CN108467408A - 一种具有羟基苯基官能团的二芳基磷化合物及其制备方法 - Google Patents
一种具有羟基苯基官能团的二芳基磷化合物及其制备方法 Download PDFInfo
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- -1 diaryl phosphorus compound Chemical class 0.000 title claims abstract description 42
- 239000011574 phosphorus Substances 0.000 title claims abstract description 17
- 229910052698 phosphorus Inorganic materials 0.000 title claims abstract description 17
- 125000000524 functional group Chemical group 0.000 title claims abstract description 16
- 125000004464 hydroxyphenyl group Chemical group 0.000 title claims abstract description 15
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 45
- 238000000926 separation method Methods 0.000 claims abstract description 15
- DBWGAXVWWNKFNI-UHFFFAOYSA-N [O].C1(=CC=CC=C1)[P]C1=CC=CC=C1 Chemical compound [O].C1(=CC=CC=C1)[P]C1=CC=CC=C1 DBWGAXVWWNKFNI-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000002989 phenols Chemical class 0.000 claims abstract description 7
- 239000000376 reactant Substances 0.000 claims abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 16
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 238000004440 column chromatography Methods 0.000 claims description 14
- 238000001914 filtration Methods 0.000 claims description 14
- 239000007788 liquid Substances 0.000 claims description 14
- 239000012074 organic phase Substances 0.000 claims description 14
- 238000010791 quenching Methods 0.000 claims description 14
- 230000000171 quenching effect Effects 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 6
- 150000007529 inorganic bases Chemical class 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 3
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 2
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 claims description 2
- 239000001488 sodium phosphate Substances 0.000 claims description 2
- 229910000162 sodium phosphate Inorganic materials 0.000 claims description 2
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims 1
- ZNSDNJGLCKLLQW-UHFFFAOYSA-N [O].C1(=CC=CC=C1)[P] Chemical compound [O].C1(=CC=CC=C1)[P] ZNSDNJGLCKLLQW-UHFFFAOYSA-N 0.000 claims 1
- 229910052700 potassium Inorganic materials 0.000 claims 1
- 239000011591 potassium Substances 0.000 claims 1
- 239000003054 catalyst Substances 0.000 abstract description 7
- 239000003446 ligand Substances 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 abstract description 5
- 239000002994 raw material Substances 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 230000009257 reactivity Effects 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 38
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 36
- 150000002903 organophosphorus compounds Chemical class 0.000 description 17
- 238000005481 NMR spectroscopy Methods 0.000 description 16
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 14
