CN109678899A - A kind of diaryl phosphin hydrazide kind compound and preparation method thereof - Google Patents
A kind of diaryl phosphin hydrazide kind compound and preparation method thereof Download PDFInfo
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- CN109678899A CN109678899A CN201910040029.5A CN201910040029A CN109678899A CN 109678899 A CN109678899 A CN 109678899A CN 201910040029 A CN201910040029 A CN 201910040029A CN 109678899 A CN109678899 A CN 109678899A
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- diarylphosphonium
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- hydrazide
- follows
- hydrazide compound
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- -1 diaryl phosphin Chemical compound 0.000 title claims description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 13
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 6
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical group [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 6
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 6
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 239000002585 base Substances 0.000 claims description 4
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- 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
- 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
- 125000003118 aryl group Chemical group 0.000 claims 3
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 abstract description 6
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 230000003197 catalytic effect Effects 0.000 abstract description 2
- 238000001308 synthesis method Methods 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract 2
- 229940079593 drug Drugs 0.000 abstract 2
- 238000004440 column chromatography Methods 0.000 abstract 1
- 238000010411 cooking Methods 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 238000005580 one pot reaction Methods 0.000 abstract 1
- 239000000376 reactant Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 240000008254 Rosa chinensis Species 0.000 description 5
- 235000000664 Rosa chinensis Nutrition 0.000 description 5
- AZJPTIGZZTZIDR-UHFFFAOYSA-L rose bengal Chemical compound [K+].[K+].[O-]C(=O)C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 AZJPTIGZZTZIDR-UHFFFAOYSA-L 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
- IFOOABKNGLKLLE-UHFFFAOYSA-N OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.O Chemical compound OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.OP(OC1=CC=CC=C1)(OC1=CC=CC=C1)=O.O IFOOABKNGLKLLE-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 3
- NRESDXFFSNBDGP-UHFFFAOYSA-N (4-bromophenyl)hydrazine Chemical group NNC1=CC=C(Br)C=C1 NRESDXFFSNBDGP-UHFFFAOYSA-N 0.000 description 2
- OTEKOJQFKOIXMU-UHFFFAOYSA-N 1,4-bis(trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=C(C(Cl)(Cl)Cl)C=C1 OTEKOJQFKOIXMU-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- AFCIMSXHQSIHQW-UHFFFAOYSA-N [O].[P] Chemical compound [O].[P] AFCIMSXHQSIHQW-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000003760 hair shine Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229960000624 procarbazine Drugs 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000003383 Atherton-Todd reaction Methods 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000758 substrate Substances 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
- C07F9/30—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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- 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)
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。The invention discloses a diarylphosphonium hydrazide compound and a preparation method thereof. An organic dye is used as a photosensitizer, an equivalent base is added, arylhydrazine and diarylphosphorus oxide are used as reactants, acetonitrile is used as a solvent, and the temperature is controlled After reacting for 5-9 h under visible light irradiation at 25-45 °C, the product diarylphosphonium hydrazide compounds were isolated by column chromatography. The present invention provides a one-step synthesis method for the first time, specifically a new method for synthesizing the target compound of diarylphosphonium hydrazide by using cheap and easily available arylhydrazine and diaryloxophosphorus compound as starting materials. The method has the advantages of mild reaction conditions and convenient operation; in the synthesis of drugs, the two-step method may lead to a large reduction in the final yield and the operation is relatively complicated, which brings great trouble to the production and application of drugs. Therefore, the one-pot cooking method in the present invention The catalytic system shows great potential application value.
Description
Technical field
The present invention relates to the field of chemical synthesis, and in particular to a kind of preparation method of diaryl phosphin hydrazide kind compound.
