ES2822673T3 - Procedimiento de ciclopropanación de olefinas con N-alquil-N-nitroso-compuestos - Google Patents
Procedimiento de ciclopropanación de olefinas con N-alquil-N-nitroso-compuestos Download PDFInfo
- Publication number
- ES2822673T3 ES2822673T3 ES14787207T ES14787207T ES2822673T3 ES 2822673 T3 ES2822673 T3 ES 2822673T3 ES 14787207 T ES14787207 T ES 14787207T ES 14787207 T ES14787207 T ES 14787207T ES 2822673 T3 ES2822673 T3 ES 2822673T3
- Authority
- ES
- Spain
- Prior art keywords
- nitroso
- alkyl
- compound
- process according
- carbon
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 52
- 230000008569 process Effects 0.000 title claims abstract description 44
- 150000001336 alkenes Chemical class 0.000 title claims description 52
- 238000005888 cyclopropanation reaction Methods 0.000 title description 37
- 239000000758 substrate Substances 0.000 claims abstract description 39
- 239000003054 catalyst Substances 0.000 claims abstract description 31
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 15
- 238000011065 in-situ storage Methods 0.000 claims abstract description 11
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 11
- 150000003624 transition metals Chemical class 0.000 claims abstract description 11
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000007363 ring formation reaction Methods 0.000 claims abstract description 5
- ZRKWMRDKSOPRRS-UHFFFAOYSA-N N-Methyl-N-nitrosourea Chemical compound O=NN(C)C(N)=O ZRKWMRDKSOPRRS-UHFFFAOYSA-N 0.000 claims description 74
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 54
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 claims description 47
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 42
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical group C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
- 238000006243 chemical reaction Methods 0.000 claims description 37
- 238000005191 phase separation Methods 0.000 claims description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 239000008346 aqueous phase Substances 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 21
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical group [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 20
- 239000007791 liquid phase Substances 0.000 claims description 19
- 239000003960 organic solvent Substances 0.000 claims description 19
- VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 claims description 16
- 239000007787 solid Substances 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 claims description 13
- JSNRRGGBADWTMC-UHFFFAOYSA-N (6E)-7,11-dimethyl-3-methylene-1,6,10-dodecatriene Chemical compound CC(C)=CCCC(C)=CCCC(=C)C=C JSNRRGGBADWTMC-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 11
- 239000012044 organic layer Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002585 base Substances 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical group CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 claims description 8
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- CXENHBSYCFFKJS-UHFFFAOYSA-N (3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene Natural products CC(C)=CCCC(C)=CCC=C(C)C=C CXENHBSYCFFKJS-UHFFFAOYSA-N 0.000 claims description 7
- 238000000926 separation method Methods 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 239000012455 biphasic mixture Substances 0.000 claims description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 5
- 229930009668 farnesene Natural products 0.000 claims description 5
- YBOCTGACBMJPDP-UHFFFAOYSA-N tert-butyl n-nitrosocarbamate Chemical compound CC(C)(C)OC(=O)NN=O YBOCTGACBMJPDP-UHFFFAOYSA-N 0.000 claims description 5
- 238000012546 transfer Methods 0.000 claims description 5
- 150000002170 ethers Chemical class 0.000 claims description 4
- 150000002576 ketones Chemical class 0.000 claims description 4