- 238000004679 31P NMR spectroscopy Methods 0.000 description 14
- 238000005160 1H NMR spectroscopy Methods 0.000 description 12
- 125000004963 sulfonylalkyl group Chemical group 0.000 description 12
- JPJGNZQDELRZGE-UHFFFAOYSA-N (phenyl-$l^{2}-phosphanyl)benzene Chemical compound C=1C=CC=CC=1[P]C1=CC=CC=C1 JPJGNZQDELRZGE-UHFFFAOYSA-N 0.000 description 11
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 11
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 238000000034 method Methods 0.000 description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 7
- 239000005864 Sulphur Substances 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000004079 fireproofing Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- 229910000160 potassium phosphate Inorganic materials 0.000 description 2
- 235000011009 potassium phosphates Nutrition 0.000 description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- OYYSQSHXTLAXKU-UHFFFAOYSA-N CC(C1=CC=CC=C1O)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3 Chemical compound CC(C1=CC=CC=C1O)P(=O)(C2=CC=CC=C2)C3=CC=CC=C3 OYYSQSHXTLAXKU-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 238000005654 Michaelis-Arbuzov synthesis reaction Methods 0.000 description 1
- 238000007014 Michaelis-Becker reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001499 aryl bromides Chemical class 0.000 description 1
- 125000000958 aryl methylene group Chemical group 0.000 description 1
- JPUUAYFQHNNDBM-UHFFFAOYSA-N bicyclo[4.1.0]hepta-1(6),3-diene-2,5-dione Chemical compound O=C1C=CC(=O)C2=C1C2 JPUUAYFQHNNDBM-UHFFFAOYSA-N 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000005204 hydroxybenzenes Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000003863 metallic catalyst Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/50—Organo-phosphines
- C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
- C07F9/5333—Arylalkane phosphine oxides or thioxides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
- C07F9/65515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring
- C07F9/65517—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
本发明涉及化学合成技术领域，特别涉及一种具有羟基苯基官能团的二芳基磷化合物及其制备方法，以酚类化合物和二苯基磷氧为反应物制备而得。本发明产物含双官能团，在催化剂，配体领域有潜在应用。反应条件温和，反应活性高，原料转化完全，分离方便，能获得高纯度的产物。能以高收率得到一系列具有羟基苯基官能团的二芳基磷化合物。并且，在扩大规模反应中，底物反应活性仍能保持。
Description
技术领域
本发明涉及化学合成技术领域，特别涉及一种具有羟基苯基官能团的二芳基磷化合物及其制备方法。
背景技术
有机磷化合物广泛应用于杀虫剂、增塑剂、络合物催化剂配体、农药、医药、化学材料，防火材料等各种产品中。近年来，有机磷化合物作为有机催化剂和配体，广泛地应用于合成化学，因此得到许多合成化学家的广泛关注。到目前为止，已经发展了一系列方法来合成有机磷化合物。鉴于有机磷化合物在合成化学中的重要意义，发展可靠且高产率的构建有机磷化合物，尤其是磷氧化合物的方法是目前研究的热点和难点。传统的通过碳-磷键形成反应合成有机磷氧化合物的方法包括Michaelis-Arbuzov、Michaelis-Becker反应及FeCl3参与的Friedel-Crafts反应。如文献1：(a)Bhattacharya,A.K.Chem. Rev.1981,81,415；(b)Demmer,C.S.；Krogsgaard-Larsen,N.； Bunch,L.Chem.Rev.2011,111,7981；(c)Rajeshwaran,G.G.； Nandakumar,M.；Sureshbabu,R.；Mohanakrishnan,A.K.Org.Lett.2011,13,1270-1273.