CN110256492A - One kind compound containing phosphine carboxylic acid and preparation method thereof - Google Patents
One kind compound containing phosphine carboxylic acid and preparation method thereof Download PDFInfo
- Publication number
- CN110256492A CN110256492A CN201910599890.5A CN201910599890A CN110256492A CN 110256492 A CN110256492 A CN 110256492A CN 201910599890 A CN201910599890 A CN 201910599890A CN 110256492 A CN110256492 A CN 110256492A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- aromatic radical
- reaction
- compound
- hydrogen
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 phosphine carboxylic acid Chemical class 0.000 title claims abstract description 45
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Natural products P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 150000001875 compounds Chemical class 0.000 title claims abstract description 32
- 229910000073 phosphorus hydride Inorganic materials 0.000 title claims abstract description 25
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 43
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000001569 carbon dioxide Substances 0.000 claims abstract description 18
- 229910002092 carbon dioxide Inorganic materials 0.000 claims abstract description 18
- 239000000758 substrate Substances 0.000 claims abstract description 11
- 239000003054 catalyst Substances 0.000 claims abstract description 9
- 238000005286 illumination Methods 0.000 claims abstract description 8
- 239000003513 alkali Substances 0.000 claims abstract description 7
- 238000004090 dissolution Methods 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 44
- 125000001072 heteroaryl group Chemical group 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 17
- 239000000126 substance Substances 0.000 claims description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 10
- 238000006467 substitution reaction Methods 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 239000002585 base Substances 0.000 claims description 8
- 239000000047 product Substances 0.000 claims description 7
- PRWATGACIORDEL-UHFFFAOYSA-N 2,4,5,6-tetra(carbazol-9-yl)benzene-1,3-dicarbonitrile Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=C(C#N)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C(N2C3=CC=CC=C3C3=CC=CC=C32)C(N2C3=CC=CC=C3C3=CC=CC=C32)=C1C#N PRWATGACIORDEL-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 230000000996 additive effect Effects 0.000 claims description 6
- 239000012074 organic phase Substances 0.000 claims description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims description 5
- 229910000024 caesium carbonate Inorganic materials 0.000 claims description 5
- 239000003480 eluent Substances 0.000 claims description 5
- TXNLQUKVUJITMX-UHFFFAOYSA-N 4-tert-butyl-2-(4-tert-butylpyridin-2-yl)pyridine Chemical compound CC(C)(C)C1=CC=NC(C=2N=CC=C(C=2)C(C)(C)C)=C1 TXNLQUKVUJITMX-UHFFFAOYSA-N 0.000 claims description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 claims description 4
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000003208 petroleum Substances 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 125000005610 enamide group Chemical group 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229960000583 acetic acid Drugs 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000012362 glacial acetic acid Substances 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 230000000171 quenching effect Effects 0.000 claims description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
- 238000004440 column chromatography Methods 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- 238000004679 31P NMR spectroscopy Methods 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- 229910000831 Steel Inorganic materials 0.000 description 4
- GCNLQHANGFOQKY-UHFFFAOYSA-N [C+4].[O-2].[O-2].[Ti+4] Chemical compound [C+4].[O-2].[O-2].[Ti+4] GCNLQHANGFOQKY-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000012295 chemical reaction liquid Substances 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 3
- 238000003818 flash chromatography Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical class COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 2
- 238000001514 detection method Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000003205 fragrance Substances 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000003107 substituted aryl group Chemical group 0.000 description 2
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- SULWMEGSVQCTSK-UHFFFAOYSA-N diethyl hydrogen phosphite Chemical class CCOP(O)OCC SULWMEGSVQCTSK-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 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 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 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
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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4056—Esters of arylalkanephosphonic acids
-
- 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
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4075—Esters with hydroxyalkyl compounds
-
- 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
- C07F9/5325—Aromatic phosphine oxides or thioxides (P-C aromatic linkage)
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/572—Five-membered rings
- C07F9/5728—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
-
- 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
-
- 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
- C07F9/6552—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 six-membered ring
-
- 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
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
-
- 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
- C07F9/6553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms
- C07F9/655345—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring
- C07F9/655354—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having sulfur atoms, with or without selenium or tellurium atoms, as the only ring hetero atoms the sulfur atom being part of a five-membered ring condensed with carbocyclic rings or carbocyclic ring systems
-
- 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
- C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
- C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
- C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
- C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
Landscapes
- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of compounds containing phosphine carboxylic acid and preparation method thereof.Preparation method includes the following steps: by reaction substrate and phosphine oxide compound and alkali mixed dissolution, photochemical catalyst is then added in carbon dioxide atmosphere, then in 10~60 DEG C, 1~100W illumination reaction 2~for 24 hours.Reaction condition of the present invention is mild, and reaction substrate is selectively wide, and is amplified to gram-grade scale, and yield is substantially unaffected.