- MEJYDZQQVZJMPP-ULAWRXDQSA-N (3s,3ar,6r,6ar)-3,6-dimethoxy-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan Chemical compound CO[C@H]1CO[C@@H]2[C@H](OC)CO[C@@H]21 MEJYDZQQVZJMPP-ULAWRXDQSA-N 0.000 claims description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000007823 ocimene derivatives Chemical class 0.000 claims description 3
- XJPBRODHZKDRCB-UHFFFAOYSA-N trans-alpha-ocimene Natural products CC(=C)CCC=C(C)C=C XJPBRODHZKDRCB-UHFFFAOYSA-N 0.000 claims description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- FFKZOUIEAHOBHW-UHFFFAOYSA-N N,4-dimethyl-N-nitrosobenzenesulfonamide Chemical compound O=NN(C)S(=O)(=O)C1=CC=C(C)C=C1 FFKZOUIEAHOBHW-UHFFFAOYSA-N 0.000 claims description 2
- 101150003085 Pdcl gene Proteins 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000003973 alkyl amines Chemical class 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000003505 terpenes Chemical class 0.000 claims 1
- 239000012074 organic phase Substances 0.000 description 23
- 239000002904 solvent Substances 0.000 description 22
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000012071 phase Substances 0.000 description 15
- 238000002360 preparation method Methods 0.000 description 13
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 12
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- 150000004291 polyenes Chemical class 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 239000003205 fragrance Substances 0.000 description 8
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 7
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 7
- 239000004202 carbamide Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 108700039708 galantide Proteins 0.000 description 7
- 239000002243 precursor Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- 239000007789 gas Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- RXJQJOILAUBJEG-UHFFFAOYSA-N 1-cyclopropyl-3-methylbenzene Chemical compound CC1=CC=CC(C2CC2)=C1 RXJQJOILAUBJEG-UHFFFAOYSA-N 0.000 description 5
- 208000033962 Fontaine progeroid syndrome Diseases 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- -1 and NaNO 2 Chemical compound 0.000 description 5
- IPVIVOSBOUTTKM-UHFFFAOYSA-N ethyl 8-cyclopropyloctanoate Chemical compound CCOC(=O)CCCCCCCC1CC1 IPVIVOSBOUTTKM-UHFFFAOYSA-N 0.000 description 5
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- 238000005822 methylenation reaction Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000012258 stirred mixture Substances 0.000 description 5
- WVXAQUSBMRDRSY-UHFFFAOYSA-N 1-[1,2-dimethyl-4-(4-methylpent-3-enyl)cyclohex-3-en-1-yl]ethanone Chemical compound CC1C=C(CCC=C(C)C)CCC1(C)C(C)=O WVXAQUSBMRDRSY-UHFFFAOYSA-N 0.000 description 4
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 4
- 239000005977 Ethylene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 150000008049 diazo compounds Chemical class 0.000 description 4
- YIWFBNMYFYINAD-UHFFFAOYSA-N ethenylcyclopropane Chemical class C=CC1CC1 YIWFBNMYFYINAD-UHFFFAOYSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- MIRINVAHTDRKNC-UHFFFAOYSA-N 3-cyclopropyl-1-spiro[4.5]dec-9-en-9-ylpropan-1-one Chemical compound C1(CC1)CCC(=O)C1=CC2(CCCC2)CCC1 MIRINVAHTDRKNC-UHFFFAOYSA-N 0.000 description 3
- 102100031817 Delta-type opioid receptor Human genes 0.000 description 3
- 101100295829 Homo sapiens OPRD1 gene Proteins 0.000 description 3
- XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 3
- 101100244562 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) oprD gene Proteins 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001942 cyclopropanes Chemical class 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 3
- XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 235000000010 nanu Nutrition 0.000 description 3
