CA1249995A - Composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinylique - Google Patents
Composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinyliqueInfo
- Publication number
- CA1249995A CA1249995A CA000306092A CA306092A CA1249995A CA 1249995 A CA1249995 A CA 1249995A CA 000306092 A CA000306092 A CA 000306092A CA 306092 A CA306092 A CA 306092A CA 1249995 A CA1249995 A CA 1249995A
- Authority
- CA
- Canada
- Prior art keywords
- cis
- dimethyl
- acid
- cyclopropane
- compound
- 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.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 42
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 title description 12
- 150000001942 cyclopropanes Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims abstract description 19
- 239000000460 chlorine Substances 0.000 claims abstract description 17
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 230000008569 process Effects 0.000 claims abstract description 11
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000011737 fluorine Substances 0.000 claims abstract description 5
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 67
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 28
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 27
- 150000002596 lactones Chemical class 0.000 claims description 26
- 239000000203 mixture Substances 0.000 claims description 24
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 17
- -1 acids 2,2-dimethyl-cyclopropane-1-carboxylic compounds Chemical class 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 10
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 claims description 9
- SXJFAUMLDVVAOH-UHFFFAOYSA-N 2,2-dimethyl-3-(2,2,2-tribromo-1-hydroxyethyl)cyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(O)C(Br)(Br)Br)C1C(O)=O SXJFAUMLDVVAOH-UHFFFAOYSA-N 0.000 claims description 8
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 6
- 230000009471 action Effects 0.000 claims description 5
- 239000003153 chemical reaction reagent Substances 0.000 claims description 5
- 239000003638 chemical reducing agent Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- FLVIBMHIOTVKSY-UHFFFAOYSA-N 2,2-dimethyl-3-(2,2,2-trichloro-1-hydroxyethyl)cyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(O)C(Cl)(Cl)Cl)C1C(O)=O FLVIBMHIOTVKSY-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 claims description 4
- 239000012024 dehydrating agents Substances 0.000 claims description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 3
- 239000011701 zinc Substances 0.000 claims description 3
- 229910052725 zinc Inorganic materials 0.000 claims description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 238000006482 condensation reaction Methods 0.000 claims description 2
- 230000008030 elimination Effects 0.000 claims description 2
- 238000003379 elimination reaction Methods 0.000 claims description 2
- 150000002170 ethers Chemical class 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- ASKVAQUVJBPTBK-UHFFFAOYSA-N 6,6-dimethyl-4-(tribromomethyl)-3-oxabicyclo[3.1.0]hexan-2-one Chemical compound O=C1OC(C(Br)(Br)Br)C2C1C2(C)C ASKVAQUVJBPTBK-UHFFFAOYSA-N 0.000 claims 2
- FEYOSLIYFUIJFC-UHFFFAOYSA-N 6,6-dimethyl-4-(trichloromethyl)-3-oxabicyclo[3.1.0]hexan-2-one Chemical compound O=C1OC(C(Cl)(Cl)Cl)C2C1C2(C)C FEYOSLIYFUIJFC-UHFFFAOYSA-N 0.000 claims 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims 2
- 150000001768 cations Chemical class 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- APUDZIAZJZNIKT-UHFFFAOYSA-N 3-(2,2-dichloro-2-fluoro-1-hydroxyethyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C(O)C(F)(Cl)Cl)C1C(O)=O APUDZIAZJZNIKT-UHFFFAOYSA-N 0.000 claims 1
