1896年,氟代乙酸乙酯的合成标志着有机氟化学研究的开端,至今已整整一个世纪。在此期间,几次重要的突破极大地推动了这一领域的发展,例如20世纪30年代氟里昂在制冷工业中的应用、二战期间曼哈顿工程的实施以及50年代高生理活性5-氟脲嘧啶的合成等。
我国拥有丰富的氟资源,已探明萤石储量约占世界总量的四分之一。然而直到20世纪50年代,中国在此领域的研究一片空白。当时国际形势的变化促使我国开始自主开发原子能技术,并急需一批特殊的含氟材料。从此,有机氟化学在中国的研究逐渐展开。中国科学院上海有机化学研究所因其在有机氟化学基础研究方面的卓越成就,被国际氟化学界誉为“上海氟化学”。
有机氟化合物又称氟碳化合物,是指分子结构中含C-F键的化合物,如四氟乙烯(CF2=CF2)。若碳氢化合物中的所有氢原子均被氟原子取代,则称为全氟化合物。由于氟是元素周期表中最电负、氧化性最强的原子,因此氟聚合物不易发生氧化裂解。此外,氟原子半径接近C-C键原子间距的一半,能紧密排列在碳原子周围,形成对C-C键的保护屏障,确保化学稳定性。C-F键具有极高的键能,赋予有机氟化物良好的热稳定性和抗氧化性。
许多含氟化合物被用于药物中,如全身麻醉剂氟烷、抗癌药5-氟尿嘧啶、镇静药氟奋乃静和抗精神病药氟哌啶醇等。根据结构不同,有机氟化合物大致可分为三类:
中文名称 | 英文名称 | CAS号 | 化学式 | 结构式图片 |
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—— | diphenyliodonium hexafluoroarsenate | 62613-15-4 | AsF6*C12H8I |
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—— | 3-fluoronitrobenzene radical anion | 34470-17-2 | C6H4FNO2 |
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—— | (2E)-methyl 3-(cinnamyloxy)acrylate | 147460-94-4 | C13H14O3 |
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—— | 6-fluoro-7-methylisatin 3-oxime | 275374-94-2 | C9H7FN2O2 |
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—— | <(S)-pyrrolidin-2-yl>benzyl alcohol | 74936-95-1 | C11H15NO |
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—— | methyl 5,5-difluoropiperidine-2-carboxylate | 1255663-85-4 | C7H11F2NO2 |
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—— | 3,3-difluoro-1-phenylcyclobutanecarboxylic acid | 1780846-70-9 | C11H10F2O2 |
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—— | 1,3-dibromo-4,6-bis(trifluoromethyl)benzene | 241151-55-3 | C8H2Br2F6 |
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—— | (3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-aminium hydrochloride | 1375470-88-4 | C14H17F3N2O*ClH |
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—— | 3-(benzyloxy)-4-fluorobenzonitrile | 1351862-19-5 | C14H10FNO |
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—— | Methyl 3-(2,4-dichloro-5-fluorophenyl)-2-[(4-fluorophenyl)iminomethyl]-3-hydroxyprop-2-enoate | 176637-98-2 | C17H11Cl2F2NO3 |
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—— | N-methyl-N-(2,2,2-trifluoroethyl)piperidin-4-amine hydrochloride | 1432678-56-2 | C8H16ClF3N2 |
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—— | 1-(2,2-difluoroethyl)-1H-pyrazol-3-amine | 1006462-38-9 | C5H7F2N3 |
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—— | 3-[2-(4-acetyl-2-chloro-phenoxy)-ethoxy]-7-chloro-2-(3,4-difluoro-phenyl)-1-methyl-1H-quinolin-4-one | 851135-07-4 | C26H19Cl2F2NO4 |
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—— | N-(2,2-difluoroethyl)-1-methylpiperidin-4-amine | 1184221-15-5 | C8H16F2N2 |
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—— | 1-[8-(4-Fluorophenyl)-1,4-dioxaspiro[4.5]dec-8-yl]methanamine | 78228-02-1 | C15H20FNO2 |
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—— | 3-(α,α,α-Trifluoromethyl)nitrobenzene radical anion | 34526-71-1 | C7H4F3NO2 |
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—— | 8-bromo-1,1,1-trifluorooctane | 407-67-0 | C8H14BrF3 |
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—— | 1-(difluoromethyl)-1H-pyrazole-4-carbaldehyde | 1216244-84-6 | C5H4F2N2O |
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—— | potassium trifluoro(prop-1-yn-1-yl)borate | 1500106-31-9 | C3H3BF3*K |
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—— | tert-butyl 4-[(2,2,2-trifluoroethyl)amino]piperidine-1-carboxylate | 1146289-88-4 | C12H21F3N2O2 |
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—— | 1-hexyl-1-methylpyrrolidinium bis(trifluoromethylsulfonyl)imide | 380497-19-8 | C2F6NO4S2*C11H24N |