- 244000082862 nanu Species 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 231100000331 toxic Toxicity 0.000 description 3
- 230000002588 toxic effect Effects 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- YQYKESUTYHZAGG-BZNIZROVSA-N 1-[(1r,2s)-1,2,8,8-tetramethyl-1,3,4,5,6,7-hexahydronaphthalen-2-yl]ethanone Chemical compound C1([C@H]([C@@](CC2)(C)C(C)=O)C)=C2CCCC1(C)C YQYKESUTYHZAGG-BZNIZROVSA-N 0.000 description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 238000005698 Diels-Alder reaction Methods 0.000 description 2
- ZFMSMUAANRJZFM-UHFFFAOYSA-N Estragole Chemical compound COC1=CC=C(CC=C)C=C1 ZFMSMUAANRJZFM-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- YMGUBTXCNDTFJI-UHFFFAOYSA-N cyclopropanecarboxylic acid Chemical compound OC(=O)C1CC1 YMGUBTXCNDTFJI-UHFFFAOYSA-N 0.000 description 2
- 150000008101 cyclopropylbenzenes Chemical class 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000011995 wilkinson's catalyst Substances 0.000 description 2
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- IHPKGUQCSIINRJ-NTMALXAHSA-N (Z)-beta-ocimene Chemical compound CC(C)=CC\C=C(\C)C=C IHPKGUQCSIINRJ-NTMALXAHSA-N 0.000 description 1
- OZXIZRZFGJZWBF-UHFFFAOYSA-N 1,3,5-trimethyl-2-(2,4,6-trimethylphenoxy)benzene Chemical compound CC1=CC(C)=CC(C)=C1OC1=C(C)C=C(C)C=C1C OZXIZRZFGJZWBF-UHFFFAOYSA-N 0.000 description 1
- LSWOCDLIYSKTRX-UHFFFAOYSA-N 1-butyl-1-nitrosourea Chemical compound CCCCN(N=O)C(N)=O LSWOCDLIYSKTRX-UHFFFAOYSA-N 0.000 description 1
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 description 1
- WPFFGMCNILGTEA-UHFFFAOYSA-N 1-spiro[4.5]dec-8-en-9-ylpent-4-en-1-one Chemical compound C1C(C(=O)CCC=C)=CCCC11CCCC1 WPFFGMCNILGTEA-UHFFFAOYSA-N 0.000 description 1
- JXBSHSBNOVLGHF-UHFFFAOYSA-N 10-cis-Dihydrofarnesen Natural products CC=C(C)CCC=C(C)CCC=C(C)C JXBSHSBNOVLGHF-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- 206010007269 Carcinogenicity Diseases 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102100034741 Cyclin-dependent kinase 20 Human genes 0.000 description 1
- 101500014379 Lymnaea stagnalis Ovulation hormone Proteins 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- FUSGACRLAFQQRL-UHFFFAOYSA-N N-Ethyl-N-nitrosourea Chemical compound CCN(N=O)C(N)=O FUSGACRLAFQQRL-UHFFFAOYSA-N 0.000 description 1
- 150000004008 N-nitroso compounds Chemical class 0.000 description 1
- HIKMTOIBEHOYSN-UHFFFAOYSA-N N-nitroso-N-prop-2-ynylacetamide Chemical compound CC(=O)N(CC#C)N=O HIKMTOIBEHOYSN-UHFFFAOYSA-N 0.000 description 1
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 1
- 239000005662 Paraffin oil Substances 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000489522 Ruscaceae Species 0.000 description 1
- 206010070835 Skin sensitisation Diseases 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001345 alkine derivatives Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052796 boron Chemical group 0.000 description 1
- CMUCDCNTKFCBJE-UHFFFAOYSA-N butan-2-yl N-methyl-N-nitrosocarbamate Chemical compound C(C)C(OC(N(C)N=O)=O)C CMUCDCNTKFCBJE-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 231100000260 carcinogenicity Toxicity 0.000 description 1
- 230000007670 carcinogenicity Effects 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000004205 dimethyl polysiloxane Substances 0.000 description 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- GNJARWZWODMTDR-UHFFFAOYSA-N ethyl dec-2-enoate Chemical compound CCCCCCCC=CC(=O)OCC GNJARWZWODMTDR-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000005111 flow chemistry technique Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 231100001261 hazardous Toxicity 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- SHOJXDKTYKFBRD-UHFFFAOYSA-N mesityl oxide Natural products CC(C)=CC(C)=O SHOJXDKTYKFBRD-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- SURZCVYFPAXNGN-UHFFFAOYSA-N methyl-carbamic acid ethyl ester Chemical compound CCOC(=O)NC SURZCVYFPAXNGN-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- DUNCVNHORHNONW-UHFFFAOYSA-N myrcenol Chemical compound CC(C)(O)CCCC(=C)C=C DUNCVNHORHNONW-UHFFFAOYSA-N 0.000 description 1