- 239000001294 propane Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000243 solution Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 14
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000007864 aqueous solution Substances 0.000 description 11
- 229950011148 cyclopropane Drugs 0.000 description 11
- 150000007513 acids Chemical class 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 7
- 230000009102 absorption Effects 0.000 description 7
- 238000010521 absorption reaction Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 5
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- BFAKENXZKHGIGE-UHFFFAOYSA-N bis(2,3,5,6-tetrafluoro-4-iodophenyl)diazene Chemical compound FC1=C(C(=C(C(=C1F)I)F)F)N=NC1=C(C(=C(C(=C1F)F)I)F)F BFAKENXZKHGIGE-UHFFFAOYSA-N 0.000 description 4
- 229950005228 bromoform Drugs 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 4
- VGKZBAMIYUHSMU-UHFFFAOYSA-N 4-[[2-chloroethyl(nitroso)carbamoyl]amino]cyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(NC(=O)N(CCCl)N=O)CC1 VGKZBAMIYUHSMU-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000006345 epimerization reaction Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- MDIQXIJPQWLFSD-UHFFFAOYSA-N 3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(Br)Br)C1C(O)=O MDIQXIJPQWLFSD-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FKLJPTJMIBLJAV-UHFFFAOYSA-N Compound IV Chemical compound O1N=C(C)C=C1CCCCCCCOC1=CC=C(C=2OCCN=2)C=C1 FKLJPTJMIBLJAV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000009833 condensation Methods 0.000 description 2
- 230000005494 condensation Effects 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- AWGBKZRMLNVLAF-UHFFFAOYSA-N 3,5-dibromo-n,2-dihydroxybenzamide Chemical compound ONC(=O)C1=CC(Br)=CC(Br)=C1O AWGBKZRMLNVLAF-UHFFFAOYSA-N 0.000 description 1
- DSTFRXBZHUSPOE-UHFFFAOYSA-N 3-(2-chloro-2-fluoroethenyl)-2,2-dimethylcyclopropane-1-carboxylic acid Chemical compound CC1(C)C(C=C(F)Cl)C1C(O)=O DSTFRXBZHUSPOE-UHFFFAOYSA-N 0.000 description 1
- 102220470103 Amidophosphoribosyltransferase_C12F_mutation Human genes 0.000 description 1
- KSCBXCJUNGTAGU-UHFFFAOYSA-N C(=O)=[Pb] Chemical compound C(=O)=[Pb] KSCBXCJUNGTAGU-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 241000212342 Sium Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 229910001115 Zinc-copper couple Inorganic materials 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- TVZPLCNGKSPOJA-UHFFFAOYSA-N copper zinc Chemical compound [Cu].[Zn] TVZPLCNGKSPOJA-UHFFFAOYSA-N 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000950 dibromo group Chemical group Br* 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 description 1
- 229940099364 dichlorofluoromethane Drugs 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 238000005360 mashing Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/93—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems condensed with a ring other than six-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C62/00—Compounds having carboxyl groups bound to carbon atoms of rings other than six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C62/02—Saturated compounds containing hydroxy or O-metal groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7719612 | 1977-06-27 | ||
| FR7719612A FR2396006A1 (fr) | 1977-06-27 | 1977-06-27 | Nouveaux composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinyliques |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1249995A true CA1249995A (fr) | 1989-02-14 |
Family
