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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
—— methyl 4-methyl-5-phenylsulfanyl-(E,4S)-2-pentenoate 688364-58-1 C13H16O2S
methyl 4-methyl-5-phenylsulfanyl-(E,4S)-2-pentenoate
—— (4S,6S,8S,10S,14R,16R,18R,22R)-4,6,8,14,16,18,22-heptamethoxy-10-hydroxy-12-(trimethylenedithio)-1-pentacosene 160382-08-1 C35H68O8S2
(4S,6S,8S,10S,14R,16R,18R,22R)-4,6,8,14,16,18,22-heptamethoxy-10-hydroxy-12-(trimethylenedithio)-1-pentacosene
—— (3R,5R)-3-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-9-trimethylsilylnon-8-ynyl]-5-methyl-3-phenylsulfanyloxolan-2-one 152037-54-2 C29H48O3SSi2
(3R,5R)-3-[(2S)-2-[tert-butyl(dimethyl)silyl]oxy-9-trimethylsilylnon-8-ynyl]-5-methyl-3-phenylsulfanyloxolan-2-one
—— (4S,5R)-4-(fluoromethyl)-5-[4-(methylthio)phenyl]-2-phenyl-4,5-dihydro-1,3-oxazole 126428-98-6 C17H16FNOS
(4S,5R)-4-(fluoromethyl)-5-[4-(methylthio)phenyl]-2-phenyl-4,5-dihydro-1,3-oxazole
—— (S)-3-((R)-1-Hydroxymethyl-allyl)-6,10-dithia-spiro[4.5]decan-1-one 164229-10-1 C12H18O2S2
(S)-3-((R)-1-Hydroxymethyl-allyl)-6,10-dithia-spiro[4.5]decan-1-one
—— 1-((1R,2S)-2-Methyl-1-oxo-1λ<sup>4</sup>-[1,3]dithian-2-yl)-3-phenyl-propan-1-one 186146-40-7 C14H18O2S2
1-((1R,2S)-2-Methyl-1-oxo-1λ<sup>4</sup>-[1,3]dithian-2-yl)-3-phenyl-propan-1-one
—— 2-ethoxycarbonyl-2-phenylthio-3-vinylidene-5-pentanolide 144511-97-7 C16H16O4S
2-ethoxycarbonyl-2-phenylthio-3-vinylidene-5-pentanolide
—— 6,6-dimethyl-3-methylthio-1-(pyrid-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one 252056-21-6 C16H17NOS2
6,6-dimethyl-3-methylthio-1-(pyrid-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one
—— tert-Butyl-[(1S,3S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-4-(2-methyl-[1,3]dithian-2-yl)-butoxy]-dimethyl-silane 218439-21-5 C21H42O3S2Si
tert-Butyl-[(1S,3S)-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-methyl-4-(2-methyl-[1,3]dithian-2-yl)-butoxy]-dimethyl-silane
—— ethyl (4R,5S)-2,2-dimethyl-5-(2-methyl-1-phenylsulfanylpropan-2-yl)-1,3-dioxolane-4-carboxylate 169899-78-9 C18H26O4S
ethyl (4R,5S)-2,2-dimethyl-5-(2-methyl-1-phenylsulfanylpropan-2-yl)-1,3-dioxolane-4-carboxylate
—— (3'R,4''S)-methyl 2-[3'-(2"-dimethyl-1",3"-dioxolan-4"-yl)-3'-(2"'-furyl)]propyl-4-phenylthio-acetoacetate 256343-63-2 C23H28O6S
(3'R,4''S)-methyl 2-[3'-(2"-dimethyl-1",3"-dioxolan-4"-yl)-3'-(2"'-furyl)]propyl-4-phenylthio-acetoacetate
—— 1-{2,6-dichloro-4-[(phenylthio)methyl]pyridin-3-yl}hex-5-en-1-one 607708-24-7 C18H17Cl2NOS
1-{2,6-dichloro-4-[(phenylthio)methyl]pyridin-3-yl}hex-5-en-1-one
—— 2-((R)-4-Azido-nonyl)-2-((E)-(S)-4-methoxymethoxy-non-5-enyl)-[1,3]dithiane 211678-50-1 C24H45N3O2S2
2-((R)-4-Azido-nonyl)-2-((E)-(S)-4-methoxymethoxy-non-5-enyl)-[1,3]dithiane
—— 4-chloro-6-(N-isobutyloamino)-2-methylmercaptopyrimidine 841260-72-8 C9H14ClN3S
4-chloro-6-(N-isobutyloamino)-2-methylmercaptopyrimidine
—— 2-Methoxy-[1,3]dithiolo[4,5-d][1,3]dithiol-5-one 172949-09-6 C5H4O2S4
