JPS6087293A - ホスフィン酸中間体の製造法 - Google Patents
ホスフィン酸中間体の製造法Info
- Publication number
- JPS6087293A JPS6087293A JP59195642A JP19564284A JPS6087293A JP S6087293 A JPS6087293 A JP S6087293A JP 59195642 A JP59195642 A JP 59195642A JP 19564284 A JP19564284 A JP 19564284A JP S6087293 A JPS6087293 A JP S6087293A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- lower alkyl
- ester
- item
- molar ratio
- 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
- 238000004519 manufacturing process Methods 0.000 title claims description 9
- ACVYVLVWPXVTIT-UHFFFAOYSA-N phosphinic acid Chemical compound O[PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-N 0.000 title claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 39
- 125000000217 alkyl group Chemical group 0.000 claims description 33
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical group CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 22
- 150000002148 esters Chemical class 0.000 claims description 20
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- -1 phosphonous acid ester Chemical class 0.000 claims description 13
- XRBCRPZXSCBRTK-UHFFFAOYSA-N phosphonous acid Chemical compound OPO XRBCRPZXSCBRTK-UHFFFAOYSA-N 0.000 claims description 12
- 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 claims description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 7
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 3
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical group C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- YFMLAZBUXVEFHJ-UHFFFAOYSA-N 2,2,2-trifluoro-N-silylacetamide Chemical compound FC(F)(F)C(=O)N[SiH3] YFMLAZBUXVEFHJ-UHFFFAOYSA-N 0.000 claims description 2
- NCLIGEZQAPUUQU-UHFFFAOYSA-N 2-silylacetamide Chemical compound NC(=O)C[SiH3] NCLIGEZQAPUUQU-UHFFFAOYSA-N 0.000 claims description 2
- LPHRTQQOKYRTQS-UHFFFAOYSA-N NC(=O)C([SiH3])[SiH3] Chemical compound NC(=O)C([SiH3])[SiH3] LPHRTQQOKYRTQS-UHFFFAOYSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- NRKYWOKHZRQRJR-UHFFFAOYSA-N 2,2,2-trifluoroacetamide Chemical compound NC(=O)C(F)(F)F NRKYWOKHZRQRJR-UHFFFAOYSA-N 0.000 claims 1
- 239000012528 membrane Substances 0.000 claims 1
- 238000006884 silylation reaction Methods 0.000 claims 1
- 239000002966 varnish Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 9
- 239000000543 intermediate Substances 0.000 description 7
- PJOFGDOSMWTOOQ-UHFFFAOYSA-N 4-phenylbutylphosphonic acid Chemical compound OP(O)(=O)CCCCC1=CC=CC=C1 PJOFGDOSMWTOOQ-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000004414 alkyl thio group Chemical group 0.000 description 3
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- ZJLCWRUFLIMZFW-UHFFFAOYSA-N 4-phenylbutylphosphonous acid Chemical compound OP(O)CCCCC1=CC=CC=C1 ZJLCWRUFLIMZFW-UHFFFAOYSA-N 0.000 description 2
- 239000005541 ACE inhibitor Substances 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 2
- 229940044094 angiotensin-converting-enzyme inhibitor Drugs 0.000 description 2
- 125000001589 carboacyl group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000004435 hydrogen atom Chemical class [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