(d)Pallikonda,G.；Chakravarty,M.Eur. J.Org.Chem.2013,2013,944-951.但是，这些方法存在底物范围窄，反应条件苛刻等问题。2014年，Walsh等人发展了采用过渡金属 Pd和双膦配体为催化剂，催化芳基溴和含磷有机物的偶联反应可以方便的构建该类含磷有机物。(文献2：Montel,S.；Jia,T.；Walsh, P.J.Org.Lett.2014,16,130-133.)但是反应必须采用贵金属做为催化剂，因而限制了该类反应的应用。最近，Anand小组和Kang 小组分别发展了基于对亚甲基醌的1，6-氢磷化反应构建含有双芳基亚甲基的亚磷酸酯类化合物。(文献3：(a)Arde,P.；VijayaAnand, R.Org.Biomol.Chem.2016,14,5550-5554；(b)Molleti,N.；Kang, J.Y.Org.Lett.2017,19,958-961.)该类方法不需要使用过渡金属催化剂，但是底物范围比较窄，而且反应原料中具有两个叔丁基取代基，需要额外的步骤将其脱除，也限制了该类反应的应用。因此，发展更加高效，易于操作的构建有机磷氧化合物的方法是十分必要的。
发明内容
为解决上述技术问题，本发明提供了一种具有羟基苯基官能团的二芳基磷化合物的制备方法。
具体技术方案如下：
一种具有羟基苯基官能团的二芳基磷化合物，结构通式为：
所述R1为C1-C6的烷基；苯基及含有取代基的苯环，取代基为 C1-C6的烷基、三氟甲基、甲氧基中的一种或几种；
所述R2为C1-C6的烷基；苯基及含有取代基的苯环，取代基为 F、Cl、Br、Me、MeO中的一种或几种；
具有羟基苯基官能团的二芳基磷化合物的制备方法，以酚类化合物和二苯基磷氧为反应物，按照如下反应制备：
所述R1为C1-C6的烷基；苯基及含有取代基的苯环，取代基为 C1-C6的烷基、三氟甲基、甲氧基中的一种或几种；
所述R2为C1-C6的烷基；苯基及含有取代基的苯环，取代基为 F、Cl、Br、Me、MeO的一种或几种；
具体反应步骤为：
将酚类化合物溶于浓度为0.01～1.0mol/L的有机溶剂中，向该体系按一定比例加入二苯基磷氧，然后向该反应混合物中按一定比例加入无机碱，在30～150℃下搅拌反应1～48小时，反应完毕后加水淬灭，静置分液，水层用二氯甲烷萃取2～8次，合并有机相，最后用无水硫酸钠干燥、过滤，减压除去溶剂后柱层析或重结晶得到具有羟基苯基官能团的二芳基磷化合物。
所述酚类化合物、二苯基磷氧与无机碱的摩尔比为1:(0.8～2.0): (0.8～2.0)。
所述有机溶剂为四氢呋喃、二氯甲烷、甲苯、1,4-二氧六环、苯中的一种或几种。
所述无机碱为促进剂，可以为碳酸钾、碳酸钠、碳酸铯、氢氧化钠、氢氧化钾、磷酸钠、磷酸钾中的一种或几种。本方法的优点是：
本方法原料廉价易得，性质稳定，反应采用条件温和，化学选择性好，能获得高纯度的产物。不需要采用贵金属催化剂，而且底物范围宽，能以高收率得到一系列具有羟基苯基官能团的二芳基磷化合物。在扩大规模反应中，底物反应活性仍能保持取得优秀的收率。得到的具有羟基苯基官能团的二芳基磷化合物含双官能团，可以应用于催化剂，和配体领域的开发以及防火材料的研究。
附图说明
图1为实施例1中产物的核磁共振氢谱；
图2为实施例2中产物的核磁共振氢谱；
图3为实施例3中产物的核磁共振氢谱；
图4为实施例4中产物的核磁共振氢谱；
图5为实施例5中产物的核磁共振氢谱；
图6为实施例6中产物的核磁共振氢谱；
图7为实施例7中产物的核磁共振氢谱；
图8为实施例8中产物的核磁共振氢谱；
图9为实施例9中产物的核磁共振氢谱；
图10为实施例10中产物的核磁共振氢谱；
图11为实施例11中产物的核磁共振氢谱；
图12为实施例12中产物的核磁共振氢谱。
具体实施方式
下面结合附图和实施例对本发明进行详细说明，但本发明的保护范围不受附图和实施例所限。
实施例1：
将磺酰烷基取代苯酚类化合物(0.5mmol)溶于5mL的甲苯中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入碳酸钾(0.5mmol)，反应在30℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取4次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(180.8mg, 产率80％)。其结构式为图1为实施例1中产物的核磁共振氢谱，通过图1中核磁共振氢谱的化学位移值和积分比例可以推测其为图1所示结构。再结合13C NMR、31P NMR、19F NMR以及高分辨质谱(HRMS)进一步确定其结构，具体的结构鉴定数据为：
((2-Hydroxyphenyl)(4-(trifluoromethyl)phenyl)methyl)diphenylphosphine oxide:1H NMR(400MHz,CDCl3)δ10.02(s,1H), 7.76–7.70(m,2H),7.62–7.50(m,4H),7.49–7.28(m,9H), 7.03(t,J＝7.8Hz,1H),6.88(d,J＝8.1Hz,1H),6.70(t, J＝7.5Hz,1H),5.12(d,JH-P＝10.9Hz,1H)；13C NMR(100MHz, CDCl3)δ155.2(d,JC-P＝5.8Hz),140.2(d,JC-P＝2.9Hz), 132.3(d,JC-P＝2.8Hz),132.2(d,JC-P＝2.9Hz),131.8(d, JC-P＝7.6Hz),131.2(d,JC-P＝19.5Hz),131.2,130.9(d,JC-P ＝5.4Hz),130.7,130.2(d,JC-P＝6.1Hz),129.9(d,JC-P＝ 4.6Hz),129.3,129.0(d,JC-P＝13.1Hz),128.7(d,JC-P＝1.7 Hz),128.6(d,JC-P＝1.8Hz),125.4,125.2(q,JC-F＝4.0Hz), 123.0(d,JC-P＝4.4Hz),122.7,120.4,118.6,50.3(d,JC-P ＝66.1Hz)；31P NMR(162MHz,CDCl3)δ37.1；19F NMR(376MHz, CDCl3)δ-62.6；IR(KBr):3428,3061,1619,1455,1439,1325, 1167,1121,1068,761,726,699,557；HRMS(ESI)calcd for C26H21F3O2P[(M+H)]+:453.1226,found:453.1223.