ID=9192606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000306092A Expired CA1249995A (fr) | 1977-06-27 | 1978-06-23 | Composes a noyau cyclopropanique, procede de preparation et application a la preparation de derives cyclopropaniques a chaine dihalovinylique |
Country Status (17)
| Country | Link |
|---|---|
| US (3) | US4166063A (en, 2012) |
| JP (2) | JPS5412367A (en, 2012) |
| BE (1) | BE868445A (en, 2012) |
| CA (1) | CA1249995A (en, 2012) |
| CH (1) | CH632505A5 (en, 2012) |
| DE (1) | DE2827627A1 (en, 2012) |
| DK (2) | DK163828C (en, 2012) |
| ES (1) | ES471106A1 (en, 2012) |
| FR (1) | FR2396006A1 (en, 2012) |
| GB (1) | GB1600086A (en, 2012) |
| HU (1) | HU180061B (en, 2012) |
| IE (1) | IE46987B1 (en, 2012) |
| IT (1) | IT1105213B (en, 2012) |
| LU (1) | LU79871A1 (en, 2012) |
| NL (1) | NL189711C (en, 2012) |
| SE (2) | SE437661B (en, 2012) |
| SU (1) | SU1075970A3 (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4526987A (en) * | 1978-02-06 | 1985-07-02 | Fmc Corporation | Alkyl 6,6-dimethyl-2-oxo-3-oxabicyclo[3.1.0]hexane-1-carboxylates |
| JPS59172437A (ja) * | 1978-02-06 | 1984-09-29 | エフ・エム・シ−・コ−ポレイシヨン | ３−（２，２−ジハロビニル）−２，２−ジメチルシクロプロパンカルボン酸の製法 |
| FR2450830A1 (fr) * | 1978-07-24 | 1980-10-03 | Roussel Uclaf | Nouveau procede de preparation d'acides cyclopropane-1-carboxyliques 3-substitues |
| US4254282A (en) * | 1979-01-03 | 1981-03-03 | Fmc Corporation | Process for preparing cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acid |
| US4257956A (en) * | 1979-04-06 | 1981-03-24 | Shell Oil Company | Oxabicycloalkane pyrethroid intermediates |
| EP0029621A1 (en) * | 1979-11-01 | 1981-06-03 | Shell Internationale Researchmaatschappij B.V. | Iodo-lactones, a process for their preparation and their use in separating cis acids from cis/trans acids |
| US4237058A (en) * | 1979-11-01 | 1980-12-02 | Fmc Corporation | Bicyclic lactone derivatives |
| US4235780A (en) * | 1979-11-01 | 1980-11-25 | Fmc Corporation | Derivatives of 2H-pyran-2-one |
| DE3171470D1 (en) * | 1980-05-30 | 1985-08-29 | Shell Int Research | Process for the preparation of dihalomethylene-lactones |
| US4335253A (en) * | 1980-05-30 | 1982-06-15 | Shell Oil Company | Preparation of dihalovinyl compounds |
| CA1170663A (en) * | 1980-05-30 | 1984-07-10 | Petrus A. Kramer | Trihalomethylhydroxylactones and a process for their preparation |
| CA1167048A (en) * | 1980-10-22 | 1984-05-08 | Petrus A. Kramer | Cyclopropane derivatives, processes for their preparation and their use in the preparation of dihalovinylcyclopropane carboxylic acids |
| FR2607133B1 (fr) * | 1986-11-20 | 1989-05-05 | Roussel Uclaf | Nouveaux derives de l'acide 2,2-dimethyl cyclopropane carboxylique portant en 3 une chaine halogenee saturee, leur procede de preparation et leur application comme pesticides |
| FR2658820B1 (fr) * | 1990-02-27 | 1994-06-03 | Roussel Uclaf | Nouveaux derives du pyrrole, leur procede de preparation et leur application comme pesticides. |
| JPH0516558U (ja) * | 1991-08-19 | 1993-03-02 | 関東自動車工業株式会社 | 自動車の発進方向表示装置 |
| FR2683525B1 (fr) * | 1991-11-08 | 1994-01-21 | Roussel Uclaf | Nouveau procede de preparation de la lactone de l'acide 1r, cis 2,2-dimethyl 3-formyl cyclopropane-1-carboxylique et intermediaires . |
| FR2683526B1 (fr) * | 1991-11-08 | 1994-01-21 | Roussel Uclaf | Nouveau procede de preparation de la lactone de l'acide 1r, cis 2,2-dimethyl 3-formyl cyclopropane-1-carboxylique et intermediaires halogenes. |
| DK171797B1 (da) * | 1995-07-21 | 1997-06-02 | Cheminova Agro As | Cyclopropanderivater og fremgangsmåde til fremstilling af cyclopropancarboxylsyrer, ved hvilken disse cyclopropanderivater indgår som mellemprodukter. |