Description
Technical field
The invention belongs to convert dioxy compound in the synthesis field of carboxylic acid, and in particular to a kind of compound containing phosphine carboxylic acid
And preparation method thereof.
Background technique
It is well known that carboxylic acid compound is widely present in drug molecule and natural products, not only in organic synthesis
It is widely applied, and there is extensive physiological activity.It is introduced in carboxylic acid compound and contains phosphine groups, phosphorus atoms can be utilized
The function of special property regulation carboxylic acid compound, particularly leads in researchs such as biochemistry, pharmaceutical chemistry and organic chemistry
Domain has a wide range of applications a-amino acid containing phosphine.There are synthetic route length, reaction item for the method for traditional synthesis amino acid containing phosphine
The disadvantages of part harshness and raw material are not easy to obtain, to limit the extensive use of these methods.
A kind of method containing phosphine carboxylic acid, the especially a-amino acid containing phosphine that can overcome disadvantages mentioned above how is developed as a result,
It is that this field is needed.
Summary of the invention
For above-mentioned deficiency in the prior art, the present invention provides one kind compound containing phosphine carboxylic acid and preparation method thereof, can
Effectively solve the problems, such as the existing route of compound synthesis containing phosphine carboxylic acid length, severe reaction conditions.
To achieve the above object, the technical solution adopted by the present invention to solve the technical problems is:
A kind of compound containing phosphine carboxylic acid, general formula of the chemical structure are as follows:
Wherein, X is aromatic radical, with any one of aromatic radical, alkyl or alkoxy replaced；A is hydrogen, alkyl, amine
Base, with protection amino, aryl, heteroaryl, band substitution aromatic radical or with any in substituted heteroaryl, ester group or hydroxyl
Kind；B be hydrogen, alkyl, amido, band protection amino, aryl, heteroaryl, with substitution aromatic radical or with substituted heteroaryl, ester
Any one of base or hydroxyl；C is hydrogen or alkyl.
Further, chemical structural formula is
Wherein, X is aromatic radical, with aromatic radical, alkyl or the alkoxy replaced；
R1For aromatic radical, with the aromatic radical replaced or with substituted heteroaryl；R2For aromatic radical, the aromatic radical with replacing, band
Any one in substituted heteroaryl, alkyl；R3For any one in hydrogen, alkyl or branched alkyl；
R4For aromatic radical, with the aromatic radical replaced or with any one in substituted heteroaryl；R5For hydrogen, alkyl or take
Any one in substituted alkyl；R6For any one in hydrogen, alkyl or branched alkyl；
R7For aromatic radical, with the aromatic radical replaced or with any one in substituted heteroaryl；R8For hydrogen, alkyl or take
Any one in substituted alkyl；
R9For any one in the alkyl of hydrogen, alkyl, branched alkyl or hetero atom substitution；R10For aryl, heteroaryl or
Substituted aryl, heteroaryl, any one in alkyl.