实施例2：
将磺酰烷基取代苯酚类化合物(0.5mmol)溶于5mL的四氢呋喃中，向该体系中加入0.4mmol二苯基磷氧。接着向该反应混合物中加入碳酸钾(0.4mmol)，反应在60℃下搅拌反应1小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取8次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物 (186.4mg,产率87％)，其结构式为图2为实施例2 中产物的核磁共振氢谱，如图所示，图2中核磁共振氢谱的化学位移值和积分比例可以推测其为上述结构式所示结构。再结合13C NMR、 31P NMR以及HRMS进一步确定其结构。具体的结构鉴定数据为：
((2-Hydroxy-4-methoxyphenyl)(p-tolyl)methyl)diphenylpho sphine oxide:1H NMR(400MHz,CDCl3)δ10.80(s,1H), 7.76–7.67(m,2H),7.60–7.55(m,2H),7.48–7.41(m,2H), 7.39–7.32(m,4H),7.23–7.20(m,2H),6.95–6.90(m,3H), 6.47(d,J＝2.6Hz,1H),6.27–6.24(m,1H),4.73(d,JH-P＝ 12.7Hz,1H),3.67(s,3H),2.21(s,3H)；13C NMR(100MHz,CDCl3) δ160.4(d,JC-P＝1.4Hz),157.0(d,JC-P＝4.6Hz),136.7 (d,JC-P＝2.0Hz),132.9(d,JC-P＝8.9Hz),132.9(d,JC-P ＝3.6Hz),132.1(d,JC-P＝5.4Hz),132.1,131.4(d,JC-P＝ 9.2Hz),131.2(d,JC-P＝8.8Hz),130.8(d,JC-P＝97.8Hz), 130.4(d,JC-P＝98.5Hz),129.5(d,JC-P＝6.1Hz),129.2(d, JC-P＝1.3Hz),128.5(d,JC-P＝2.2Hz),128.5(d,JC-P＝25.8 Hz),116.0(d,JC-P＝4.6Hz),107.0,104.4(d,JC-P＝1.5Hz), 55.1,52.5(d,JC-P＝65.6Hz),21.0；31P NMR(162MHz,CDCl3) δ38.7；IR(KBr):3412,3058,3007,2940,2898,1736,1615, 1524,1437,1153,1036,854,802,720,696,536；HRMS(ESI) calcdfor C27H26O3P[(M+H)]+:429.1614,found:429.1617.
实施例3：
将磺酰烷基取代苯酚类化合物(0.5mmol)溶于5mL的乙酸乙酯中，向该体系中加入1mmol二苯基磷氧。接着向该反应混合物中加入碳酸铯(1mmol)，反应在90℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取6次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物 (135.4mg,产率84％)。其结构式为具体的结构鉴定数据为：
(1-(2-Hydroxyphenyl)ethyl)diphenylphosphine oxide:1H NMR(400MHz,CDCl3)δ10.20(s,1H),7.94–7.80(m,2H), 7.70–7.48(m,5H),7.47–7.28(m,3H),7.13–7.04(m,1H), 6.96–6.93(m,1H),6.84–6.81(m,1H),6.67(t,J＝7.4Hz, 1H),3.64(dt,J＝9.4,7.4Hz,1H),1.59(dd,J＝15.9,7.5 Hz,3H)；13C NMR(100MHz,CDCl3)δ156.3(d,JC-P＝4.1Hz), 132.3(d,JC-P＝2.9Hz),132.0(d,JC-P＝2.8Hz),131.3(d, JC-P＝7.3Hz),131.2(d,JC-P＝8.9Hz),130.9(d,JC-P＝9.1 Hz),130.2(d,JC-P＝6.5Hz),129.2,128.9(d,JC-P＝2.1Hz), 128.9(d,JC-P＝11.5Hz),128.5(d,JC-P＝11.7Hz),124.5(d, JC-P＝5.8Hz),120.2,119.9(d,JC-P＝2.1Hz),40.7(d,JC-P ＝67.2Hz),13.0(d,JC-P＝2.2Hz)；31P NMR(162MHz,CDCl3) δ41.6；IR(KBr):3426,3060,2961,1592,1451,1437,1390, 1158,1119,1091,1020,778,751,721,696,605,556；HRMS(ESI) calcd for C20H20O2P[(M+H)]+:323.1195,found:323.1196.
实施例4：
将磺酰烷基取代苯酚类化合物(0.5mmol)溶于5mL的二氯甲烷中，向该体系中加入0.4mmol二苯基磷氧。接着向该反应混合物中加入氢氧化钠(1mmol)，反应在150℃下搅拌反应24小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取8次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(177.8mg,产率83％)。其结构式为具体的结构鉴定数据为： ((6-Hydroxybenzo[d][1,3]dioxol-5-yl)(phenyl)methyl)diphenyl phosphine oxide:1H NMR(400MHz,DMSO-d6)δ9.64(s,1H),7.84–7.78(m,2H),7.73–7.64(m,2H),7.58–7.56(m,1H), 7.52–7.31(m,8H),7.17–7.13(m,2H),7.12–7.04(m,1H), 6.35–6.34(m,1H),5.86–5.80(m,2H),5.54(d,JH-P＝9.6Hz, 1H)；13C NMR(100MHz,DMSO-d6)δ149.3(d,JC-P＝8.2Hz), 146.2,139.5,137.5(d,JC-P＝4.1Hz),133.6(d,JC-P＝15.8 Hz),132.6(d,JC-P＝15.7Hz),131.5(d,JC-P＝2.6Hz),131.3 (d,JC-P＝2.4Hz),131.4(d,JC-P＝14.7Hz),130.5(d,JC-P ＝32.2Hz),130.5(d,JC-P＝14.8Hz),129.6(d,JC-P＝6.2Hz), 128.4(d,JC-P＝4.5Hz),128.4(d,JC-P＝27.0Hz),128.0,126.4, 115.7(d,JC-P＝3.3Hz),109.2(d,JC-P＝5.5Hz),100.6,97.5,42.3(d,JC-P＝68.2Hz)；31P NMR(162MHz,DMSO-d6)δ31.7； IR(KBr):3431,3057,2926,1626,1504,1438,1289,1158,1118, 1040,942,872,742,723,540；HRMS(ESI)calcd forC26H22O4P [(M+H)]+:429.1256,found:429.1251.