- 239000011541 reaction mixture Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- MBODXUXQQPORNR-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)prop-2-en-1-one Chemical compound C1=CC=C2N(C(=O)C=C)CCC2=C1 MBODXUXQQPORNR-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WLXLAXUWFYEPED-UHFFFAOYSA-N 2-cyanoethyl(4-phenylbutyl)phosphinic acid Chemical compound N#CCCP(=O)(O)CCCCC1=CC=CC=C1 WLXLAXUWFYEPED-UHFFFAOYSA-N 0.000 description 1
- NPRGTRPCLILHAO-UHFFFAOYSA-N 3-[hydroxy(4-phenylbutyl)phosphoryl]propanoic acid Chemical compound OC(=O)CCP(O)(=O)CCCCC1=CC=CC=C1 NPRGTRPCLILHAO-UHFFFAOYSA-N 0.000 description 1
- AUGKLUNRHYPDAM-UHFFFAOYSA-N 3-methylbut-2-enenitrile Chemical compound CC(C)=CC#N AUGKLUNRHYPDAM-UHFFFAOYSA-N 0.000 description 1
- 101710129690 Angiotensin-converting enzyme inhibitor Proteins 0.000 description 1
- OGBVRMYSNSKIEF-UHFFFAOYSA-N Benzylphosphonic acid Chemical group OP(O)(=O)CC1=CC=CC=C1 OGBVRMYSNSKIEF-UHFFFAOYSA-N 0.000 description 1
- 101710086378 Bradykinin-potentiating and C-type natriuretic peptides Proteins 0.000 description 1
- MFBJPFUECRZDQP-UHFFFAOYSA-N CCOP(=O)CCCC(C(C)C(O)=O)C1=CC=CC=C1 Chemical compound CCOP(=O)CCCC(C(C)C(O)=O)C1=CC=CC=C1 MFBJPFUECRZDQP-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- URSMVHPQVALPBQ-UHFFFAOYSA-N butyl(methoxy)phosphinous acid Chemical compound CCCCP(O)OC URSMVHPQVALPBQ-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 1
- FBSFTJQYCLLGKH-UHFFFAOYSA-N cyclohexylphosphonic acid Chemical compound OP(O)(=O)C1CCCCC1 FBSFTJQYCLLGKH-UHFFFAOYSA-N 0.000 description 1
- HBYXSLLRTLMMNK-UHFFFAOYSA-N cyclopentylphosphonic acid Chemical compound OP(O)(=O)C1CCCC1 HBYXSLLRTLMMNK-UHFFFAOYSA-N 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- IRHNDRJMWREYTP-UHFFFAOYSA-N ethoxy(propyl)phosphinous acid Chemical compound CCCP(O)OCC IRHNDRJMWREYTP-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- YIGLRRLMAMUSIO-ZETCQYMHSA-N methyl (2s)-1-prop-2-enoylpyrrolidine-2-carboxylate Chemical compound COC(=O)[C@@H]1CCCN1C(=O)C=C YIGLRRLMAMUSIO-ZETCQYMHSA-N 0.000 description 1
- WITYUUTUSPKOAB-UHFFFAOYSA-N methyl 2-methyl-2-phenylpropanoate Chemical compound COC(=O)C(C)(C)C1=CC=CC=C1 WITYUUTUSPKOAB-UHFFFAOYSA-N 0.000 description 1
- CQTRCIZQRVOJME-UHFFFAOYSA-N methyl 2-phenylbut-2-enoate Chemical compound COC(=O)C(=CC)C1=CC=CC=C1 CQTRCIZQRVOJME-UHFFFAOYSA-N 0.000 description 1
- KHCHUBDYIXGFBM-UHFFFAOYSA-N methyl 3-ethylpent-2-enoate Chemical compound CCC(CC)=CC(=O)OC KHCHUBDYIXGFBM-UHFFFAOYSA-N 0.000 description 1
- BDPBIUDBBLLCPA-UHFFFAOYSA-N methyl 3-ethylpentanoate Chemical compound CCC(CC)CC(=O)OC BDPBIUDBBLLCPA-UHFFFAOYSA-N 0.000 description 1
- MCVVUJPXSBQTRZ-UHFFFAOYSA-N methyl but-2-enoate Chemical compound COC(=O)C=CC MCVVUJPXSBQTRZ-UHFFFAOYSA-N 0.000 description 1
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 1
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229940088644 n,n-dimethylacrylamide Drugs 0.000 description 1
- YLGYACDQVQQZSW-UHFFFAOYSA-N n,n-dimethylprop-2-enamide Chemical compound CN(C)C(=O)C=C YLGYACDQVQQZSW-UHFFFAOYSA-N 0.000 description 1
- SFDJOSRHYKHMOK-UHFFFAOYSA-N nitramide Chemical compound N[N+]([O-])=O SFDJOSRHYKHMOK-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- NSETWVJZUWGCKE-UHFFFAOYSA-N propylphosphonic acid Chemical compound CCCP(O)(O)=O NSETWVJZUWGCKE-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood 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
- C07F9/547—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
