CN109678899B - 一种二芳基膦酰肼类化合物及其制备方法 - Google Patents
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- -1 Diaryl phosphine Chemical compound 0.000 title claims abstract description 37
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 150000001875 compounds Chemical class 0.000 title claims abstract description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims abstract description 7
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims abstract description 7
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 13
- 238000000034 method Methods 0.000 claims abstract description 10
- 239000002904 solvent Substances 0.000 claims abstract description 9
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 238000004519 manufacturing process Methods 0.000 claims abstract 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 11
- IICCLYANAQEHCI-UHFFFAOYSA-N 4,5,6,7-tetrachloro-3',6'-dihydroxy-2',4',5',7'-tetraiodospiro[2-benzofuran-3,9'-xanthene]-1-one Chemical group O1C(=O)C(C(=C(Cl)C(Cl)=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 IICCLYANAQEHCI-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 229930187593 rose bengal Natural products 0.000 claims description 7
- 229940081623 rose bengal Drugs 0.000 claims description 7
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 6
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 6
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 6
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 claims description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- 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 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 239000002994 raw material Substances 0.000 abstract description 3
- 238000001308 synthesis method Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 230000002194 synthesizing effect Effects 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 238000005580 one pot reaction Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000004440 column chromatography Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000012467 final product Substances 0.000 description 6
- 238000000926 separation method Methods 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- NRESDXFFSNBDGP-UHFFFAOYSA-N (4-bromophenyl)hydrazine Chemical group NNC1=CC=C(Br)C=C1 NRESDXFFSNBDGP-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- GPAYUJZHTULNBE-UHFFFAOYSA-N diphenylphosphine Chemical compound C=1C=CC=CC=1PC1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GPTOGZLZMLJZCV-UHFFFAOYSA-N (3-methylphenyl)hydrazine Chemical compound CC1=CC=CC(NN)=C1 GPTOGZLZMLJZCV-UHFFFAOYSA-N 0.000 description 1