实施例5：
将磺酰烷基取代苯酚类化合物0.5mmol溶于0.5mL的1,4-二氧六环中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入氢氧化钾0.5mmol，反应在60℃下搅拌反应48小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取5次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(192.5mg,产率84％)。其结构式为具体的结构鉴定数据为：
((6-Hydroxybenzo[d][1,3]dioxol-5-yl)(4-methoxyphenyl)me thyl)diphenylphosphine oxide:1H NMR(400MHz,DMSO-d6)δ9.58 (s,1H),7.80–7.75(m,2H),7.70–7.65(m,2H),7.53–7.32(m, 9H),6.75–6.68(m,2H),6.31(s,1H),5.82(m,2H),5.46(d, JH-P＝9.8Hz,1H),3.63(s,3H)；13C NMR(100MHz,DMSO-d6) δ158.2,149.7(d,JC-P＝7.8Hz),146.6,140.0,134.2(d,JC-P ＝15.5Hz),133.3(d,JC-P＝16.4Hz),131.8(d,JC-P＝12.2 Hz),131.1(d,JC-P＝4.5Hz),131.1,130.9(d,JC-P＝8.6Hz), 129.9(d,JC-P＝4.0Hz),128.9(d,JC-P＝1.3Hz),128.9(d, JC-P＝20.2Hz),116.7(d,JC-P＝2.9Hz),114.0,109.6(d,JC-P ＝3.8Hz),101.1,98.0,55.4,41.8(d,JC-P＝69.2Hz)；31P NMR(162MHz,DMSO-d6)δ31.9；IR(KBr):3425,3061,2960,2903, 1607,1509,1439,1245,1174,1154,1113,1048,942,877,833, 727,700,593,542,523；HRMS(ESI)calcd for C27H24O5P[(M+H)]+: 459.1356,found:459.1354.
实施例6：
将磺酰烷基取代苯酚类化合物0.5mmol溶于5mL的苯中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入磷酸钠0.5mmol，反应在60℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取6次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(176.8mg,产率92％)。其结构式为具体的结构鉴定数据为：
((2-Hydroxyphenyl)(phenyl)methyl)diphenylphosphine oxide:1H NMR(400MHz,DMSO-d6)δ9.85(s,1H),8.01(d,J ＝7.6Hz,1H),7.83–7.77(m,2H),7.75–7.65(m,2H), 7.48–7.34(m,8H),7.17–7.13(m,2H),7.12–7.03(m,1H), 6.96–6.92(m,1H),6.72–6.68(m,2H),5.62(d,JH-P＝9.2Hz, 1H)；13C NMR(100MHz,DMSO-d6)δ154.9(d,JC-P＝7.9Hz), 137.8(d,JC-P＝4.4Hz),134.1(d,JC-P＝12.2Hz),133.1(d, JC-P＝12.4Hz),131.9(d,JC-P＝2.3Hz),131.8(d,JC-P＝2.3 Hz),131.2(d,JC-P＝8.7Hz),130.9(d,JC-P＝8.7Hz),130.7 (d,JC-P＝5.7Hz),130.3(d,JC-P＝6.3Hz),128.8(d,JC-P ＝18.5Hz),128.8(d,JC-P＝4.1Hz),128.5,128.4,126.9,125.0 (d,JC-P＝3.1Hz),119.5,115.7,43.2(d,JC-P＝68.2Hz)；31P NMR(162MHz,DMSO-d6)δ31.3；IR(KBr):3413,3058,1576,1485,1437,1275,1248,1144,1119,811,750,691,560,530；HRMS(ESI) calcd for C25H22O2P[(M+H)]+:385.1352,found:385.1352.