- C07F9/62—Isoquinoline or hydrogenated isoquinoline 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
- C07F9/28—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)]
- C07F9/301—Acyclic saturated acids which can have further substituents on alkyl
-
- 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)]
- C07F9/303—Cycloaliphatic 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/304—Aromatic acids (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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/306—Arylalkanephosphinic acids, e.g. Ar-(CH2)n-P(=X)(R)(XH), (X = O,S, Se; n>=1)
-
- 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)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3211—Esters of acyclic saturated acids which can have further substituents on alkyl
-
- 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)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3223—Esters of cycloaliphatic 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
- C07F9/30—Phosphinic acids [R2P(=O)(OH)]; Thiophosphinic acids ; [R2P(=X1)(X2H) (X1, X2 are each independently O, S or Se)]
- C07F9/32—Esters thereof
- C07F9/3205—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/3241—Esters of arylalkanephosphinic 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
- C07F9/547—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
-
- 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
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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53348683A | 1983-09-19 | 1983-09-19 | |
| US533486 | 2000-03-23 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6087293A true JPS6087293A (ja) | 1985-05-16 |
| JPH0473437B2 JPH0473437B2 (enrdf_load_stackoverflow) | 1992-11-20 |
Family
ID=24126167
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59195642A Granted JPS6087293A (ja) | 1983-09-19 | 1984-09-17 | ホスフィン酸中間体の製造法 |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPS6087293A (enrdf_load_stackoverflow) |
| CA (1) | CA1258458A (enrdf_load_stackoverflow) |
| DE (1) | DE3434124A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2552090B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2146644B (enrdf_load_stackoverflow) |
| IT (1) | IT1176710B (enrdf_load_stackoverflow) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007238617A (ja) * | 2006-03-07 | 2007-09-20 | Clariant Internatl Ltd | モノカルボキシ官能化ジアルキルホスフィン酸塩から組成される混合物、それの使用及び製造方法 |
| JP2012507474A (ja) * | 2008-11-05 | 2012-03-29 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | アルキルアルコール／アクロレインを使用したジアルキルホスフィン酸、−エステル及び−塩の製造方法及びそれらの使用 |
| JP2012507476A (ja) * | 2008-11-05 | 2012-03-29 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | アクロレイン類によるモノヒドロキシ官能化ジアルキルホスフィン酸、そのエステルおよび塩の製造方法ならびにその使用 |
| JP2012508197A (ja) * | 2008-11-07 | 2012-04-05 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | アクリロニトリルによるモノアミノ官能化ジアルキルホスフィン酸類、そのエステル類および塩類の製造方法、ならびにこれらの使用。 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168267A (en) * | 1978-10-23 | 1979-09-18 | E. R. Squibb & Sons, Inc. | Phosphinylalkanoyl prolines |
-
1984
- 1984-09-17 DE DE19843434124 patent/DE3434124A1/de active Granted
- 1984-09-17 JP JP59195642A patent/JPS6087293A/ja active Granted
- 1984-09-17 GB GB08423458A patent/GB2146644B/en not_active Expired