Background technique
Phosphono hydrazine class compound fungicide, growth regulator, in terms of have a good application prospect.It is classical
Atherton-Todd reaction can synthesize phosphono hydrazine class compound, but its reaction substrate is confined to dialkyl group phosphine oxide and O,
O- dialkyl phosphonate etc., the synthesis of diaryl phosphono hydrazine class compound and diaryl phosphine oxide can not react.In addition, phosphono hydrazine
Class compound can also be synthesized by " two-step method ", first aryl hydrazine class compound and phosphorus dichloride effect, isolated
First step product, then the product is in oxidants hydrogen peroxide (Polyhedron 2003 (22), 1397-1405) or excess
Alkali potassium carbonate (J. Am. Chem. Soc. 2008,130,5542-5551) effect occur oxidation reaction, be finally recovered
To phosphono hydrazine class compound.Synthesis step is more complex, and last handling process is relatively complicated.That is announced in the present invention shines in visible light
It penetrates down using fragrant hydrazine class compound and diaryl oxygen phosphorus as the direct synthesis of diaryl phosphono hydrazine class compound of raw material single step reaction
Method is temporarily without pertinent literature and patent report.
Summary of the invention
The invention proposes a kind of preparation methods of diaryl phosphin hydrazide kind compound, provide a kind of mild, cheap, simple
Visible light catalytic method carry out synthesis of diaryl phosphono hydrazine class compound.The synthesising method reacting condition is mild, shines in visible light
Under the conditions of, handy and safe, raw material and catalyst are cheap and easy to get, are a kind of environmental-friendly green synthesis methods.
It realizes the technical scheme is that a kind of diaryl phosphin hydrazide kind compound, structural formula are as follows:
Wherein, R1For methoxyl group, methyl, fluorine, cyano, chlorine, nitro.
The preparation method of the diaryl phosphin hydrazide kind compound, steps are as follows: by aryl hydrazine, diaryl oxygen phosphorus and molten
Agent is added in reaction tube, and alkali and photosensitizer are then added thereto, anti-in air, under stirring condition under visible light illumination
It answers, obtains diaryl phosphin hydrazide kind compound.
The structural formula of the aryl hydrazine is as follows:
Wherein R1For methoxyl group, methyl, fluorine, cyano, chlorine, nitro.
The structural formula of the diaryl oxygen phosphorus is as follows:
Wherein R2For ethyl, normal-butyl, isopropyl, phenyl.
The solvent is acetonitrile or dimethyl sulfoxide；Alkali is cesium carbonate or triethylene diamine；Photosensitizer is Bangladesh's rose
It is rare red.
The aryl hydrazine, diaryl oxygen phosphorus, alkali and photosensitizer molar ratio be 1.1:(1-2): 1.0:0.1.
The reaction temperature is 25-45 DEG C, and the reaction time is 5-9 h.
The reaction formula of preparation method of the present invention is as follows:
The beneficial effects of the present invention are: the present invention provides a kind of preparation method of diaryl phosphin hydrazide kind compound, the side
Method does not need to carry out two step operations, and two virtues are efficiently synthesized as catalyst using photosensitizer cheap and easy to get under visible light illumination
Base phosphono hydrazine class compound.Easy to operate and safe involved in this method, mild with reaction condition, good economy performance, environment friend
Good advantage.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical solution of the present invention is clearly and completely described, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
Those of ordinary skill in the art's every other embodiment obtained under that premise of not paying creative labor, belongs to this hair
The range of bright protection.
Embodiment 1
The preparation method of diaryl phosphin hydrazide kind compound, steps are as follows:
Photosensitizer Bengal rose red (10 mol%) is added in 25 mL reaction tubes, cesium carbonate (1 equiv.), solvent second
1.5 mL of nitrile, 0.55 mmol of phenylhydrazine, 1.0 mmol of diphenyl phosphate oxygen, mixing control reaction temperature is 45 DEG C in air, in
After being reacted 9 hours under white light, the isolated final product of silica gel column chromatography, by diphenyl phosphate oxygen mole be 100 % in terms of,
The yield of final product is 55 %.
Concrete outcome is as follows:
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, 100 MHz):
(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。
Embodiment 2
The preparation method of diaryl phosphin hydrazide kind compound, steps are as follows:
Photosensitizer Bengal rose red (10 mol%) is added in 25 mL reaction tubes, cesium carbonate (1 equiv), solvent acetonitrile
1.5 mL, 4- procarbazine, 0.55 mmol, 1.0 mmol of diphenyl phosphate oxygen, mixing control reaction temperature are 45 DEG C, Yu Baiguang
After lower reaction 9 hours of irradiation, the isolated final product of silica gel column chromatography.