实施例7：
将磺酰烷基取代苯酚类化合物(0.5mmol)溶于50mL的甲苯中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入磷酸钾(0.5mmol)，反应在60℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取4次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(179.3 mg,产率90％)。其结构式为具体的结构鉴定数据为：
((2-Hydroxyphenyl)(m-tolyl)methyl)diphenylphosphine oxide:1H NMR(400MHz,DMSO-d6)δ9.85(s,1H),7.99(d,J ＝7.6Hz,1H),7.86–7.75(m,2H),7.75–7.63(m,2H), 7.45–7.35(m,6H),7.29(d,J＝7.8Hz,1H),7.24(s,1H),7.04 (t,J＝7.6Hz,1H),6.99–6.84(m,2H),6.72–6.68(m 2H),5.58 (d,JH-P＝9.3Hz,1H),2.13(s,3H)；13C NMR(100MHz,DMSO-d6) δ154.9(d,JC-P＝7.7Hz),137.7(d,JC-P＝4.3Hz),137.4, 134.1(d,JC-P＝12.8Hz),133.2(d,JC-P＝13.1Hz),131.8(d, JC-P＝9.5Hz),131.8(d,JC-P＝4.1Hz),131.2(d,JC-P＝8.8 Hz),130.9,130.9,130.9,130.8,130.8,128.8(d,JC-P＝5.5Hz),128.8(d,JC-P＝17.0Hz),128.4,127.6,127.4(d,JC-P ＝6.1Hz),124.9(d,JC-P＝3.1Hz),119.5,115.8,43.1(d,JC-P ＝68.0Hz),21.5；31P NMR(162MHz,DMSO-d6)δ31.3；IR(KBr): 3426,3071,3011,2951,2926,2737,1603,1487,1457,1437,1383, 1275,1241,1158,821,718,610,568,528,513；HRMS(ESI)calcd for C26H24O2P[(M+H)]+:399.1508,found:399.1506.
实施例8：
将磺酰烷基取代苯酚类化合物(0.5mmol)溶于5mL的甲苯中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入碳酸钠(0.5mmol)，反应在60℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取6次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(175.3 mg,产率88％)。其结构式为具体的结构鉴定数据为：
((2-Hydroxyphenyl)(o-tolyl)methyl)diphenylphosphine oxide:1H NMR(400MHz,DMSO-d6)δ9.75(s,1H),8.07(d,J ＝7.8Hz,1H),7.88(d,J＝7.7Hz,1H),7.78–7.68(m,2H), 7.55–7.38(m,6H),7.36–7.31(m,2H),7.12(t,J＝7.5Hz, 1H),7.02(t,J＝7.4Hz,1H),6.98–6.89(m,2H),6.74–6.63 (m,2H),5.66(d,JH-P＝9.5Hz,1H),2.16(s,3H)；13C NMR(100 MHz,DMSO-d6)δ154.8(d,JC-P＝7.4Hz),137.0(d,JC-P＝7.8 Hz),136.5(d,JC-P＝3.6Hz),133.9(d,JC-P＝95.5Hz),133.2 (d,JC-P＝96.6Hz),131.9(d,JC-P＝2.8Hz),131.8(d,JC-P ＝2.7Hz),131.3(d,JC-P＝8.7Hz),131.1(d,JC-P＝5.4Hz), 131.0(d,JC-P＝8.8Hz),130.6(d,JC-P＝5.1Hz),130.3,128.8 (d,JC-P＝2.3Hz),128.6(d,JC-P＝2.3Hz),128.2,127.0,126.1, 124.4(d,JC-P＝3.9Hz),119.4,115.2,38.5(d,JC-P＝68.4 Hz),19.9；31P NMR(162MHz,DMSO-d6)δ31.4；IR(KBr):3435, 3039,2955,2733,1596,1488,1457,1438,1383,1277,1157,1112, 849,785,697,560,527；HRMS(ESI)calcd forC26H24O2P[(M+H)]+: 399.1508,found:399.1508.
实施例9：
将磺酰烷基取代苯酚类化合物(0.5mmol)溶于5mL的甲苯中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入碳酸钾(0.5mmol)，反应在60℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取5次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(183.6 mg,产率88％)。其结构式为具体的结构鉴定数据为：
((6-Hydroxybenzo[d][1,3]dioxol-5-yl)(p-tolyl)methyl)diphenylphosphine oxide:1H NMR(400MHz,CDCl3)δ10.40(s,1H), 7.74–7.65(m,2H),7.62–7.52(m,2H),7.51–7.44(m,2H), 7.41–7.33(m,4H),7.24–7.16(m,2H),6.97–6.93(m,2H),6.49–6.45(m,2H),5.86–5.74(m,2H),4.66(d,JH-P＝13.5 Hz,1H),2.23(s,3H)；13C NMR(100MHz,CDCl3)δ151.2(d, JC-P＝4.9Hz),147.9(d,JC-P＝1.2Hz),141.0,136.9(d,JC-P＝1.8Hz),132.7(d,JC-P＝3.3Hz),132.1(d,JC-P＝4.9Hz), 132.1,131.4(d,JC-P＝9.2Hz),131.2(d,JC-P＝8.8Hz),130.7 (d,JC-P＝98.2Hz),130.4(d,JC-P＝98.1Hz),129.6(d,JC-P ＝6.4Hz),129.2,128.7,128.5,128.4,115.2(d,JC-P＝4.8Hz), 110.5(d,JC-P＝8.8Hz),101.5(d,JC-P＝1.5Hz),101.1,52.4 (d,JC-P＝65.8Hz),21.0；31P NMR(162MHz,CDCl3)δ38.6； IR(KBr):3422,3055,2923,1623,1504,1438,1158,1039,938,975,721,696,538；HRMS(ESI)calcd for C27H24O4P[(M+H)]+: 443.1407,found:443.1406.