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—— | 2-fluoro-5-[(E)-(3-oxo-2-benzofuran-1-ylidene)methyl]benzonitrile | 763114-25-6 | C16H8FNO2 |
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—— | Sodium 1-(dimethoxyphosphoryl)-3,3-difluoro-3-phenylprop-1-en-2-olate | 1055985-86-8 | C11H12F2O4P*Na |
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—— | 1-(2-fluorophenyl)-2-methylpropan-2-amine | 1840-77-3 | C10H14FN |
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—— | (Trifluoromethylthio) silver(I) | 811-68-7 | CHAgF3S |
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—— | 2-Bromo-4-chloro-6-fluorotoluene | 1082040-50-3 | C7H5BrClF |
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—— | Sodium 2,4-difluorobenzoate | 83198-07-6 | C7H3F2O2*Na |
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—— | Diphenyliodonium hexafluoroarsenate(1-) | 62613-15-4 | C12H10AsF6I |
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—— | Propane, 2,3-dibromo-1,1,1-trifluoro- | 431-21-0 | C3H3Br2F3 |
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—— | 4-(difluoromethylidene)piperidine hydrochloride | 208245-66-3 | C6H9F2N*ClH |
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—— | 2,3,4,5-tetrafluorobenzoic acid sodium salt | 67852-79-3 | C7HF4O2*Na |
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—— | 1-(4-Fluoro benzyl)cyclopropylamine | 864961-01-3 | C10H12FN |
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—— | N-(2,2-Difluoroethyl)piperidin-4-amine | 1378792-60-9 | C7H14F2N2 |
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—— | (E)-3-Chloro-3-(4-fluoro-phenyl)-acrylonitrile | 126417-76-3 | C9H5ClFN |
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—— | (E)-N-[(2-chloro-6-fluorophenyl)methylidene]hydroxylamine | 443-33-4 | C7H5ClFNO |
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—— | Dichloromethyl(3,3,4,4,5,5,6,6,6-nonafluorohexyl)silane | 38436-16-7 | C7H5Cl2F9Si |
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—— | (trans-4-(trifluoromethyl)cyclohexyl)methanol | 1202577-61-4 | C8H13F3O |
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—— | 2-Methyl-6-(trifluoromethyl)benzoic acid | 1104383-68-7 | C9H7F3O2 |
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—— | 4-(difluoromethoxy)-2-fluoroaniline | 1003865-65-3 | C7H6F3NO |
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—— | (S)-2-((tert-butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid | 181128-25-6 | C9H14F3NO4 |
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—— | 4-bromo-3-fluoro-2-methoxyaniline | 1137869-95-4 | C7H7BrFNO |
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—— | 2-(3-bromophenyl)-2,2-difluoroethan-1-ol | 915133-40-3 | C8H7BrF2O |
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—— | sodium salt of 2,3,4-trifluorobenzoic acid | 402955-41-3 | C7H2F3O2*Na |
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—— | methylpiperidin-4-amine hydrochloride | 1193-03-9 | C6H14N2*ClH |
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—— | milvexian | 1802425-99-5 | C28H23Cl2F2N9O2 |
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—— | (1R)-1-cyclopropyl-2,2,2-trifluoroethanamine hydrochloride | 1160756-75-1 | C5H8F3N*ClH |
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—— | 2-bromo-4-chloro-1-(difluoromethyl)benzene | 1261476-50-9 | C7H4BrClF2 |
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—— | Boronic acid, B-[3-[[(2-bromo-4-methylphenyl)amino]carbonyl]-2-fluorophenyl]- | 2096336-37-5 | C14H12BBrFNO3 |
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—— | 1-Benzyl-4-(bromomethyl)-2,3,5,6-tetrafluorobenzene | 776-40-9 | C14H9BrF4 |
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