Further, the chemical structural formula for containing phosphine carboxylic acid compound are as follows:
The method for preparing the above-mentioned compound containing phosphine carboxylic acid, comprising the following steps:
By reaction substrate and phosphine oxide compound and alkali mixed dissolution, photochemical catalyst then is added in carbon dioxide atmosphere,
Then in 10~60 DEG C, 1~100W illumination reaction 2~for 24 hours；
Wherein, the additive amount of phosphine oxide compound is 1~3 times of the amount of reaction substrate substance；The additive amount of alkali is reaction bottom
1~20 times of the amount of object substance；The additive amount of photochemical catalyst is the 0.1~5% of the amount of reaction substrate substance；
Reaction substrate is enamides, olefin(e) compound, enol silyl ether compound or acrylic ester compound.
Further, enamides structural formula are as follows:Wherein, R1For aromatic radical, with the fragrance replaced
Base or heteroaryl；R2For aromatic radical, with any one in the aromatic radical replaced, the heteroaryl with substitution, alkyl；R3For hydrogen, alkane
Any one in base or branched alkyl.
Further, olefin(e) compound structural formula are as follows:Wherein, R4For aromatic radical, with the fragrance replaced
Any one in base or heteroaryl；R5For any one in hydrogen, alkyl or substitution alkyl；R6For hydrogen, alkyl or branched alkyl
In any one.
Further, the structural formula of enol silyl ether compound are as follows:Wherein, R7For aromatic radical, with what is replaced
Any one in aromatic radical or heteroaryl；R8For any one in hydrogen, alkyl or substitution alkyl.
Further, acrylic ester compoundWherein, R9For hydrogen, alkyl, branched alkyl or miscellaneous original
Son replace alkyl in any one；R10It is any one in aryl, heteroaryl or substituted aryl, heteroaryl or alkyl
Kind.
Further, phosphine oxide compound is aryl phosphine oxide compound, phosphonate ester compound or alkyl phosphine oxide compound.
Further, phosphine oxide compound is diaryl phosphine oxide, phosphorous acid dialkoxy base ester or dialkyl group phosphine oxide.
Further, alkali is lithium carbonate, sodium carbonate or cesium carbonate.
Further, photochemical catalyst 4CzIPN, Ir [(ppy)2(dtbppy)]PF6、Ir[(ppy)2(dtbppy)]
PF6Ir[dF(CF3)ppy]2(dtbbpy)PF6Or Ir [dF (Me) ppy]2(dtbbpy)PF6。
Further, reaction condition are as follows: in carbon dioxide atmosphere, in 20~25 DEG C, 30~35W illumination reaction 10~
12h。
Further, the light source used when illumination reaction is blue light.
Further, further includes: after reaction, with sour quenching reaction product, then it is extracted with ethyl acetate at least 5 times,
And the organic phase extracted every time is merged and is concentrated, then column chromatographic purifying is carried out to enriched product.
Further, acid is hydrochloric acid.
Further, the eluant, eluent used when column chromatographs is the methylene chloride-methanol mixing that volume ratio is 100:1~20:1
The petroleum ether-ethyl acetate mixed liquor that liquid or volume ratio are 2:1~1:1, and the methylene chloride-methanol mixed liquor and petroleum
The promising glacial acetic acid for accounting for its total volume 0.1~0.6% is added in ether-ethyl acetate mixtures.
The invention has the benefit that
1, photoinduction can efficiently synthesized the carboxylic acid compound containing phosphine in the presence of photochemical catalyst, together by the present invention
When, the invention also includes the methods of efficient a-amino acid of the synthesis containing phosphine, the 'alpha '-hydroxy acids containing phosphine.
2, reaction condition of the present invention is mild, and reaction substrate is selectively wide, and is amplified to gram-grade scale, and yield is not substantially by shadow
It rings；Prior art reaction route length, the defect of severe reaction conditions are overcome simultaneously, and there is good prospects for commercial application.
Specific embodiment
A specific embodiment of the invention is described below, in order to facilitate understanding by those skilled in the art this hair
It is bright, it should be apparent that the present invention is not limited to the ranges of specific embodiment, for those skilled in the art,
As long as various change is in the spirit and scope of the present invention that the attached claims limit and determine, these variations are aobvious and easy
See, all are using the innovation and creation of present inventive concept in the column of protection.