Concrete outcome is as follows:
1H NMR (CDCl3, 400 MHz) and 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 = 12.5 Hz),
113.54, 58.45。
Embodiment 3
The preparation method of diaryl phosphin hydrazide kind compound, steps are as follows:
Photosensitizer Bengal rose red (10 mol%) is added in 25 mL reaction tubes, cesium carbonate (1 equiv), solvent diformazan
1.5 mL, 3- procarbazine of base sulfoxide, 0.5 mmol, 1.0 mmol of hexichol oxygen phosphorus, mixing control reaction temperature is 35 in air
DEG C, after being reacted 2 hours under white light, the isolated final product of silica gel column chromatography.
Concrete outcome is as follows:
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, 101 MHz) 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。
Embodiment 4
The preparation method of arylphosphonic acid ester type compound, steps are as follows:
Photosensitizer Bengal rose red (10 mol%) is added in 25 mL reaction tubes, cesium carbonate (1 equiv), solvent diformazan
1.5 mL, 4- fluorine phenylhydrazine of base sulfoxide, 0.55 mmol, 1.0 mmol of hexichol oxygen phosphorus, stirring and controlling reaction temperature is 35 DEG C, in
After being reacted 8 hours under white light, the isolated final product of silica gel column chromatography.
Concrete outcome is as follows:
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)。
Embodiment 5
The preparation method of diaryl phosphin hydrazide kind compound, steps are as follows:
Aryl hydrazine is 4- bromophenyl-hydrazine, photosensitizer Bengal rose red (10 mol%) is added in 25 mL reaction tubes, triethylene two
Amine (1 equiv), 1.5 mL, 4- bromophenyl-hydrazine of solvent acetonitrile 0.55 mmol, 0.8 mmol of diphenyl phosphate oxygen are stirred in air
Controlling reaction temperature is 45 DEG C, after reacting 5 hours under white light, the isolated final product of silica gel column chromatography.
Concrete outcome is as follows:
1H NMR ((CD3)2SO, 400 MHz) δ = 7.96 – 7.82 (m, 4H), 7.71 (d, J = 3.4 Hz,
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。
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the invention, all in essence of the invention
Within mind and principle, any modification, equivalent replacement, improvement and so on be should all be included in the protection scope of the present invention.
Claims (8)
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103025812A (en) * | 2010-07-28 | 2013-04-03 | 巴斯夫欧洲公司 | Phosphinic acid hydrazide flame retardant compositions |
| CN108530481A (en) * | 2017-11-09 | 2018-09-14 | 广西大学 | A kind of preparation method of indolone phosphono hydrazine compound and its derivative |
-
2019
- 2019-01-16 CN CN201910040029.5A patent/CN109678899B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103025812A (en) * | 2010-07-28 | 2013-04-03 | 巴斯夫欧洲公司 | Phosphinic acid hydrazide flame retardant compositions |
| CN108530481A (en) * | 2017-11-09 | 2018-09-14 | 广西大学 | A kind of preparation method of indolone phosphono hydrazine compound and its derivative |
Non-Patent Citations (3)
| Title |
|---|
| E. BAYER ET AL.: "Mechanism of the "Hydrazinphenylhydrazinee Effect" Caused by N"-acyl-Nphenylhydrazine", 《THE JOURNAL OF PHOTOGRAPHIC SCIENCE》 * |
| HANS BOCK ET AL.: "Substituenten-Effekte bei Phenylazo-phosphorsaure-Derivaten", 《AZO-VERBINDUNGEN》 * |
| RAGAM RAJU ET AL.: "Copper(I)-Induced Sulfenylation of H-Phosphonates, H-Phosphonites and Phosphine Oxides with Aryl/alkylsulfonylhydrazides as a Thiol Surrogate", 《ADV. SYNTH. CATAL.》 * |
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