CA2082574C - 3-isoxazolylphenyl compounds, their preparation and their use - Google Patents

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Publication number

CA2082574C

CA2082574C CA002082574A CA2082574A CA2082574C CA 2082574 C CA2082574 C CA 2082574C CA 002082574 A CA002082574 A CA 002082574A CA 2082574 A CA2082574 A CA 2082574A CA 2082574 C CA2082574 C CA 2082574C

Authority

CA

Canada

Prior art keywords

formula

alkyl

compound

methyl

och

Prior art date

1991-11-18

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 - Fee Related

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• -1 3-isoxazolylphenyl compounds Chemical class 0.000 title claims abstract description 224
• 238000002360 preparation method Methods 0.000 title claims abstract description 33
• 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 76
• 238000000034 method Methods 0.000 claims abstract description 59
• 230000008569 process Effects 0.000 claims abstract description 50
• 239000001257 hydrogen Substances 0.000 claims abstract description 32
• 125000005843 halogen group Chemical group 0.000 claims abstract description 27
• 229910052736 halogen Inorganic materials 0.000 claims abstract description 20
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 16
• 125000003118 aryl group Chemical group 0.000 claims abstract description 13
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 12
• 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 12
• 150000002431 hydrogen Chemical group 0.000 claims abstract description 11
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
• 125000004076 pyridyl group Chemical group 0.000 claims abstract description 9
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
• 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 5
• 125000001624 naphthyl group Chemical group 0.000 claims abstract description 5
• 150000001875 compounds Chemical class 0.000 claims description 81
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 30
• 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 27
• 229910000077 silane Inorganic materials 0.000 claims description 25
• 150000003254 radicals Chemical class 0.000 claims description 24
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 23
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
• 239000003960 organic solvent Substances 0.000 claims description 23
• BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 22
• 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 19
• 150000002367 halogens Chemical group 0.000 claims description 18
• 150000001340 alkali metals Chemical class 0.000 claims description 17
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
• 229910001413 alkali metal ion Inorganic materials 0.000 claims description 12
• 229910001420 alkaline earth metal ion Inorganic materials 0.000 claims description 12
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 9
• 241000607479 Yersinia pestis Species 0.000 claims description 9
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
• 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
• 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 5
• 239000001301 oxygen Substances 0.000 claims description 5
• 229920006395 saturated elastomer Polymers 0.000 claims description 5
• 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
• 125000004122 cyclic group Chemical group 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
• 125000005842 heteroatom Chemical group 0.000 claims description 3
• 239000000575 pesticide Substances 0.000 claims description 3
• 239000011593 sulfur Substances 0.000 claims description 3
• SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
• 239000000654 additive Substances 0.000 claims description 2
• 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
• 125000000217 alkyl group Chemical group 0.000 abstract description 11
• 239000003795 chemical substances by application Substances 0.000 abstract description 9
• 125000003342 alkenyl group Chemical group 0.000 abstract description 6
• 125000000753 cycloalkyl group Chemical group 0.000 abstract description 6
• 125000000304 alkynyl group Chemical group 0.000 abstract description 5
• 125000003545 alkoxy group Chemical group 0.000 abstract description 2
• 125000000262 haloalkenyl group Chemical group 0.000 abstract description 2
• 125000004438 haloalkoxy group Chemical group 0.000 abstract description 2
• 125000001188 haloalkyl group Chemical group 0.000 abstract description 2
• 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
• 125000002947 alkylene group Chemical group 0.000 abstract 1
• 239000000460 chlorine Substances 0.000 description 172
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 117
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 78
• 238000006243 chemical reaction Methods 0.000 description 55
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 54
• 239000000243 solution Substances 0.000 description 44
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 39
• 239000000203 mixture Substances 0.000 description 35
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 34
• 229910052801 chlorine Inorganic materials 0.000 description 34
• 229910052799 carbon Inorganic materials 0.000 description 30
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 29
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 27
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
• 229910052794 bromium Inorganic materials 0.000 description 25
• 239000004480 active ingredient Substances 0.000 description 23
• 125000001424 substituent group Chemical group 0.000 description 23
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 21
• 239000011737 fluorine Substances 0.000 description 21
• 229910052731 fluorine Inorganic materials 0.000 description 21
• 235000019000 fluorine Nutrition 0.000 description 21
• 229940060037 fluorine Drugs 0.000 description 21
• 229910052751 metal Inorganic materials 0.000 description 21
• 239000002184 metal Substances 0.000 description 21
• 239000002904 solvent Substances 0.000 description 20
• 239000007858 starting material Substances 0.000 description 20
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 18
• 101150041968 CDC13 gene Proteins 0.000 description 18
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 18
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 18
• 239000000741 silica gel Substances 0.000 description 18
• 229910002027 silica gel Inorganic materials 0.000 description 18
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 17
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 16
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 16
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 16
• MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 16
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 15
• 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 15
• 238000003756 stirring Methods 0.000 description 15
• URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 14
• RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 14
• IVSZLXZYQVIEFR-UHFFFAOYSA-N m-xylene Chemical compound CC1=CC=CC(C)=C1 IVSZLXZYQVIEFR-UHFFFAOYSA-N 0.000 description 14
• 229910052744 lithium Inorganic materials 0.000 description 13
• 239000012074 organic phase Substances 0.000 description 13
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 13
• 239000011734 sodium Substances 0.000 description 13
• 229910052708 sodium Inorganic materials 0.000 description 13