Embodiment 1
A kind of compound containing phosphine carboxylic acid, chemical structural formula are as follows:
Its reactional equation are as follows:
The compound the preparation method is as follows:
(1) 45mg is added in dry 10mL Shrek pipe, 0.2mmol acrylamide (1a) then shifts reaction tube
Into glove box, 49mg, 0.24mmol diphenyl phosphine oxide (2a) and 41mg, 0.3mmol potassium carbonate are added；
(2) reaction tube is taken out and is connected afterwards with the biexhaust pipe for being connected with carbon dioxide steel cylinder, taken out on biexhaust pipe and fill titanium dioxide
Carbon 3 times, the nitrogen in drain makes that 2mL DMF is then added under carbon dioxide atmosphere full of carbon dioxide gas in its pipe
With photosensitizer 4CzIPN (32 μ L, 0.1mol%, 5mg are dissolved in 1mL DMF)；
(3) finally, placing reaction liquid into away from 30W blue LED lamp 2-3cm, stirring 12 hours under room temperature (25 DEG C), so
4.5mL water and 0.5mL 2N hydrochloric acid mixture are used afterwards, then are extracted with ethyl acetate reaction mixture at least 5 times, it will be each
Directly concentration is spin-dried for after the organic phase being obtained by extraction merges.Residue passes through flash column chromatography (eluant, eluent CH2Cl2/
MeOH 100/1~20/1: contain 0.2%AcOH) obtain pure required product, yield 89%.
The product is white solid, nuclear magnetic data are as follows:1H NMR(400MHz,DMSO-d6)δ13.36(s,1H),8.48
(s,1H),7.90–7.79(m,2H),7.68–7.59(m,2H),7.58–7.43(m,8H),7.42–7.35(m,2H),7.29–
7.13 (m, 6H), 4.16 (dd, J=15.0,6.6Hz, 1H), 3.68-3.58 (m, 1H)13C NMR(101MHz,DMSO-d6)δ
172.85 (d, J=5.6Hz), 164.94,140.16 (d, J=9.1Hz), 135.72 (d, J=98.9Hz), 133.90,
133.17 (d, J=99.0Hz), 132.04 (d, J=2.6Hz), 131.88,131.29 (d, J=2.9Hz), 130.78 (d, J=
9.5Hz), 130.40 (d, J=9.3Hz), 129.13 (d, J=11.5Hz), 128.65,128.36 (d, J=11.8Hz),
(128.34,127.70,127.01,126.44,62.58 d, J=5.0Hz), 34.10 (d, J=70.9Hz)31P NMR
(162MHz,DMSO-d6)δ26.92.HRMS(ESI+):calculated m/z[M+H]+for[C28H24NO4PH]+:
470.1516,found:470.1513.
Embodiment 2
A kind of compound containing phosphine carboxylic acid, chemical structural formula are as follows:
Its reactional equation are as follows:
The compound the preparation method comprises the following steps:
(1) it is added 45mg in 10mL dry Shrek pipe, 0.2mmol acrylamide (1a) and 4CzIPN (4mg,
2mol%), then reaction tube is transferred in glove box, adds 98mg, 0.3mmol cesium carbonate；
(2) reaction tube is taken out and is connected afterwards with the biexhaust pipe for being connected with carbon dioxide steel cylinder, taken out on biexhaust pipe and fill titanium dioxide
Carbon 3 times, the nitrogen in drain makes that 2mL DMF is then added under carbon dioxide atmosphere full of carbon dioxide gas in its pipe
With 31 μ L, 0.24mmol diethyl phosphites (2g)；
(3) finally, placing reaction liquid into away from 30W blue LED lamp 2-3cm, stirring 12 hours under room temperature (25 DEG C), so
5mL water is added afterwards, then at least 3 times removing impurity are extracted with ethyl acetate, 0.5mL 2N hydrochloric acid is then added, then use organic solvent
Ethyl acetate extracts at least 4 times, and the organic phase being obtained by extraction directly is concentrated after merging, and obtains pure target product, yield 78%.