2-Methoxy-[1,3]dithiolo[4,5-d][1,3]dithiol-5-one
—— 3-(2,5-dimethylphenyl)-sulfanyl-propionic acid methyl ester 571167-32-3 C12H16O2S
3-(2,5-dimethylphenyl)-sulfanyl-propionic acid methyl ester
—— D-(-)-threo-2-phenyl-4-(4-(methylthio)phenyl)-2-oxazole-5-methanol 96795-24-3 C17H17NO2S
D-(-)-threo-2-phenyl-4-(4-(methylthio)phenyl)-2-oxazole-5-methanol
—— n-Hexadecyl-methyl-dithiolcarbonat 41320-32-5 C18H36OS2
n-Hexadecyl-methyl-dithiolcarbonat
—— (2-Methoxymethoxy-ethylsulfanyl)-benzene 123299-87-6 C10H14O2S
(2-Methoxymethoxy-ethylsulfanyl)-benzene
—— 3-(6,7-Dihydro-5H-thieno[3,2-b]thiopyran-3-yloxy)-propane-1,2-diol 177974-79-7 C10H14O3S2
3-(6,7-Dihydro-5H-thieno[3,2-b]thiopyran-3-yloxy)-propane-1,2-diol
—— (3S,4S)-5,5,5-trifluoro-4-hydroxy-3-(p-tolylthio)pentanoic acid 473435-94-8 C12H13F3O3S
(3S,4S)-5,5,5-trifluoro-4-hydroxy-3-(p-tolylthio)pentanoic acid
—— (3aR,6aR)-3-[1-((2R,3R,4S)-4-Methyl-5-oxo-3-phenylsulfanyl-tetrahydro-furan-2-yloxy)-meth-(E)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one 159655-80-8 C19H18O5S
(3aR,6aR)-3-[1-((2R,3R,4S)-4-Methyl-5-oxo-3-phenylsulfanyl-tetrahydro-furan-2-yloxy)-meth-(E)-ylidene]-3,3a,4,6a-tetrahydro-cyclopenta[b]furan-2-one
—— 4,5-Ethylenedithio-1,2-dithiol-3-thione 103656-48-0 C5H4S5
4,5-Ethylenedithio-1,2-dithiol-3-thione
—— tert-Butyl-((7R,9S)-9-methyl-8-oxa-1,4-dithia-spiro[4.5]dec-7-yloxy)-diphenyl-silane 148066-65-3 C24H32O2S2Si
tert-Butyl-((7R,9S)-9-methyl-8-oxa-1,4-dithia-spiro[4.5]dec-7-yloxy)-diphenyl-silane
—— [(E)-2-but-3-en-2-yloxy-3,3,3-trifluoroprop-1-enyl]sulfanylbenzene 177272-45-6 C13H13F3OS
[(E)-2-but-3-en-2-yloxy-3,3,3-trifluoroprop-1-enyl]sulfanylbenzene
—— [(E)-heptadec-2-enyl]sulfanylbenzene 172703-30-9 C23H38S
[(E)-heptadec-2-enyl]sulfanylbenzene
—— (2S)-2-[(2R)-1-[2-(2-methylpropyl)-1,3-dioxolan-2-yl]propan-2-yl]-6,10-dithiaspiro[4.5]decan-4-one 172332-72-8 C18H30O3S2
(2S)-2-[(2R)-1-[2-(2-methylpropyl)-1,3-dioxolan-2-yl]propan-2-yl]-6,10-dithiaspiro[4.5]decan-4-one
—— (S)-2,6-Dimethyl-3-phenylsulfanyl-hept-5-en-2-ol 143359-40-4 C15H22OS
(S)-2,6-Dimethyl-3-phenylsulfanyl-hept-5-en-2-ol
—— 5-Ethylsulfanyl-3-(2-methylpropyl)-1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione 199444-52-5 C16H30N2O3SSi
5-Ethylsulfanyl-3-(2-methylpropyl)-1-(2-trimethylsilylethoxymethyl)pyrimidine-2,4-dione
—— 4-bromo-5-(4-methoxybenzyl)-1-methyl-2-phenylsulfanyl-1H-imidazole 443095-82-7 C18H17BrN2OS
4-bromo-5-(4-methoxybenzyl)-1-methyl-2-phenylsulfanyl-1H-imidazole
—— O-propan-2-yl 4-hydroxybut-2-ynylsulfanylmethanethioate 205323-76-8 C8H12O2S2
O-propan-2-yl 4-hydroxybut-2-ynylsulfanylmethanethioate
—— 4-Pentene-2,3-diol, 1-[(2-aminophenyl)thio]-, [S-(R*,R*)]- 152009-53-5 C11H15NO2S
4-Pentene-2,3-diol, 1-[(2-aminophenyl)thio]-, [S-(R*,R*)]-
—— lithium;(Z)-methyl-(methylsulfanylmethylidene)-oxido-lambda4-sulfane —— C3H7LiOS2
lithium;(Z)-methyl-(methylsulfanylmethylidene)-oxido-lambda4-sulfane