- 229930008383 myrcenol Natural products 0.000 description 1
- DWLVWMUCHSLGSU-UHFFFAOYSA-M n,n-dimethylcarbamate Chemical compound CN(C)C([O-])=O DWLVWMUCHSLGSU-UHFFFAOYSA-M 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- USFXMVDSQZKGGP-UHFFFAOYSA-N n-ethyl-n-(2-methyl-4-oxopentan-2-yl)nitrous amide Chemical compound CCN(N=O)C(C)(C)CC(C)=O USFXMVDSQZKGGP-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000001301 oxygen Chemical group 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 150000002940 palladium Chemical class 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 239000011833 salt mixture Substances 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 231100000370 skin sensitisation Toxicity 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JSNRRGGBADWTMC-NTCAYCPXSA-N trans-beta-farnesene Chemical compound CC(C)=CCC\C(C)=C\CCC(=C)C=C JSNRRGGBADWTMC-NTCAYCPXSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/02—Addition
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
- C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
- C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- B01J31/22—Organic complexes
- B01J31/2204—Organic complexes the ligands containing oxygen or sulfur as complexing atoms
- B01J31/2208—Oxygen, e.g. acetylacetonates
- B01J31/2213—At least two complexing oxygen atoms present in an at least bidentate or bridging ligand
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B37/00—Reactions without formation or introduction of functional groups containing hetero atoms, involving either the formation of a carbon-to-carbon bond between two carbon atoms not directly linked already or the disconnection of two directly linked carbon atoms
- C07B37/08—Isomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/86—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by condensation between a hydrocarbon and a non-hydrocarbon
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/30—Preparation of ethers by reactions not forming ether-oxygen bonds by increasing the number of carbon atoms, e.g. by oligomerisation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/69—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to carbon-to-carbon double or triple bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/553—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings polycyclic
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
- B01J2231/32—Addition reactions to C=C or C-C triple bonds
- B01J2231/324—Cyclisations via conversion of C-C multiple to single or less multiple bonds, e.g. cycloadditions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
- B01J2531/80—Complexes comprising metals of Group VIII as the central metal
- B01J2531/82—Metals of the platinum group
- B01J2531/824—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2531/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- C07C2531/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
- C07C2531/22—Organic complexes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/50—Spiro compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB1318886.7A GB201318886D0 (en) | 2013-10-25 | 2013-10-25 | Improvements i or relating to organic compounds |
| PCT/EP2014/072882 WO2015059290A1 (en) | 2013-10-25 | 2014-10-24 | Improvements in or relating to organic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2822673T3 true ES2822673T3 (es) | 2021-05-04 |
Family
ID=49767164
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES14787207T Active ES2822673T3 (es) | 2013-10-25 | 2014-10-24 | Procedimiento de ciclopropanación de olefinas con N-alquil-N-nitroso-compuestos |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US9718741B2 (cg-RX-API-DMAC10.html) |