| DK174698B1 (da) * | 1998-02-18 | 2003-09-22 | Cheminova Agro As | Fremgangsmåde til fremstilling af cyclopropancarboxylsyrer |
| DE19954160A1 (de) * | 1999-11-10 | 2001-05-17 | Aventis Cropscience Gmbh | 5-Halo-4-fluor-4,7,7-trimethyl-3-oxabicyclo[4.1.0]heptan-2-one, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Herstellung von Cyclopropancarbonsäuren |
| WO2003087260A1 (en) * | 2002-04-05 | 2003-10-23 | University Of Massachusetts Lowell | Polymeric antioxidants |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1005722A (en) * | 1963-04-23 | 1965-09-29 | Sumitomo Chemical Co | Process for producing trans-chrysanthemic acid esters |
| SE386669B (sv) * | 1968-07-12 | 1976-08-16 | Roussel Uclaf | Sett att framstella inre hemiacylalen av cis-3,3-dimetyl-2-formylcyklopropan-1-karbonsyra |
| US4014918A (en) * | 1968-07-12 | 1977-03-29 | Roussel-Uclaf | Process for the preparation of cyclopropane derivatives and compounds produced therein |
| US3906026A (en) * | 1972-05-16 | 1975-09-16 | Sumitomo Chemical Co | Process for preparing alkyl trans-chrysanthemate |
| DE2326077C2 (de) | 1972-05-25 | 1985-12-12 | National Research Development Corp., London | Ungesättigte Cyclopropancarbonsäuren und deren Derivate, deren Herstellung und diese enthaltende Insektizide |
| JPS5011060A (en, 2012) * | 1973-05-10 | 1975-02-04 | ||
| IE41614B1 (en) * | 1973-08-15 | 1980-02-13 | Nat Res Dev | Substituted 2,2-dimethyl cylopropane carboxylic acid estersprocess for their preperation and their use as insecticides |
| US3989654A (en) * | 1973-11-22 | 1976-11-02 | Sumitomo Chemical Company, Limited | Process for preparing cis-chrysanthemic acid |
| JPS5850209B2 (ja) * | 1975-04-15 | 1983-11-09 | 住友化学工業株式会社 | ２ ２− ジメチル−３−（２ ２−ジハロビニル）−シクロプロパンカルボンサンユウドウタイノ セイゾウホウ |
| US4254282A (en) * | 1979-01-03 | 1981-03-03 | Fmc Corporation | Process for preparing cis-3-(2,2-dihalovinyl)-2,2-dimethylcyclopropanecarboxylic acid |
-
1977
- 1977-06-27 FR FR7719612A patent/FR2396006A1/fr active Granted
-
1978
- 1978-05-17 SE SE7805656A patent/SE437661B/sv not_active IP Right Cessation
- 1978-05-30 GB GB24216/78A patent/GB1600086A/en not_active Expired
- 1978-06-08 IE IE1168/78A patent/IE46987B1/en not_active IP Right Cessation
- 1978-06-09 SU SU782624348A patent/SU1075970A3/ru active
- 1978-06-12 US US05/914,399 patent/US4166063A/en not_active Expired - Lifetime
- 1978-06-15 IT IT49891/78A patent/IT1105213B/it active
- 1978-06-23 DE DE19782827627 patent/DE2827627A1/de active Granted
- 1978-06-23 CA CA000306092A patent/CA1249995A/fr not_active Expired
- 1978-06-23 CH CH690478A patent/CH632505A5/fr not_active IP Right Cessation
- 1978-06-26 JP JP7660278A patent/JPS5412367A/ja active Granted
- 1978-06-26 ES ES471106A patent/ES471106A1/es not_active Expired
- 1978-06-26 DK DK284978A patent/DK163828C/da not_active IP Right Cessation
- 1978-06-26 LU LU79871A patent/LU79871A1/xx unknown
- 1978-06-26 BE BE188830A patent/BE868445A/xx not_active IP Right Cessation
- 1978-06-26 HU HU78RO986A patent/HU180061B/hu unknown
- 1978-06-27 NL NLAANVRAGE7806915,A patent/NL189711C/xx not_active IP Right Cessation
-
1979
- 1979-04-06 US US06/027,654 patent/US4281182A/en not_active Expired - Lifetime
-
1981
- 1981-03-30 US US06/248,719 patent/US4513147A/en not_active Expired - Lifetime
-
1983
- 1983-03-24 SE SE8301635A patent/SE446723B/sv not_active IP Right Cessation
-
1986
- 1986-02-12 JP JP61027006A patent/JPS61218559A/ja active Granted
-
1990
- 1990-03-23 DK DK076890A patent/DK162225C/da not_active IP Right Cessation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |