IE32525B1 - Cis-propenyl phosphonic acid and derivatives thereof - Google Patents
Cis-propenyl phosphonic acid and derivatives thereofInfo
- Publication number
- IE32525B1 IE32525B1 IE1257/68A IE125768A IE32525B1 IE 32525 B1 IE32525 B1 IE 32525B1 IE 1257/68 A IE1257/68 A IE 1257/68A IE 125768 A IE125768 A IE 125768A IE 32525 B1 IE32525 B1 IE 32525B1
- Authority
- IE
- Ireland
- Prior art keywords
- cis
- propenyl
- acid
- compounds
- phosphonic acid
- Prior art date
Links
- XWCIXXXLOAAWPU-IHWYPQMZSA-N [(z)-prop-1-enyl]phosphonic acid Chemical compound C\C=C/P(O)(O)=O XWCIXXXLOAAWPU-IHWYPQMZSA-N 0.000 title abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 7
- -1 propynyl compound Chemical class 0.000 abstract 7
- 150000003839 salts Chemical class 0.000 abstract 6
- 150000004820 halides Chemical class 0.000 abstract 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001408 amides Chemical class 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 125000005843 halogen group Chemical group 0.000 abstract 3
- 238000005984 hydrogenation reaction Methods 0.000 abstract 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 abstract 2
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Substances 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 238000010438 heat treatment Methods 0.000 abstract 2
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 150000003009 phosphonic acids Chemical class 0.000 abstract 2
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 abstract 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- XYPISWUKQGWYGX-UHFFFAOYSA-N 2,2,2-trifluoroethaneperoxoic acid Chemical compound OOC(=O)C(F)(F)F XYPISWUKQGWYGX-UHFFFAOYSA-N 0.000 abstract 1
- WUEAMTVQNGYLRI-UHFFFAOYSA-N 2-dichlorophosphoryl-1,3,5-tri(propan-2-yl)benzene Chemical compound CC(C)C1=CC(C(C)C)=C(P(Cl)(Cl)=O)C(C(C)C)=C1 WUEAMTVQNGYLRI-UHFFFAOYSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007818 Grignard reagent Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 abstract 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 abstract 1
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910021529 ammonia Inorganic materials 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- MCKANBCWFDYIJO-UHFFFAOYSA-N chloro-dihydroxy-imino-$l^{5}-phosphane Chemical compound NP(O)(Cl)=O MCKANBCWFDYIJO-UHFFFAOYSA-N 0.000 abstract 1
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical compound OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 150000001470 diamides Chemical class 0.000 abstract 1
- 150000005690 diesters Chemical class 0.000 abstract 1
- LGTLXDJOAJDFLR-UHFFFAOYSA-N diethyl chlorophosphate Chemical compound CCOP(Cl)(=O)OCC LGTLXDJOAJDFLR-UHFFFAOYSA-N 0.000 abstract 1
- XQRLCLUYWUNEEH-UHFFFAOYSA-N diphosphonic acid Chemical compound OP(=O)OP(O)=O XQRLCLUYWUNEEH-UHFFFAOYSA-N 0.000 abstract 1
- 238000006735 epoxidation reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- JGJLWPGRMCADHB-UHFFFAOYSA-N hypobromite Inorganic materials Br[O-] JGJLWPGRMCADHB-UHFFFAOYSA-N 0.000 abstract 1
- 229940046892 lead acetate Drugs 0.000 abstract 1
- OYICOGPBEIHJEO-UHFFFAOYSA-L magnesium;acetylene;dibromide Chemical compound [Mg+2].[Br-].[Br-].C#C OYICOGPBEIHJEO-UHFFFAOYSA-L 0.000 abstract 1
- 125000002757 morpholinyl group Chemical group 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 230000003287 optical effect Effects 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 125000004430 oxygen atom Chemical group O* 0.000 abstract 1
- 125000005541 phosphonamide group Chemical group 0.000 abstract 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 abstract 1
- FUWGSUOSJRCEIV-UHFFFAOYSA-N phosphonothioic O,O-acid Chemical compound OP(O)=S FUWGSUOSJRCEIV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 231100000572 poisoning Toxicity 0.000 abstract 1
- 230000000607 poisoning effect Effects 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000008929 regeneration Effects 0.000 abstract 1