实施例10：
将磺酰烷基取代苯酚类化合物(0.5mmol)溶于5mL的甲苯中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入碳酸钾(0.5mmol)，反应在60℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取5次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(169.3 mg,产率85％)。其结构式为具体的结构鉴定数据为：
((2-Hydroxyphenyl)(p-tolyl)methyl)diphenylphosphine oxide:1H NMR(400MHz,CDCl3)δ10.54(s,1H),7.76–7.65(m, 2H),7.65–7.54(m,2H),7.51–7.40(m,2H),7.38–7.33(m,4H), 7.27–7.24(m,2H),7.07–7.03(m,2H),6.96–6.88(m,3H), 6.67(t,J＝7.4Hz,1H),4.80(d,JH-P＝12.4Hz,1H),2.22 (s,3H)；13C NMR(100MHz,CDCl3)δ155.8(d,JC-P＝4.6Hz), 136.8(d,JC-P＝1.9Hz),132.6(d,JC-P＝4.0Hz),132.3(d, JC-P＝8.6Hz),132.1(d,JC-P＝1.8Hz),132.1(d,JC-P＝7.7 Hz),131.4(d,JC-P＝9.2Hz),131.2(d,JC-P＝8.8Hz),130.7 (d,JC-P＝98.1Hz),130.4(d,JC-P＝99.1Hz),129.6(d,JC-P ＝6.2Hz),129.2(d,JC-P＝1.0Hz),129.2(d,JC-P＝1.0Hz), 128.5(d,JC-P＝3.5Hz),128.5(d,JC-P＝20.2Hz),123.7(d, JC-P＝4.7Hz),120.2,119.8(d,JC-P＝1.2Hz),53.1(d,JC-P＝65.3Hz),21.0；31P NMR(162MHz,CDCl3)δ38.3；IR(KBr): 3421,3062,2925,2739,1596,1511,1456,1438,1386,1154,852, 792,753,723,560,530,494；HRMS(ESI)calcd forC26H24O2P [(M+H)]+:399.1508,found:399.1510.
实施例11：
将磺酰烷基取代苯酚类化合物0.5mmol溶于5mL的甲苯中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入碳酸钾(0.5mmol)，反应在60℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取7次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(189.9mg, 产率82％)。其结构式为具体的结构鉴定数据为：
((4-Bromo-2-hydroxyphenyl)(phenyl)methyl)diphenylphosph ine oxide:1HNMR(400MHz,DMSO-d6)δ10.35(s,1H), 7.99–7.96(m,1H),7.83–7.78(m,2H),7.74–7.68(m,2H), 7.52–7.34(m,8H),7.18–7.07(m,2H),7.12–7.05(m,1H), 6.94–6.91(m,1H),6.89–6.87(m,1H),5.56(d,JH-P＝9.1Hz, 1H)；13C NMR(100MHz,DMSO-d6)δ156.2(d,JC-P＝7.7Hz), 137.2(d,JC-P＝4.4Hz),133.8(d,JC-P＝23.3Hz),132.8(d, JC-P＝24.3Hz),132.3(d,JC-P＝5.5Hz),132.1(d,JC-P＝2.9 Hz),131.9(d,JC-P＝2.6Hz),131.2(d,JC-P＝8.7Hz),130. 9(d,JC-P＝8.8Hz),130.2(d,JC-P＝6.2Hz),128.9(d,JC-P ＝3.2Hz),128.9(d,JC-P＝26.0Hz),128.6,127.1,124.7(d, JC-P＝3.2Hz),122.3,120.7,118.3,42.7(d,JC-P＝67.5Hz)； 31P NMR(162MHz,DMSO-d6)δ31.5；IR(KBr):3422,3025,2901,2718,1589,1491,1419,1260,1145,1116,1095,1072,887,859, 837,726,537,501；HRMS(ESI)calcd for C25H21BrO2P[(M+H)]+: 463.0457,found:463.0453.