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 12
• 239000011541 reaction mixture Substances 0.000 description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 12
• 229910052783 alkali metal Inorganic materials 0.000 description 11
• 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 11
• 239000003921 oil Substances 0.000 description 11
• 229910052700 potassium Inorganic materials 0.000 description 11
• FIARMZDBEGVMLV-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanolate Chemical group [O-]C(F)(F)C(F)(F)F FIARMZDBEGVMLV-UHFFFAOYSA-N 0.000 description 10
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
• 239000002585 base Substances 0.000 description 10
• 239000003054 catalyst Substances 0.000 description 10
• 125000000842 isoxazolyl group Chemical group 0.000 description 10
• 229940073584 methylene chloride Drugs 0.000 description 10
• 150000002825 nitriles Chemical class 0.000 description 10
• 238000005160 1H NMR spectroscopy Methods 0.000 description 9
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 9
• 230000015572 biosynthetic process Effects 0.000 description 9
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 9
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
• 239000011777 magnesium Substances 0.000 description 9
• 239000012071 phase Substances 0.000 description 9
• 238000000746 purification Methods 0.000 description 9
• 238000003786 synthesis reaction Methods 0.000 description 9
• IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 8
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
• 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
• 238000004440 column chromatography Methods 0.000 description 8
• 229910052740 iodine Inorganic materials 0.000 description 8
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 8
• 238000012986 modification Methods 0.000 description 8
• 230000004048 modification Effects 0.000 description 8
• 239000003208 petroleum Substances 0.000 description 8
• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
• 239000007787 solid Substances 0.000 description 8
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
• ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 7
• 239000002253 acid Substances 0.000 description 7
• 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 7
• 150000002170 ethers Chemical class 0.000 description 7
• 150000005826 halohydrocarbons Chemical class 0.000 description 7
• UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 7
• 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 7
• 239000000843 powder Substances 0.000 description 7
• 239000000047 product Substances 0.000 description 7
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 7
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 7
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
• 125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 6
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 6
• 125000004781 2,2-dichloro-2-fluoroethyl group Chemical group [H]C([H])(*)C(F)(Cl)Cl 0.000 description 6
• ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
• 125000004780 2-chloro-2,2-difluoroethyl group Chemical group [H]C([H])(*)C(F)(F)Cl 0.000 description 6
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 6
• WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
• 235000019445 benzyl alcohol Nutrition 0.000 description 6
• 150000003938 benzyl alcohols Chemical class 0.000 description 6
• 125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 6
• JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
• 125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 description 6
• 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 description 6
• 239000006185 dispersion Substances 0.000 description 6
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 6
• 238000009472 formulation Methods 0.000 description 6
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 6
• LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
• DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 6
• 125000001190 organyl group Chemical group 0.000 description 6
• 230000036647 reaction Effects 0.000 description 6
• 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 6
• 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 description 5
• 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 description 5
• 125000004779 2-chloro-2-fluoroethyl group Chemical group [H]C([H])(*)C([H])(F)Cl 0.000 description 5
• DUNULJXPOJZNHM-UHFFFAOYSA-N 2-methyl-3-(oxan-2-yloxymethyl)benzaldehyde Chemical compound C1=CC=C(C=O)C(C)=C1COC1OCCCC1 DUNULJXPOJZNHM-UHFFFAOYSA-N 0.000 description 5
• 125000004773 chlorofluoromethyl group Chemical group [H]C(F)(Cl)* 0.000 description 5
• 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 5
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
• 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 description 5
• 238000004821 distillation Methods 0.000 description 5
• 239000000839 emulsion Substances 0.000 description 5
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 5
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 5
• 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 5
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 5
• 229910000104 sodium hydride Inorganic materials 0.000 description 5
• 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 description 5
• FEWLNYSYJNLUOO-UHFFFAOYSA-N 1-Piperidinecarboxaldehyde Chemical compound O=CN1CCCCC1 FEWLNYSYJNLUOO-UHFFFAOYSA-N 0.000 description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
• WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
• LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
• 241000244206 Nematoda Species 0.000 description 4
• KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
• DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
• 230000009471 action Effects 0.000 description 4
• 150000001299 aldehydes Chemical class 0.000 description 4
• 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
• HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
• 239000004359 castor oil Substances 0.000 description 4
• 235000019438 castor oil Nutrition 0.000 description 4
• 238000004587 chromatography analysis Methods 0.000 description 4
• 238000001816 cooling Methods 0.000 description 4
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
• 238000001035 drying Methods 0.000 description 4
• 238000010410 dusting Methods 0.000 description 4
• ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 4
• 239000011261 inert gas Substances 0.000 description 4
• ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
• 229910052749 magnesium Inorganic materials 0.000 description 4
• 150000002739 metals Chemical class 0.000 description 4
• 150000002902 organometallic compounds Chemical class 0.000 description 4
• 239000007800 oxidant agent Substances 0.000 description 4
• 150000002923 oximes Chemical class 0.000 description 4
• FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 4
• NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 4
• 229910000105 potassium hydride Inorganic materials 0.000 description 4
• 125000006239 protecting group Chemical group 0.000 description 4
• 239000012312 sodium hydride Substances 0.000 description 4
• 239000000725 suspension Substances 0.000 description 4
• 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 4
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