- ZXBMIRYQUFQQNX-UHFFFAOYSA-N (4-fluorophenyl)hydrazine Chemical compound NNC1=CC=C(F)C=C1 ZXBMIRYQUFQQNX-UHFFFAOYSA-N 0.000 description 1
- XAMBIJWZVIZZOG-UHFFFAOYSA-N (4-methylphenyl)hydrazine Chemical compound CC1=CC=C(NN)C=C1 XAMBIJWZVIZZOG-UHFFFAOYSA-N 0.000 description 1
- 238000003383 Atherton-Todd reaction Methods 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- MDDUHVRJJAFRAU-YZNNVMRBSA-N tert-butyl-[(1r,3s,5z)-3-[tert-butyl(dimethyl)silyl]oxy-5-(2-diphenylphosphorylethylidene)-4-methylidenecyclohexyl]oxy-dimethylsilane Chemical compound C1[C@@H](O[Si](C)(C)C(C)(C)C)C[C@H](O[Si](C)(C)C(C)(C)C)C(=C)\C1=C/CP(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 MDDUHVRJJAFRAU-YZNNVMRBSA-N 0.000 description 1
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- 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/36—Amides thereof
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Abstract
本发明公开了一种二芳基膦酰肼类化合物及其制备方法,以有机染料为光敏剂,添加当量碱,将芳基肼、二芳基氧磷为反应物,乙腈为溶剂,温度控制在25‑45℃,在可见光照射下反应5‑9 h后,经过柱层析分离到产物二芳基膦酰肼类化合物。本发明首次提供了一种一步合成法,具体为以廉价易得的芳基肼和二芳基氧磷类化合物作为起始原料合成二芳基膦酰肼类目标化合物的新方法。该方法具有反应条件温和、操作方便等优势;在药物合成,两步法可能会导致最终的收率大打折扣且操作较为复杂,给药物生产和应用带来较大困扰,因此本发明中的一锅煮法催化体系展现了巨大的潜在应用价值。
Description
技术领域
本发明涉及化学合成领域,具体涉及一种二芳基膦酰肼类化合物的制备方法。
背景技术
膦酰肼类化合物在杀菌剂、生长调节剂、阻燃剂等方面具有很好的应用前景。经典的Atherton-Todd反应可以合成膦酰肼类化合物,但是其反应底物局限在二烷基氧膦和O,O-二烷基膦酸酯等,而二芳基氧膦无法发生反应合成二芳基膦酰肼类化合物。此外,膦酰肼类化合物还可以通过“两步法”进行合成,首先芳基肼类化合物和二氯化磷作用,分离得到第一步产物,接着该产物在氧化剂过氧化氢(Polyhedron 2003 (22), 1397–1405)或过量的碱碳酸钾(J. Am. Chem. Soc. 2008, 130, 5542–5551)作用发生氧化反应,最终分离得到膦酰肼类化合物。合成步骤较复杂,后处理过程较为繁琐。本发明中所公布的在可见光照射下以芳香肼类化合物和二芳基氧磷为原料一步反应直接合成二芳基膦酰肼类化合物的方法暂时没有相关文献及专利报道。
发明内容
本发明提出了一种二芳基膦酰肼类化合物的制备方法,提供一种温和、廉价、简单的可见光催化方法来合成二芳基膦酰肼类化合物。该合成方法反应条件温和,在可见光照条件下,简便安全,原料和催化剂价廉易得,是一种环境友好的绿色合成方法。
实现本发明的技术方案是:一种二芳基膦酰肼类化合物,结构式如下:
其中,R1为甲氧基、甲基、氟、氰基、氯、硝基。
所述的二芳基膦酰肼类化合物的制备方法,步骤如下:将芳香肼、二芳基氧磷和溶剂加入反应管中,随后向其中加入碱和光敏剂,在可见光照射下于空气中、搅拌条件下反应,得到二芳基膦酰肼类化合物。
所述芳香肼的结构式如下:
其中R1为甲氧基、甲基、氟、氰基、氯、硝基。
所述二芳基氧磷的结构式如下:
其中R2为乙基、正丁基、异丙基、苯基。
所述溶剂为乙腈或二甲基亚砜;碱为碳酸铯或者三乙烯二胺;光敏剂为孟加拉玫瑰红。
所述芳香肼、二芳基氧磷、碱和光敏剂的摩尔比为1.1:(1-2):1.0:0.1。
所述的反应温度为25-45 ℃,反应时间为5-9 h。
本发明所述制备方法的反应通式如下:
本发明的有益效果是:本发明提供了一种二芳基膦酰肼类化合物的制备方法,所述方法不需要进行两步操作,在可见光照射下使用廉价易得的光敏剂作催化剂来高效合成二芳基膦酰肼类化合物。该方法所涉及的操作简便安全、具有反应条件温和、经济性好、环境友好的优点。
具体实施方式
下面将结合本发明实施例,对本发明的技术方案进行清楚、完整地描述,显然,所描述的实施例仅仅是本发明一部分实施例,而不是全部的实施例。基于本发明中的实施例,本领域普通技术人员在没有付出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
实施例1
二芳基膦酰肼类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂孟加拉玫瑰红 (10 mol%),碳酸铯 (1 equiv.),溶剂乙腈1.5 mL、苯肼0.55 mmol,二苯基氧磷1.0 mmol,于空气中搅拌控制反应温度为45℃,于白光照射下反应9小时后,硅胶柱层析分离得到最终产物,以二苯基氧磷摩尔量为100%计,终产物的产率为55 %。
具体结果如下:
1H NMR (DMSO, 400 MHz)δ = 7.87-7.94 (m, 4H), 7.60 – 7.36 (m, 8H),7.14 (m, 2H), 7.08 – 6.96 (m, 2H), 6.76 – 6.63 (t, 1H); 13C NMR(CDCl3, 100MHz): (101 MHz, δ =150.84 (d, J = 5.2 Hz), 133.72, 132.73 – 132.24 (m),132.05 (d, J = 2.5 Hz), 129.89 – 127.07 (m), 118.83, 113.41。