| EP (1) | EP3060535B1 (cg-RX-API-DMAC10.html) |
| JP (1) | JP6585605B2 (cg-RX-API-DMAC10.html) |
| CN (1) | CN105658604B (cg-RX-API-DMAC10.html) |
| ES (1) | ES2822673T3 (cg-RX-API-DMAC10.html) |
| GB (1) | GB201318886D0 (cg-RX-API-DMAC10.html) |
| IL (1) | IL244929B (cg-RX-API-DMAC10.html) |
| MX (1) | MX381408B (cg-RX-API-DMAC10.html) |
| SG (1) | SG11201602725UA (cg-RX-API-DMAC10.html) |
| WO (1) | WO2015059290A1 (cg-RX-API-DMAC10.html) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB201507170D0 (en) | 2015-04-24 | 2015-06-10 | Givaudan Sa | Process |
| GB201507207D0 (en) | 2015-04-24 | 2015-06-10 | Givaudan Sa | Enzymes and applications thereof |
| GB201516396D0 (en) * | 2015-09-16 | 2015-10-28 | Givaudan Sa | Improvements in or relating to organic compounds |
| GB201618090D0 (en) | 2016-10-26 | 2016-12-07 | Givaudan Sa | Product |
| GB201720211D0 (en) * | 2017-12-05 | 2018-01-17 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN108484347B (zh) * | 2018-04-28 | 2021-02-05 | 江苏八巨药业有限公司 | 一种末端异戊二烯类化合物环丙烷化的制备方法 |
| GB201810514D0 (en) * | 2018-06-27 | 2018-08-15 | Givaudan Sa | Improvements in or relating to organic compounds |
| CN110577484A (zh) * | 2019-07-02 | 2019-12-17 | 凯莱英医药集团（天津）股份有限公司 | 环丙烷类化合物连续合成的方法及装置 |
| JP7441863B2 (ja) * | 2019-07-02 | 2024-03-01 | アシムケム ラボラトリーズ （ティエンジン） カンパニー リミテッド | シクロプロパン系化合物の連続合成方法及び装置 |
| CN111574411A (zh) * | 2020-04-24 | 2020-08-25 | 常州齐晖药业有限公司 | 一种地克珠利杂质b的制备方法 |
| CN111517991A (zh) * | 2020-04-24 | 2020-08-11 | 常州齐晖药业有限公司 | 一种地克珠利杂质a的制备方法 |
| CN113480404A (zh) * | 2021-06-30 | 2021-10-08 | 中昊(大连)化工研究设计院有限公司 | 一种环丙基溴合成的新方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650881A (en) | 1985-04-01 | 1987-03-17 | Iowa State University Research Foundation, Inc. | Synthesis of isocoumarins via thallation-olefination of arenes |
| JPS62129240A (ja) * | 1985-11-29 | 1987-06-11 | Tokyo Tanabe Co Ltd | ４′−シクロプロピルフエノン誘導体 |
| DE4327748B4 (de) * | 1993-08-18 | 2006-07-20 | Merck Patent Gmbh | Cyclopropyl- und Cyclobutyl-Derivate |
| JP3385264B2 (ja) * | 1995-04-11 | 2003-03-10 | 三井化学株式会社 | 置換チオフェン誘導体およびこれを有効成分とする農園芸用殺菌剤 |
| ES2157366T3 (es) * | 1995-06-09 | 2001-08-16 | Hoffmann La Roche | Derivados de pirimidindiona, pirimidintriona, triacindiona como antagonistas de receptores alfa-1-adrenergicos. |
| US5854405A (en) * | 1997-11-13 | 1998-12-29 | Aerojet-General Corporation | Continuous process for diazomethane from an n-methyl-n-nitrosoamine and from methylurea through n-methyl-n-nitrosourea |
| FR2801051B1 (fr) * | 1999-11-17 | 2001-12-14 | Adir | Nouveaux composes aminopyrroline, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| KR20110136901A (ko) * | 2004-02-24 | 2011-12-21 | 상꾜 가부시키가이샤 | 아미노 알코올 화합물 |
| EA201101085A1 (ru) * | 2005-12-22 | 2012-05-30 | ХАЙ ПОЙНТ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Феноксиуксусные кислоты в качестве активаторов ppar дельта |
| WO2010131145A1 (en) | 2009-05-12 | 2010-11-18 | Pfizer Limited | Cyclobutenedione derivatives |
| JP6086066B2 (ja) * | 2010-11-01 | 2017-03-01 | パセオン オーストリア ゲーエムベーハー ウント ツェーオー カーゲー | ジアゾ化合物の連続的な製造および反応 |
| WO2012075316A2 (en) * | 2010-12-01 | 2012-06-07 | Rigel Pharmaceuticals, Inc. | Cyclopropyl mida boronate |
| JP2014088326A (ja) * | 2011-02-22 | 2014-05-15 | Astellas Pharma Inc | ポリペプチド化合物 |
| US20120226041A1 (en) * | 2011-03-04 | 2012-09-06 | The Board Of Trustees Of The University Of Illinois | Catalysts and boronate esters |
| US9073924B2 (en) * | 2011-09-13 | 2015-07-07 | Glaxosmithkline Llc | Azaindazoles |
-
2013
- 2013-10-25 GB GBGB1318886.7A patent/GB201318886D0/en not_active Ceased
-
2014
- 2014-10-24 MX MX2016005053A patent/MX381408B/es unknown
- 2014-10-24 JP JP2016549636A patent/JP6585605B2/ja active Active