—— but-3-enoic acid N-methyl-N-(5-(methylsulfanyl)furan-2-yl)amide 404575-52-6 C10H13NO2S
but-3-enoic acid N-methyl-N-(5-(methylsulfanyl)furan-2-yl)amide
—— 1-Mercapto-2-methylmercapto-maleonitril 88096-52-0 C5H4N2S2
1-Mercapto-2-methylmercapto-maleonitril
—— 5-(4-methoxybenzyl)-1-methyl-2-phenylsulfanyl-1H-imidazole 443095-81-6 C18H18N2OS
5-(4-methoxybenzyl)-1-methyl-2-phenylsulfanyl-1H-imidazole
—— (Z)-2-ethoxy-7-(furan-2-yl)-1-phenylsulfanylhept-1-en-3-ol 174907-91-6 C19H24O3S
(Z)-2-ethoxy-7-(furan-2-yl)-1-phenylsulfanylhept-1-en-3-ol
—— N-[(2-bromophenyl)methyl]-2-chloro-2-methylsulfanyl-N-(2-phenylsulfanylcyclohexen-1-yl)acetamide 205446-82-8 C22H23BrClNOS2
N-[(2-bromophenyl)methyl]-2-chloro-2-methylsulfanyl-N-(2-phenylsulfanylcyclohexen-1-yl)acetamide
—— 3,5-Bis-methylsulfanyl-[1,2,4]triazine-6-carboxylic acid 186959-29-5 C6H7N3O2S2
3,5-Bis-methylsulfanyl-[1,2,4]triazine-6-carboxylic acid
—— tris(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d ]bis[1,3]-dithiol-4-yl)methane 1416175-80-8 C46H52O6S12
tris(8-ethoxycarbonyl-2,2,6,6-tetramethylbenzo[1,2-d;4,5-d ]bis[1,3]-dithiol-4-yl)methane
—— (3S,4R)-1-Phenylsulfanyl-non-8-ene-3,4-diol 180693-06-5 C15H22O2S
(3S,4R)-1-Phenylsulfanyl-non-8-ene-3,4-diol
—— 4-[4-(4-Propan-2-yloxyphenyl)sulfanylphenyl]sulfanylbenzenethiol 203631-76-9 C21H20OS3
4-[4-(4-Propan-2-yloxyphenyl)sulfanylphenyl]sulfanylbenzenethiol
—— tert-butyl [(3S,4S)-4-(methoxymethoxy)-2,2-dimethyl-1-phenylsulfanylhex-5-en-3-yl] carbonate 150849-75-5 C21H32O5S
tert-butyl [(3S,4S)-4-(methoxymethoxy)-2,2-dimethyl-1-phenylsulfanylhex-5-en-3-yl] carbonate
—— 1-{2,6-dichloro-4-[(phenylthio)methyl]pyridin-3-yl}hept-6-en-1-one 607708-25-8 C19H19Cl2NOS
1-{2,6-dichloro-4-[(phenylthio)methyl]pyridin-3-yl}hept-6-en-1-one
—— 5-[1-hydroxy-1-(3,4-dimethoxy-2-methoxymethoxyphenyl)methyl]-4-[1-hydroxy-1-(4-methoxyphenyl)methyl]-1-methyl-2-phenylthio-1H-imidazole 445474-63-5 C29H32N2O7S
5-[1-hydroxy-1-(3,4-dimethoxy-2-methoxymethoxyphenyl)methyl]-4-[1-hydroxy-1-(4-methoxyphenyl)methyl]-1-methyl-2-phenylthio-1H-imidazole
—— [(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylsulfanyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-dimethyl-octoxysilane 157428-33-6 C24H40O5SSi
[(3aR,4R,6R,6aR)-2,2-dimethyl-4-phenylsulfanyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy-dimethyl-octoxysilane
—— 1H-Pyrazolo[1,5-b][1,2,4]triazole, 6-(1,1-dimethylethyl)-2-(methylthio)- 192578-76-0 C9H14N4S
1H-Pyrazolo[1,5-b][1,2,4]triazole, 6-(1,1-dimethylethyl)-2-(methylthio)-
—— 2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl 142010-85-3 C36H30O4S2
2,2'-Bis-methoxymethoxy-3,3'-bis-phenylsulfanyl-[1,1']binaphthalenyl
—— 3-Pyridin-2-ylsulfanylcyclohexan-1-one 153054-46-7 C11H13NOS
3-Pyridin-2-ylsulfanylcyclohexan-1-one
—— (1Z,3S)-3-hydroxy-1-(4'-methylphenylthio)-1-nitrobut-1-ene 160349-78-0 C11H13NO3S
(1Z,3S)-3-hydroxy-1-(4'-methylphenylthio)-1-nitrobut-1-ene