The compound is white solid, nuclear magnetic data are as follows:1H NMR(400MHz,DMSO-d6)δ13.59(s,1H),
8.24(s,1H),7.86–7.77(m,2H),7.61–7.56(m,1H),7.56–7.45(m,4H),7.38–7.31(m,2H),
7.32-7.26 (m, 1H), 4.00-3.89 (m, 2H), 3.86-3.70 (m, 2H), 3.44-3.33 (m, 2H), 3.15 (dd, J=
18.7,15.2Hz, 1H), 1.13 (t, J=7.0Hz, 3H), 0.97 (t, J=7.0Hz, 3H)13C NMR(101MHz,DMSO-
d6) δ 172.82 (d, J=6.0Hz), 165.38,140.40 (d, J=13.7Hz), 134.65,132.09,129.07,
(128.63,127.89,127.33,126.23 d, J=1.4Hz), 61.85 (d, J=4.6Hz), 61.65 (d, J=6.1Hz),
61.51 (d, J=6.7Hz), 30.12 (d, J=139.8Hz), 16.47 (d, J=6.1Hz), 16.26 (d, J=6.2Hz)31P
NMR(162MHz,DMSO-d6)δ26.28.HRMS(ESI+):calculated m/z[M+H]+for[C20H24NO6PH]+:
406.1414,found:406.1413.
Embodiment 3
A kind of compound containing phosphine carboxylic acid, chemical structural formula are as follows:
Its reactional equation are as follows:
The compound the preparation method comprises the following steps:
(1) 1mg, 0.5mol%4CzIPN is added in 10mL dry Shrek pipe, reaction tube is then transferred to hand
49mg, 0.24mmol diphenyl phosphine oxide (2a) and 98mg, 0.3mmol cesium carbonate are added in casing；
(2) reaction tube is taken out and is connected afterwards with the biexhaust pipe for being connected with carbon dioxide steel cylinder, taken out on biexhaust pipe and fill titanium dioxide
Carbon 3 times, the nitrogen in drain makes that 2mL DMF is then added under carbon dioxide atmosphere full of carbon dioxide gas in its pipe
With 23 μ L, 0.2mmol styrene (8a)；
(3) finally, placing reaction liquid into away from 30W blue LED lamp 2-3cm, stirring 12 hours under room temperature (25 DEG C), so
4.5mL water and 0.5mL 2N hydrochloric acid mixture are used afterwards, then is extracted with ethyl acetate reaction mixture at least 3 times, are extracted
To organic phase merge after directly concentration be spin-dried for.Residue (eluant, eluent PE/EA 2/1~1/1: is contained by flash column chromatography
0.2-0.6%AcOH) obtain pure required product, yield 81%.
The compound is white solid, and nuclear magnetic data is as follows:1H NMR(400MHz,DMSO-d6)δ12.50(s,1H),
7.87–7.77(m,2H),7.77–7.66(m,2H),7.59–7.45(m,4H),7.45–7.37(m,2H),7.29–7.12(m,
5H),3.90–3.74(m,1H),3.29–3.14(m,1H),2.97–2.79(m,1H).13C NMR(101MHz,DMSO-d6)δ
173.90 (d, J=6.7Hz), 139.68 (d, J=9.3Hz), 134.53 (d, J=97.7Hz), 133.80 (d, J=
97.0Hz), 132.04 (d, J=2.7Hz), 131.82 (d, J=2.7Hz), 130.90 (d, J=9.0Hz), 130.82 (d, J=
9.1Hz), 129.00 (d, J=11.5Hz), 128.87 (d, J=11.4Hz), 128.84,128.19,127.58,45.10 (d, J
=2.1Hz), 32.74 (d, J=70.1Hz)31P NMR(162MHz,DMSO-d6)δ27.89.HRMS(ESI-):
calculated m/z[M-H]-for[C21H18O3P]-:349.0999,found:349.0999.