- 238000011069 regeneration method Methods 0.000 abstract 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 1
- 229910001961 silver nitrate Inorganic materials 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003573 thiols Chemical class 0.000 abstract 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000004246 zinc acetate Substances 0.000 abstract 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
- C07F9/655—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
- C07F9/65502—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 three-membered ring
- C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
-
- 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
- C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
-
- 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)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US67920367A | 1967-10-30 | 1967-10-30 | |
| US72942068A | 1968-05-15 | 1968-05-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE32525L IE32525L (en) | 1969-04-30 |
| IE32525B1 true IE32525B1 (en) | 1973-09-05 |
Family
ID=27102173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE1257/68A IE32525B1 (en) | 1967-10-30 | 1968-10-21 | Cis-propenyl phosphonic acid and derivatives thereof |
Country Status (15)
| Country | Link |
|---|---|
| AT (1) | AT292731B (enExample) |
| BE (1) | BE723071A (enExample) |
| CH (1) | CH531012A (enExample) |
| DK (1) | DK132585C (enExample) |
| ES (1) | ES359538A1 (enExample) |
| FI (1) | FI51357C (enExample) |
| FR (1) | FR1592151A (enExample) |
| GB (1) | GB1239988A (enExample) |
| IE (1) | IE32525B1 (enExample) |
| IL (1) | IL30902A0 (enExample) |
| LU (1) | LU57182A1 (enExample) |
| MT (1) | MTP579B (enExample) |
| NL (1) | NL6814978A (enExample) |
| NO (1) | NO133200C (enExample) |
| SE (1) | SE369910B (enExample) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA774977B (en) * | 1976-09-06 | 1978-06-28 | Sab Soc Etudes Applic Biolog | Process for the preparation of 1,2-expoxypropyl-phosphonic acid derivatives |
| EP2270021A1 (en) | 2009-06-18 | 2011-01-05 | Centre National de la Recherche Scientifique | Phosphonates synthons for the synthesis of phosphonates derivatives showing better bioavailability |
| CN120865288B (zh) * | 2025-09-28 | 2025-11-28 | 苏州开元民生科技股份有限公司 | 一种磷霉素中间体左磷右胺盐的合成方法 |
-
1968
- 1968-10-18 NL NL6814978A patent/NL6814978A/xx unknown
- 1968-10-20 IL IL30902A patent/IL30902A0/xx unknown
- 1968-10-21 CH CH1569868A patent/CH531012A/de not_active IP Right Cessation
- 1968-10-21 IE IE1257/68A patent/IE32525B1/xx unknown
- 1968-10-24 GB GB50636/68A patent/GB1239988A/en not_active Expired
- 1968-10-25 ES ES359538A patent/ES359538A1/es not_active Expired
- 1968-10-29 DK DK521968A patent/DK132585C/da active
- 1968-10-29 LU LU57182D patent/LU57182A1/xx unknown
- 1968-10-29 BE BE723071D patent/BE723071A/xx unknown
- 1968-10-29 FI FI683065A patent/FI51357C/fi active
- 1968-10-29 NO NO4276/68A patent/NO133200C/no unknown
- 1968-10-29 SE SE14617/68A patent/SE369910B/xx unknown
- 1968-10-30 MT MT579A patent/MTP579B/xx unknown
- 1968-10-30 FR FR1592151D patent/FR1592151A/fr not_active Expired
- 1968-10-30 AT AT1055368A patent/AT292731B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| NL6814978A (enExample) | 1969-05-02 |
| AT292731B (de) | 1971-09-10 |
| LU57182A1 (enExample) | 1969-05-16 |
| MTP579B (en) | 1969-10-13 |
| DK132585C (da) | 1976-05-31 |
| NO133200B (enExample) | 1975-12-15 |
| DE1805677A1 (de) | 1969-12-11 |
| IE32525L (en) | 1969-04-30 |
| BE723071A (enExample) | 1969-04-29 |
| DK132585B (da) | 1976-01-05 |
| SE369910B (enExample) | 1974-09-23 |
| ES359538A1 (es) | 1970-08-16 |
| GB1239988A (en) | 1971-07-21 |
| NO133200C (enExample) | 1976-03-24 |
| CH531012A (de) | 1972-11-30 |
| FI51357B (enExample) | 1976-08-31 |
| IL30902A0 (en) | 1969-02-27 |
| FI51357C (fi) | 1976-12-10 |
| FR1592151A (enExample) | 1970-05-11 |
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