实施例2
二芳基膦酰肼类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂孟加拉玫瑰红 (10 mol%),碳酸铯 (1 equiv),溶剂乙腈1.5 mL、4-甲基苯肼0.55 mmol,二苯基氧磷1.0 mmol,搅拌控制反应温度为45 ℃,于白光照射下反应9小时后,硅胶柱层析分离得到最终产物。
具体结果如下:
1H NMR (CDCl3,400 MHz) δ = 7.98 (ddt, J = 11.9, 7.0, 1.5 Hz, 4H), 7.59– 7.50 (m, 2H), 7.46 (ddd, J = 7.0, 5.6, 2.6 Hz, 4H), 7.04 (d, J = 8.2 Hz,2H), 6.96 – 6.88 (m, 2H), 5.78 (d, J = 2.7 Hz, 1H), 5.04 (d, J = 16.7 Hz,1H), 2.28 (s, 3H); 13C NMR (CDCl3, 101 MHz) δ = 146.12 (d, J = 7.0 Hz), 131.72(d, J = 104 Hz), 132.15 (d, J = 9.6 Hz), 129.92, 129.60, 128.59 (d, J = 12.5Hz), 113.54, 58.45。
实施例3
二芳基膦酰肼类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂孟加拉玫瑰红 (10 mol%),碳酸铯 (1 equiv),溶剂二甲基亚砜1.5 mL、3-甲基苯肼0.5 mmol,二苯氧磷1.0 mmol,于空气中搅拌控制反应温度为35 ℃,于白光照射下反应2小时后,硅胶柱层析分离得到最终产物。
具体结果如下:
1H NMR (DMSO-d6, 400 MHz) δ = 7.91 (ddt, J = 11.5, 6.6, 1.6 Hz, 4H),7.64 – 7.43 (m, 6H), 7.45 – 7.32 (m, 2H), 7.02 (t, J = 7.7 Hz, 1H), 6.89 –6.77 (m, 2H), 6.51 (d, J = 7.3 Hz, 1H), 2.22 (s, 3H); 13C NMR (DMSO-d6, 101MHz) δ = 150.84 (d, J = 5.2 Hz), 137.84, 133.75, 132.45 (d, J = 8.5 Hz),132.04, 128.84 (d, J = 12.3 Hz), 119.73, 113.99, 110.71, 21.84。
实施例4
芳基膦酸酯类化合物的制备方法,步骤如下:
在25 mL反应管中加入光敏剂孟加拉玫瑰红 (10 mol%),碳酸铯 (1 equiv),溶剂二甲基亚砜1.5 mL、4-氟苯肼0.55 mmol,二苯氧磷1.0 mmol,搅拌并控制反应温度为35℃,于白光照射下反应8小时后,硅胶柱层析分离得到最终产物。
具体结果如下:
1H NMR ((CD3)2SO, 400 MHz) δ = 7.90 (ddt, J = 11.5, 6.6, 1.6 Hz, 4H),7.62 – 7.37 (m, 8H), 7.11 – 6.84 (m, 4H);13C NMR ((CD3)2SO, 101 MHz) δ =156.23 (d, J = 233 Hz), 147.43, 133.66, 132.43 (d, J = 9.2 Hz), 132.09 (d, J= 2.9 Hz), 128.87 (d, J = 12.3 Hz), 115.27 (d, J = 22.0 Hz), 114.56 (d, J =7.4 Hz)。
实施例5
二芳基膦酰肼类化合物的制备方法,步骤如下:
芳香肼为4-溴苯肼,在25 mL反应管中加入光敏剂孟加拉玫瑰红 (10 mol%),三乙烯二胺 (1 equiv),溶剂乙腈1.5 mL、4-溴苯肼0.55 mmol,二苯基氧磷0.8 mmol,于空气中搅拌控制反应温度为45 ℃,于白光照射下反应5小时后,硅胶柱层析分离得到最终产物。
具体结果如下:
1H NMR ((CD3)2SO, 400 MHz) δ = 7.96 – 7.82 (m, 4H), 7.71 (d, J = 3.4Hz, 1H), 7.62 – 7.46 (m, 7H), 7.28 (d, J = 8.8 Hz, 2H), 6.98 (d, J = 8.9 Hz,2H);13C NMR ((CD3)2SO, 101 MHz) δ = 150.25 (d, J = 5.1 Hz), 133.47, 132.43 (d,J = 9.0 Hz), 132.18 (d, J = 3.3 Hz), 131.46, 128.90 (d, J = 12.0 Hz), 115.36,109.57。
以上所述仅为本发明的较佳实施例而已,并不用以限制本发明,凡在本发明的精神和原则之内,所作的任何修改、等同替换、改进等,均应包含在本发明的保护范围之内。
Claims (4)
2.根据权利要求1所述的二芳基膦酰肼类化合物的制备方法,其特征在于:所述溶剂为乙腈、二甲基亚砜中的一种;碱为碳酸铯、三乙烯二胺中的一种;光敏剂为孟加拉玫瑰红。
3.根据权利要求1所述的二芳基膦酰肼类化合物的制备方法,其特征在于:所述芳香肼、二苯基氧磷、碱和光敏剂的摩尔比为1:(1-2):0.5:0.05。
4.根据权利要求1所述的二芳基膦酰肼类化合物的制备方法,其特征在于:所述的反应温度为25-45℃,反应时间为5-9h。
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CN108530481A (zh) * | 2017-11-09 | 2018-09-14 | 广西大学 | 一种吲哚酮膦酰肼化合物及其衍生物的制备方法 |
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