (2E,5S)-2-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate —— C27H21ClN2O4S2
methyl (2E,5S)-2-[[5-(2-chlorophenyl)furan-2-yl]methylidene]-7-methyl-5-(4-methylsulfanylphenyl)-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
—— 1-[(3R)-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3S)-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea —— C22H26N4O4S5
1-[(3R)-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3S)-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea
—— 2-[(5-benzylsulfanyl-1,3,4-thiadiazol-2-yl)sulfanyl]-N-[(Z)-[(E)-2-chloro-3-phenylprop-2-enylidene]amino]acetamide —— C20H17ClN4OS3
2-[(5-benzylsulfanyl-1,3,4-thiadiazol-2-yl)sulfanyl]-N-[(Z)-[(E)-2-chloro-3-phenylprop-2-enylidene]amino]acetamide
—— 1-[(3R)-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3R)-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea —— C22H26N4O4S5
1-[(3R)-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3R)-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea
—— 1-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3S)-3-methyl-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea —— C24H30N4O4S5
1-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3S)-3-methyl-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea
—— 1-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3R)-3-methyl-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea —— C24H30N4O4S5
1-[(3R)-3-methyl-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3R)-3-methyl-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea
—— 1-[(3S)-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3S)-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea —— C22H26N4O4S5
1-[(3S)-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3S)-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea
—— 1-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3R)-3-methyl-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea —— C24H30N4O4S5
1-[(3S)-3-methyl-1,1-dioxothiolan-3-yl]-3-[4-[4-[[(3R)-3-methyl-1,1-dioxothiolan-3-yl]carbamothioylamino]phenyl]sulfanylphenyl]thiourea
—— 2-[[5-[(4-chlorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]sulfanyl]-N-[(Z)-[(Z)-3-(furan-2-yl)prop-2-enylidene]amino]acetamide —— C18H15ClN4O2S3
2-[[5-[(4-chlorophenyl)methylsulfanyl]-1,3,4-thiadiazol-2-yl]sulfanyl]-N-[(Z)-[(Z)-3-(furan-2-yl)prop-2-enylidene]amino]acetamide
—— 2-[(2-bromophenyl)methylsulfanyl]-4H-[1,3]thiazolo[4,5-d]pyrimidine-5,7-dione —— C12H8BrN3O2S2
2-[(2-bromophenyl)methylsulfanyl]-4H-[1,3]thiazolo[4,5-d]pyrimidine-5,7-dione
—— N-cyclohexyl-2-[(4-methoxy-6-oxo-1,6-dihydropyrimidin-2-yl)sulfanyl]propanamide —— C14H21N3O3S
N-cyclohexyl-2-[(4-methoxy-6-oxo-1,6-dihydropyrimidin-2-yl)sulfanyl]propanamide
—— 2-[[5,6-Bis(furan-3-yl)-1,2,4-triazin-3-yl]sulfanyl]-1-(5-chlorothiophen-2-yl)ethanone —— C17H10ClN3O3S2
2-[[5,6-Bis(furan-3-yl)-1,2,4-triazin-3-yl]sulfanyl]-1-(5-chlorothiophen-2-yl)ethanone
—— 2-{[3-cyano-4-(methoxymethyl)-6-methylpyridin-2-yl]sulfanyl}-N-(1-methoxypropan-2-yl)acetamide —— C15H21N3O3S
2-{[3-cyano-4-(methoxymethyl)-6-methylpyridin-2-yl]sulfanyl}-N-(1-methoxypropan-2-yl)acetamide
—— 2-[(4-methylphenyl)methylsulfanyl]-4H-[1,3]thiazolo[4,5-d]pyrimidine-5,7-dione —— C13H11N3O2S2
2-[(4-methylphenyl)methylsulfanyl]-4H-[1,3]thiazolo[4,5-d]pyrimidine-5,7-dione
—— 7-amino-2-ethyl-9H-[1,2,4]triazolo[5,1-b][1,3]benzothiazin-9-ol —— C11H12N4OS
7-amino-2-ethyl-9H-[1,2,4]triazolo[5,1-b][1,3]benzothiazin-9-ol
—— 3-[(5-Amino-1,2,4-thiadiazol-3-yl)sulfanyl]propanenitrile —— C5H6N4S2
3-[(5-Amino-1,2,4-thiadiazol-3-yl)sulfanyl]propanenitrile
—— 2-{[5-(4-amino-1,2,5-oxadiazol-3-yl)-4-ethyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N-cyclopentylacetamide —— C13H19N7O2S
2-{[5-(4-amino-1,2,5-oxadiazol-3-yl)-4-ethyl-4H-1,2,4-triazol-3-yl]sulfanyl}-N-cyclopentylacetamide