- 1984-09-18 IT IT22707/84A patent/IT1176710B/it active
- 1984-09-18 CA CA000463513A patent/CA1258458A/en not_active Expired
- 1984-09-19 FR FR8414378A patent/FR2552090B1/fr not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007238617A (ja) * | 2006-03-07 | 2007-09-20 | Clariant Internatl Ltd | モノカルボキシ官能化ジアルキルホスフィン酸塩から組成される混合物、それの使用及び製造方法 |
| JP2012507474A (ja) * | 2008-11-05 | 2012-03-29 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | アルキルアルコール／アクロレインを使用したジアルキルホスフィン酸、−エステル及び−塩の製造方法及びそれらの使用 |
| JP2012507476A (ja) * | 2008-11-05 | 2012-03-29 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | アクロレイン類によるモノヒドロキシ官能化ジアルキルホスフィン酸、そのエステルおよび塩の製造方法ならびにその使用 |
| JP2012508197A (ja) * | 2008-11-07 | 2012-04-05 | クラリアント・ファイナンス・（ビーブイアイ）・リミテッド | アクリロニトリルによるモノアミノ官能化ジアルキルホスフィン酸類、そのエステル類および塩類の製造方法、ならびにこれらの使用。 |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2146644B (en) | 1987-05-13 |
| IT1176710B (it) | 1987-08-18 |
| DE3434124C2 (enrdf_load_stackoverflow) | 1993-07-01 |
| CA1258458A (en) | 1989-08-15 |
| IT8422707A0 (it) | 1984-09-18 |
| FR2552090B1 (fr) | 1987-01-09 |
| JPH0473437B2 (enrdf_load_stackoverflow) | 1992-11-20 |
| GB2146644A (en) | 1985-04-24 |
| GB8423458D0 (en) | 1984-10-24 |
| DE3434124A1 (de) | 1985-04-04 |
| FR2552090A1 (fr) | 1985-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4602092A (en) | Method for making phosphinic acid intermediates | |
| US4594199A (en) | Method for making phosphinic acid intermediates | |
| JP4332902B2 (ja) | 新規ジヒドロピリジン誘導体 | |
| JPS6087293A (ja) | ホスフィン酸中間体の製造法 | |
| Arrieta et al. | Syntheses of β-lactams from acetic acids and imines induced by phenyl dichlorophosphate reagent | |
| US5008399A (en) | Diastereoselective preparation of phosphinate esters | |
| CA1258457A (en) | Process for preparing phosphinic acid intermediates | |
| Green et al. | The preparation and characterization of some fluorinated α-aminoarylmethanephosphonic acids | |
| JP3100444B2 (ja) | １，４−ジヒドロピリジン誘導体及びその製造方法 | |
| JPH0141639B2 (enrdf_load_stackoverflow) | ||
| US4140691A (en) | Process for preparing 3-[2-(4-benzamidopiperid-1-yl)ethyl]indole | |
| US5608098A (en) | Bis(aminomethyl)phosphinic acid derivatives and process for the preparation of bis(aminomethyl)phosphinic acid derivatives | |
| JP3763001B2 (ja) | 非対称セレノホスフィン酸塩化物及びその製造方法 | |
| Fabbri et al. | Binaphthyl-Substituted Chiral Phosphines and Oxides from Binaphthophooles and Nucleophiles | |
| US5633385A (en) | Optically active ω-halo-2-amino-alkanecarboxylic acid derivatives, process for the preparation thereof and their use for the preparation of optically active phosphorus-containing α-amino acids | |
| JP3168563B2 (ja) | ホスネートｎｍｄａ拮抗剤の調製用ｎ−トリチルアスパラギン酸誘導体類 | |
| Chaikovskaya et al. | Synthesis of 3‐aryl (hetaryl)‐1, 2, 3‐diazaphospholines | |
| JPS604830B2 (ja) | フエニル酢酸誘導体 | |
| US5554773A (en) | N-trityl protected aspartic acid derivatives for the preparation of phosphonate NMDA antagonists | |
| JP3006904B2 (ja) | １，４−ジヒドロピリジン誘導体の製造法及びその中間体 | |
| KR100667673B1 (ko) | Ｄ（―）페닐알라닌 유도체의 제조방법 | |
| JP4081588B2 (ja) | Ｎ−トリアルキルメチルカルボニル−２−アルキル−３，４−ジフルオロアニリンの製造方法 | |
| CN1086218A (zh) | 抗炎剂膦酰基乙酸酯和酸 | |
| JPH02273688A (ja) | 環状亜リン酸エステル誘導体 | |
| JPH09502193A (ja) | 抗高血糖症および／または抗肥満症活性を有するホスフィン酸誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EXPY | Cancellation because of completion of term |