实施例12：
将磺酰烷基取代苯酚类化合物0.5mmol溶于5mL的甲苯中，向该体系中加入0.5mmol二苯基磷氧。接着向该反应混合物中加入碳酸钾0.5mmol，反应在60℃下搅拌反应12小时。反应完毕后加水淬灭；静置分液，水层用二氯甲烷萃取3次，合并有机相，无水硫酸钠干燥，过滤，减压除去溶剂后柱层析得到有机磷化合物(178.2mg, 产率86％)。其结构式为具体的结构鉴定数据为：
((2-Hydroxyphenyl)(4-methoxyphenyl)methyl)diphenylphosp hine oxide:1HNMR(400MHz,CDCl3)δ10.54(s,1H),7.75–7.67 (m,2H),7.62–7.54(m,2H),7.49–7.41(m,2H),7.39–7.33(m, 4H),7.30–7.26(m,2H),7.08–7.03(m,2H),6.92–6.88(m,1H), 6.72–6.64(m,3H),4.78(d,JH-P＝12.4Hz,1H),3.70(s,3H)； 13C NMR(100MHz,CDCl3)δ158.6(d,JC-P＝1.7Hz),155.7(d, JC-P＝4.7Hz),132.2(d,JC-P＝8.8Hz),132.1(d,JC-P＝7.0Hz),132.1(d,JC-P＝1.2Hz),131.4(d,JC-P＝9.2Hz),131.2 (d,JC-P＝8.9Hz),130.8(d,JC-P＝6.0Hz),130.6(d,JC-P ＝97.7Hz),130.3(d,JC-P＝99.1Hz),129.2,128.5(d,JC-P＝3.6Hz),128.5(d,JC-P＝20.1Hz),127.6(d,JC-P＝4.0Hz), 123.8(d,JC-P＝4.4Hz),120.2,119.9(d,JC-P＝1.0Hz),113.9, 55.2,52.8(d,JC-P＝65.6Hz)；31P NMR(162 MHz,CDCl3)δ38.4； IR(KBr):3425,3060,2958,1608,1510,1455,1438,1384,1249, 1154,1118,1031,831,784,754,561,529；HRMS(ESI)calcd for C26H24O3P[(M+H)]+:415.1458,found:415.1457。
Claims (5)
1.一种具有羟基苯基官能团的二芳基磷化合物，其特征在于：结构通式为：
所述R1为C1-C6的烷基；苯基及含有取代基的苯环，取代基为C1-C6的烷基、三氟甲基、甲氧基中的一种或几种；
所述R2为C1-C6的烷基；苯基及含有取代基的苯环，取代基为F、Cl、Br、Me、MeO中的一种或几种。
2.如权利要求1所述的具有羟基苯基官能团的二芳基磷化合物的制备方法，其特征在于：以酚类化合物和二苯基磷氧为反应物，按照如下反应制备：
所述R1为C1-C6的烷基；苯基及含有取代基的苯环，取代基为C1-C6的烷基、三氟甲基、甲氧基中的一种或几种；
所述R2为C1-C6的烷基；苯基及含有取代基的苯环，取代基为F、Cl、Br、Me、MeO的一种或几种；
具体反应步骤为：
将酚类化合物溶于浓度为0.01～1.0mol/L的有机溶剂中，向该体系按一定比例加入二苯基磷氧，然后向该反应混合物中按一定比例加入无机碱，在30～150℃下搅拌反应1～48小时，反应完毕后加水淬灭，静置分液，水层用二氯甲烷萃取2～8次，合并有机相，最后用无水硫酸钠干燥、过滤，减压除去溶剂后柱层析或重结晶得到具有羟基苯基官能团的二芳基磷化合物。
3.如权利要求2所述的具有羟基苯基官能团的二芳基磷化合物的制备方法，其特征在于，所述酚类化合物、二苯基磷氧与无机碱的摩尔比为1:(0.8～2.0):(0.8～2.0)。
4.如权利要求2所述的具有羟基苯基官能团的二芳基磷化合物的制备方法，其特征在于：所述有机溶剂为四氢呋喃、二氯甲烷、甲苯、1,4-二氧六环、苯中的一种或几种。
5.如权利要求2所述的具有羟基苯基官能团的二芳基磷化合物的制备方法，其特征在于：所述无机碱为促进剂，可以为碳酸钾、碳酸钠、碳酸铯、氢氧化钠、氢氧化钾、磷酸钠、磷酸钾中的一种或几种。
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| CN110903317A (zh) * | 2019-12-16 | 2020-03-24 | 西南大学 | 一种制备多取代偕二芳基甲基磷酸酯类化合物的方法 |
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| CN109096334B (zh) * | 2018-09-12 | 2021-01-15 | 广西大学 | 一种手性芳基膦氧化合物及其衍生物的制备方法 |
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