- 2014-10-24 CN CN201480058480.5A patent/CN105658604B/zh active Active
- 2014-10-24 ES ES14787207T patent/ES2822673T3/es active Active
- 2014-10-24 US US15/031,158 patent/US9718741B2/en active Active
- 2014-10-24 SG SG11201602725UA patent/SG11201602725UA/en unknown
- 2014-10-24 WO PCT/EP2014/072882 patent/WO2015059290A1/en not_active Ceased
- 2014-10-24 EP EP14787207.1A patent/EP3060535B1/en active Active
-
2016
- 2016-04-05 IL IL244929A patent/IL244929B/en active IP Right Grant
-
2017
- 2017-06-22 US US15/630,060 patent/US20170283342A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20160280615A1 (en) | 2016-09-29 |
| GB201318886D0 (en) | 2013-12-11 |
| IL244929A0 (en) | 2016-05-31 |
| WO2015059290A1 (en) | 2015-04-30 |
| MX2016005053A (es) | 2016-08-17 |
| IL244929B (en) | 2019-06-30 |
| EP3060535A1 (en) | 2016-08-31 |
| US9718741B2 (en) | 2017-08-01 |
| JP6585605B2 (ja) | 2019-10-02 |
| MX381408B (es) | 2025-03-12 |
| EP3060535B1 (en) | 2020-08-05 |
| JP2016538335A (ja) | 2016-12-08 |
| CN105658604B (zh) | 2019-10-25 |
| US20170283342A1 (en) | 2017-10-05 |
| CN105658604A (zh) | 2016-06-08 |
| SG11201602725UA (en) | 2016-05-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9718741B2 (en) | Organic compounds | |
| Glasnov et al. | Methylation using dimethylcarbonate catalysed by ionic liquids under continuous flow conditions | |
| Zhang et al. | Copper (II) triflate-catalyzed reduction of carboxylic acids to alcohols and reductive etherification of carbonyl compounds | |
| Dekamin et al. | An expeditious synthesis of cyanohydrin trimethylsilyl ethers using tetraethylammonium 2-(carbamoyl) benzoate as a bifunctional organocatalyst | |
| JP7330226B2 (ja) | Ｎ－メチル－ｎ－ニトロソ化合物を使用したオレフィンのシクロプロパン化のためのプロセス | |
| KR20210091773A (ko) | 칸나비디올의 연속 흐름 합성 | |
| MX2014012447A (es) | Proceso para la reduccion quimoselectiva de esteres carboxilicos terminalmente saturados. | |
| KR20220162884A (ko) | 시클로부탄테트라카르복실산 유도체의 제조 방법 | |
| RU2600741C2 (ru) | Способы получения 1,5,7-триазабицикло[4.4.0]-дец-5-eha по реакции дизамещённого карбодиимида и дипропилентриамина | |
| Song et al. | PEG400-enhanced synthesis of gem-dichloroaziridines and gem-dichlorocyclopropanes via in situ generated dichlorocarbene | |
| Zhang et al. | Transition-metal-free decarboxylation of dimethyl malonate: an efficient construction of α-amino acid esters using TBAI/TBHP | |
| Bandarenko et al. | Synthesis of raspberry and ginger ketones by nickel boride-catalyzed hydrogenation of 4-arylbut-3-en-2-ones | |
| Zhang et al. | Indium (III) mediated Markovnikov addition of malonates and β-ketoesters to terminal alkynes and the formation of Knoevenagel condensation products | |
| Bernal et al. | Synthesis of novel β-functionalized α-oximinoketones via hetero-Michael addition of alcohols and mercaptans to enones | |
| Popov et al. | Condensation of adamantanone with methylene-active compounds | |
| Muratov et al. | Formal reductive addition of acetonitrile to aldehydes and ketones | |
| Vilas et al. | A mild and efficient way to prepare ε-caprolactam by using a novel salt related with ionic liquids | |
| Yu et al. | Selective Oxidation of Sulfides to Sulfoxides with Tert-Butylnitrite as an Alternative Oxidant | |
| JP2017149687A (ja) | Ｏ−ベンゼンスルホニル−アセトヒドロキサム酸エステル誘導体およびニトリル化合物の製造方法 | |
| ES2454617T3 (es) | Procedimiento de producción de derivados de cicloalcanonas | |
| BR112016008531B1 (pt) | Aperfeiçoamentos em ou relacionados a compostos orgânicos | |
| RU2443672C1 (ru) | Способ получения 1-фенокси-2,2-дихлорциклопропана | |
| Qandalee et al. | Synthesis of polyfunctionalized amino furans with long conjugated aromatic systems using nucleophilic aromatic isocyanide | |
| RU2263661C1 (ru) | Способ получения 1-м-феноксифенил-2-нитроалкенов | |
| RU2240303C1 (ru) | Способ получения альфа-адамантилсодержащих альдегидов |