Embodiment 4
A kind of compound containing phosphine carboxylic acid, chemical structural formula are as follows:
Its reaction equation are as follows:
The compound the preparation method comprises the following steps:
(1) 2mg, 2mol%4CzIPN is added in 10mL dry Shrek pipe, reaction tube is then transferred to glove box
Middle addition 49mg, 0.24mmol diphenyl phosphine oxide (2a) and 98mg, 0.3mmol cesium carbonate；
(2) reaction tube is taken out and is connected afterwards with the biexhaust pipe for being connected with carbon dioxide steel cylinder, taken out on biexhaust pipe and fill titanium dioxide
Carbon 3 times, the nitrogen in drain makes that 2mL DMF is then added under carbon dioxide atmosphere full of carbon dioxide gas in its pipe
With 21 μ L, 0.2mmol methyl methacrylates (10a)；
(3) finally, placing reaction liquid into away from 30W blue LED lamp 2-3cm, stirring 12 hours under room temperature (25 DEG C), so
4.5mL water and 0.5mL 2N hydrochloric acid mixture are used afterwards, then is extracted with ethyl acetate reaction mixture at least 3 times, are extracted
To organic phase merge after directly concentration be spin-dried for.Residue (eluant, eluent PE/EA 2/1~1/1: is contained by flash column chromatography
0.2-0.6%AcOH) obtain pure required product, yield 85%.
The compound is white solid, nuclear magnetic data are as follows:1H NMR(400MHz,DMSO-d6)δ13.15(s,1H),
7.89–7.77(m,4H),7.60–7.45(m,6H),3.44(s,3H),3.16–2.93(m,2H),1.35(s,3H).13C NMR
(101MHz,DMSO-d6) δ 172.79 (d, J=12.6Hz), 171.34 (d, J=6.3Hz), 135.32 (d, J=98.0Hz),
134.91 (d, J=98.1Hz), 132.02 (d, J=2.6Hz), 131.97 (d, J=2.6Hz), 130.71 (d, J=9.4Hz),
130.65 (d, J=9.3Hz), 52.61,51.29 (d, J=2.5Hz), 34.95 (d, J=71.1Hz), 21.09 (d, J=
2.7Hz).31P NMR(162MHz,DMSO-d6)δ25.18.HRMS(ESI+):calculated m/z[M+H]+for
[C18H19O5PH]+:347.1043,found:347.1042.
Comparative example 1
Compared with Example 1, lack potassium carbonate in step (1), remaining process is same as Example 1；Then detection system
The yield of standby obtained compound is 21%.
Comparative example 2
Compared with Example 1, lack photochemical catalyst in reaction process, remaining process is same as Example 1；Then it detects
The yield for the compound being prepared is 0%.
Comparative example 3
Compared with Example 1, lack illumination in reaction process, remaining process is same as Example 1；Most then detection is made
The yield of standby obtained compound is 0%.
Comparative example 4
Compared with Example 1, lack carbon dioxide in reaction process, remaining process is same as Example 1；Then it detects
The yield for the compound being prepared is less than 5%.
Thus illustrate, only under the cooperation of reaction condition of the present invention, could efficiently synthesize the carboxylic acid compound containing phosphine.
Claims (10)
1. a kind of compound containing phosphine carboxylic acid, general formula of the chemical structure are as follows:
Wherein, X is aromatic radical, with any one of aromatic radical, alkyl or alkoxy replaced；A is hydrogen, alkyl, amido, band
The amino of protection, aryl, heteroaryl, with the aromatic radical replaced or with any one of substituted heteroaryl, ester group or hydroxyl；B
For hydrogen, alkyl, amido, with protection amino, aryl, heteroaryl, band substitution aromatic radical or with substituted heteroaryl, ester group or
Any one of hydroxyl；C is hydrogen or alkyl.
2. compound containing phosphine carboxylic acid according to claim 1, which is characterized in that its chemical structural formula is
Wherein, X is aromatic radical, with aromatic radical, alkyl or the alkoxy replaced；
R1For aromatic radical, with the aromatic radical replaced or with substituted heteroaryl；R2Replace for aromatic radical, with aromatic radical, the band replaced
Heteroaryl, any one in alkyl；R3For any one in hydrogen, alkyl or branched alkyl；
R4For aromatic radical, with the aromatic radical replaced or with any one in substituted heteroaryl；R5For hydrogen, alkyl or replace alkane
Any one in base；R6For any one in hydrogen, alkyl or branched alkyl；
R7For aromatic radical, with the aromatic radical replaced or with any one in substituted heteroaryl；R8For hydrogen, alkyl or replace alkane
Any one in base；
R9For any one in the alkyl of hydrogen, alkyl, branched alkyl or hetero atom substitution；R10For aryl, heteroaryl or substitution
Aryl, any one in heteroaryl or alkyl.
3. compound containing phosphine carboxylic acid according to claim 1 or 2, which is characterized in that its chemical structural formula are as follows:
4. a kind of method for preparing the compound as claimed in claim 1 or 2 containing phosphine carboxylic acid, which comprises the following steps:
By reaction substrate and phosphine oxide compound and alkali mixed dissolution, photochemical catalyst is then added in carbon dioxide atmosphere, then
In 10~60 DEG C, 1~100W illumination reaction 2~for 24 hours；
Wherein, the additive amount of the phosphine oxide compound is 1~3 times of the amount of reaction substrate substance；The additive amount of alkali is reaction bottom
1~20 times of the amount of object substance；The additive amount of photochemical catalyst is the 0.1~5% of the amount of reaction substrate substance；
The reaction substrate is enamides, olefin(e) compound, enol silyl ether compound or acrylic ester compound.
5. according to the method described in claim 4, it is characterized in that, the phosphine oxide compound is aryl phosphine oxide compound, phosphonic acids
Ester type compound or alkyl phosphine oxide compound；The alkali is potassium carbonate, sodium carbonate or cesium carbonate.
6. according to the method described in claim 4, it is characterized in that, the photochemical catalyst is 4CzIPN, Ir [(ppy)2
(dtbppy)]PF6、Ir[(ppy)2(dtbppy)]PF6 Ir[dF(CF3)ppy]2(dtbbpy)PF6Or Ir [dF (Me) ppy]2
(dtbbpy)PF6。
7. according to the method described in claim 4, it is characterized in that, the reaction condition are as follows: in carbon dioxide atmosphere, in 20
~25 DEG C, 30~35W illumination reaction, 10~12h.
8. according to the method described in claim 4, it is characterized in that, the light source that uses of when illumination reaction is blue light.
9. according to the method described in claim 4, it is characterized by further comprising: after reaction, with sour quenching reaction product,
It is extracted with ethyl acetate again at least 5 times, and the organic phase extracted every time is merged and is concentrated, then is pure to enriched product progress column chromatography
Change.
10. according to the method described in claim 9, it is characterized in that, the eluant, eluent that the column uses when chromatographing is that volume ratio is
The methylene chloride-methanol mixed liquor or volume ratio of 100:1~20:1 is the petroleum ether-ethyl acetate mixed liquor of 2:1~1:1, and
Be added in the methylene chloride-methanol mixed liquor and petroleum ether-ethyl acetate mixed liquor it is promising account for its total volume 0.1~
0.6% glacial acetic acid.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910599890.5A CN110256492B (en) | 2019-07-04 | 2019-07-04 | Phosphonic-containing carboxylic acid compound and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910599890.5A CN110256492B (en) | 2019-07-04 | 2019-07-04 | Phosphonic-containing carboxylic acid compound and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110256492A true CN110256492A (en) | 2019-09-20 |
| CN110256492B CN110256492B (en) | 2020-12-01 |
Family
ID=67924366
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910599890.5A Active CN110256492B (en) | 2019-07-04 | 2019-07-04 | Phosphonic-containing carboxylic acid compound and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110256492B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111995641A (en) * | 2020-08-28 | 2020-11-27 | 山东卓俊实业有限公司 | Production method of alkyl phosphine |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001253891A (en) * | 2000-03-13 | 2001-09-18 | Natl Inst Of Advanced Industrial Science & Technology Meti | Phosphinyl group-containing n-substituted amino acid derivative and method for producing the same |
| CN108752232A (en) * | 2018-05-14 | 2018-11-06 | 四川大学 | A kind of synthetic method of α-quaternary carbon amino acid |
-
2019
- 2019-07-04 CN CN201910599890.5A patent/CN110256492B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001253891A (en) * | 2000-03-13 | 2001-09-18 | Natl Inst Of Advanced Industrial Science & Technology Meti | Phosphinyl group-containing n-substituted amino acid derivative and method for producing the same |
| CN108752232A (en) * | 2018-05-14 | 2018-11-06 | 四川大学 | A kind of synthetic method of α-quaternary carbon amino acid |
Non-Patent Citations (3)
| Title |
|---|
| EDWARD E. SCHWEIZER ET AL.,: ""Reactions of phosphorus compounds. XXVI. Preparation and reactions of 3- and 4-substituted 5-benzoyl-2,2,2,5-tetraphenyl-2-oxaphospholanes"", 《JOURNAL OF ORGANIC CHEMISTRY》 * |
| REHAN AHMED ET AL.,: ""Phosphorus-Based Functional Groups as Hydrogen Bonding Templates for Rotaxane Formation"", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| TAISUKE ITAYA ET AL.,: ""Synthesis and absolute configuration of wybutine, the fluorescent minor base from phenylalanine transfer ribonucleic acids"", 《CHEMICAL & PHARMACEUTICAL BULLETIN》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111995641A (en) * | 2020-08-28 | 2020-11-27 | 山东卓俊实业有限公司 | Production method of alkyl phosphine |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110256492B (en) | 2020-12-01 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Wang et al. | Synthesis of a new type of chiral amino phosphine ligands for asymmetric catalysis | |
| CN109704926B (en) | Anticancer active molecular skeleton 1, 4-eneyne compound and preparation method and application thereof | |
| CN112358427B (en) | Synthetic method of trifluoro-methyl-thionate compound | |
| CN110041362B (en) | Method for photocatalytic synthesis of 1-alkyl-1-phosphonocyclopropane | |
| CN107082789A (en) | A kind of method to prepare organophosphorus ester compound containing P (O) OH classes compound and the efficient esterification of phenol | |
| CN108912042A (en) | A method of aromatic ketone is directly prepared from aromatic acid | |
| CN107573360A (en) | A kind of Mutiple Targets micromolecular compound S63845 preparation method | |
| CN107540574A (en) | The preparation method of R biphenyl Propanolamines | |
| CN110256492A (en) | One kind compound containing phosphine carboxylic acid and preparation method thereof | |
| CN109265475A (en) | A kind of preparation method of polysubstituted aryl ethylene pinacol borate derivative | |
| CN110172028A (en) | A kind of method of industrialized production tulobuterol | |
| CN109867695B (en) | Novel preparation method of pitavastatin calcium intermediate | |
| CN106866480B (en) | Polycyclic virtue selenide analog derivative and preparation method thereof | |
| CN102212075A (en) | Preparation method for cefbuperazone | |
| CN113548965B (en) | Preparation method of 1,4 eneyne compound | |
| CN108484451A (en) | A kind of method that one kettle way prepares 1,2- alkamine compounds | |
| CN102199154B (en) | Novel synthesis method for pyrrole derivatives | |
| CN104945231B (en) | Method for synthesizing 1,4-diketone compound by using 2-halogenated cyclopentanone as raw material | |
| CN103665038B (en) | A kind of carbon phosphorus chirality dialkyl phosphine oxide and synthetic method thereof | |
| CN111320664B (en) | Preparation method of 24-cholenenoic acid ethyl ester | |
| CN113444040A (en) | Method for synthesizing chiral alpha-unnatural amino acid derivative under drive of visible light | |
| CN101440076A (en) | Process for synthesizing optical activity 2-(1'(Z) alkenyl iodo-alkyl) tetrahydrofuran | |
| CN107629039B (en) | The preparation method and intermediate of deuterated acrylamide | |
| CN105669517B (en) | A kind of process for catalytic synthesis of Benzazole compounds | |
| CN106966937A (en) | Diaryl selenide analog derivative and preparation method thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |