DE2554790A1 - Tetrasubstituierte zinnorganische verbindungen - Google Patents

Info

Publication number

DE2554790A1

DE2554790A1 DE19752554790 DE2554790A DE2554790A1 DE 2554790 A1 DE2554790 A1 DE 2554790A1 DE 19752554790 DE19752554790 DE 19752554790 DE 2554790 A DE2554790 A DE 2554790A DE 2554790 A1 DE2554790 A1 DE 2554790A1

Authority

DE

Germany

Prior art keywords

carbon atoms

straight

branched alkyl

hydrogen

chain

Prior art date

1974-12-26

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.)

Pending

Links

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• 150000003606 tin compounds Chemical class 0.000 title description 6
• -1 nitro, acetyl Chemical group 0.000 claims description 156
• 150000001875 compounds Chemical class 0.000 claims description 145
• 125000004432 carbon atom Chemical group C* 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 61
• 239000011734 sodium Substances 0.000 claims description 54
• 229910052708 sodium Inorganic materials 0.000 claims description 54
• 241000196324 Embryophyta Species 0.000 claims description 45
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 claims description 39
• 229910052739 hydrogen Inorganic materials 0.000 claims description 38
• 239000001257 hydrogen Substances 0.000 claims description 37
• 238000000034 method Methods 0.000 claims description 37
• 229910052757 nitrogen Inorganic materials 0.000 claims description 35
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
• 125000003118 aryl group Chemical group 0.000 claims description 23
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 21
• ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 19
• 239000011591 potassium Substances 0.000 claims description 18
• 229910052700 potassium Inorganic materials 0.000 claims description 18
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 17
• 238000006243 chemical reaction Methods 0.000 claims description 17
• 150000002431 hydrogen Chemical class 0.000 claims description 17
• 150000002367 halogens Chemical class 0.000 claims description 14
• 125000003545 alkoxy group Chemical group 0.000 claims description 13
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
• 239000002904 solvent Substances 0.000 claims description 13
• 241000238631 Hexapoda Species 0.000 claims description 12
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 11
• 239000005977 Ethylene Substances 0.000 claims description 11
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 11
• 125000001624 naphthyl group Chemical group 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
• 229910052736 halogen Inorganic materials 0.000 claims description 8
• 229910052744 lithium Inorganic materials 0.000 claims description 8
• WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 7
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
• 125000002947 alkylene group Chemical group 0.000 claims description 6
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 6
• 239000011521 glass Substances 0.000 claims description 6
• 150000004678 hydrides Chemical class 0.000 claims description 6
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
• 125000003342 alkenyl group Chemical group 0.000 claims description 5
• 125000004414 alkyl thio group Chemical group 0.000 claims description 5
• 201000010099 disease Diseases 0.000 claims description 5
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
• QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims description 5
• 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
• 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
• 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
• 125000002877 alkyl aryl group Chemical group 0.000 claims description 4
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
• VDYIOWXZMNKCHN-UHFFFAOYSA-N ethyl(trimethyl)stannane Chemical compound CC[Sn](C)(C)C VDYIOWXZMNKCHN-UHFFFAOYSA-N 0.000 claims description 4
• 125000003106 haloaryl group Chemical group 0.000 claims description 4
• 230000008569 process Effects 0.000 claims description 4
• 239000003054 catalyst Substances 0.000 claims description 3
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
• 241000256113 Culicidae Species 0.000 claims description 2
• 125000005036 alkoxyphenyl group Chemical group 0.000 claims description 2
• 239000012298 atmosphere Substances 0.000 claims description 2
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
• 229910052794 bromium Inorganic materials 0.000 claims description 2
• 230000008859 change Effects 0.000 claims description 2
• 239000000460 chlorine Substances 0.000 claims description 2
• 229910052801 chlorine Inorganic materials 0.000 claims description 2
• 125000001188 haloalkyl group Chemical group 0.000 claims description 2
• 125000005059 halophenyl group Chemical group 0.000 claims description 2
• 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 2
• 125000001424 substituent group Chemical group 0.000 claims description 2
• LJTSJFRSRPUQBO-UHFFFAOYSA-N 1-(3-iodopropyl)piperidine Chemical compound ICCCN1CCCCC1 LJTSJFRSRPUQBO-UHFFFAOYSA-N 0.000 claims 1
• OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 claims 1
• QBJAVKBBTBUBSA-UHFFFAOYSA-N 2-dodecoxyethyl(trimethyl)stannane Chemical compound CCCCCCCCCCCCOCC[Sn](C)(C)C QBJAVKBBTBUBSA-UHFFFAOYSA-N 0.000 claims 1
• KGBKXPHTGXXMBB-UHFFFAOYSA-N 3-trimethylstannyl-n-[(3-trimethylstannylpropanoylamino)methyl]propanamide Chemical compound C[Sn](C)(C)CCC(=O)NCNC(=O)CC[Sn](C)(C)C KGBKXPHTGXXMBB-UHFFFAOYSA-N 0.000 claims 1
• 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims 1
• PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 1
• HMJQOLXJRJTWPL-UHFFFAOYSA-N trimethyl(3-phenylsulfanylpropyl)stannane Chemical compound C[Sn](C)(C)CCCSC1=CC=CC=C1 HMJQOLXJRJTWPL-UHFFFAOYSA-N 0.000 claims 1
• NDFOWEMRBOAGLS-UHFFFAOYSA-N trimethyl-[2-(6-methylpyridin-3-yl)ethyl]stannane Chemical compound CC1=CC=C(CC[Sn](C)(C)C)C=N1 NDFOWEMRBOAGLS-UHFFFAOYSA-N 0.000 claims 1
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
• 238000004821 distillation Methods 0.000 description 62
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 54
• 238000012360 testing method Methods 0.000 description 42
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 32
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 31
• 239000003921 oil Substances 0.000 description 31
• 235000019198 oils Nutrition 0.000 description 31
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
• 239000007787 solid Substances 0.000 description 25
• 239000000243 solution Substances 0.000 description 25
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
• AFOSIXZFDONLBT-UHFFFAOYSA-N divinyl sulfone Chemical compound C=CS(=O)(=O)C=C AFOSIXZFDONLBT-UHFFFAOYSA-N 0.000 description 24
• 239000000203 mixture Substances 0.000 description 24
• UKHQRARQNZOXRL-UHFFFAOYSA-N trimethyltin Chemical compound C[SnH](C)C UKHQRARQNZOXRL-UHFFFAOYSA-N 0.000 description 24
• 229920000742 Cotton Polymers 0.000 description 21
• 239000004009 herbicide Substances 0.000 description 21
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 20
• 241001124076 Aphididae Species 0.000 description 19
• 241000219146 Gossypium Species 0.000 description 19
• 230000033228 biological regulation Effects 0.000 description 19
• 241000238876 Acari Species 0.000 description 17
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 17
• 239000000047 product Substances 0.000 description 16
• 241000254173 Coleoptera Species 0.000 description 15
• 230000009102 absorption Effects 0.000 description 15
• 238000010521 absorption reaction Methods 0.000 description 15
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• 239000011541 reaction mixture Substances 0.000 description 15
• 239000000126 substance Substances 0.000 description 15
• 150000003457 sulfones Chemical class 0.000 description 15
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 14
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• 238000004140 cleaning Methods 0.000 description 12
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• 240000008853 Datura stramonium Species 0.000 description 10
• 239000007810 chemical reaction solvent Substances 0.000 description 10
• 241000208125 Nicotiana Species 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 210000003608 fece Anatomy 0.000 description 9
• 239000007858 starting material Substances 0.000 description 9
• 241000255925 Diptera Species 0.000 description 8
• 238000005481 NMR spectroscopy Methods 0.000 description 8
• 244000062793 Sorghum vulgare Species 0.000 description 8
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• 230000037406 food intake Effects 0.000 description 8
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• 235000019713 millet Nutrition 0.000 description 8
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• 229910052718 tin Inorganic materials 0.000 description 8
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
• 235000000208 Solanum incanum Nutrition 0.000 description 7
• ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical group [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 7
• 238000009835 boiling Methods 0.000 description 7
• 239000012876 carrier material Substances 0.000 description 7
• 239000002917 insecticide Substances 0.000 description 7
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 7
• 239000003208 petroleum Substances 0.000 description 7
• 235000013311 vegetables Nutrition 0.000 description 7
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
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• CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 4
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• 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
• 230000000704 physical effect Effects 0.000 description 1
• 239000002985 plastic film Substances 0.000 description 1
• 229920006255 plastic film Polymers 0.000 description 1
• 229920000642 polymer Polymers 0.000 description 1
• 229920001296 polysiloxane Polymers 0.000 description 1
• AIVGEFNWJBSEQR-UHFFFAOYSA-M potassium;(4-butylphenyl)-oxido-sulfanylidene-$l^{4}-sulfane Chemical compound [K+].CCCCC1=CC=C(S([O-])=S)C=C1 AIVGEFNWJBSEQR-UHFFFAOYSA-M 0.000 description 1
• ZPNNHRKFDLRIQR-UHFFFAOYSA-M potassium;(4-methylphenyl)-oxido-sulfanylidene-$l^{4}-sulfane Chemical compound [K+].CC1=CC=C(S([O-])=S)C=C1 ZPNNHRKFDLRIQR-UHFFFAOYSA-M 0.000 description 1
• WIWPZEAUKJVRGT-UHFFFAOYSA-M potassium;2,4,5-trichlorobenzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC(Cl)=C(Cl)C=C1Cl WIWPZEAUKJVRGT-UHFFFAOYSA-M 0.000 description 1
• XHDHCCRWRGDQOP-UHFFFAOYSA-M potassium;2,5-di(propan-2-yl)benzenesulfinate Chemical compound [K+].CC(C)C1=CC=C(C(C)C)C(S([O-])=O)=C1 XHDHCCRWRGDQOP-UHFFFAOYSA-M 0.000 description 1
• FZFNEMVXYNSHGP-UHFFFAOYSA-M potassium;2,5-dichlorobenzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC(Cl)=CC=C1Cl FZFNEMVXYNSHGP-UHFFFAOYSA-M 0.000 description 1
• AUWJDJBXDXOBNM-UHFFFAOYSA-M potassium;2-bromo-4-methoxybenzenesulfinate Chemical compound [K+].COC1=CC=C(S([O-])=O)C(Br)=C1 AUWJDJBXDXOBNM-UHFFFAOYSA-M 0.000 description 1
• MIDOSZGIPYRXCH-UHFFFAOYSA-M potassium;2-methoxy-5-nitrobenzenesulfinate Chemical compound [K+].COC1=CC=C([N+]([O-])=O)C=C1S([O-])=O MIDOSZGIPYRXCH-UHFFFAOYSA-M 0.000 description 1
• SYQNEGAYCHGKRZ-UHFFFAOYSA-M potassium;3,4-dimethoxybenzenesulfinate Chemical compound [K+].COC1=CC=C(S([O-])=O)C=C1OC SYQNEGAYCHGKRZ-UHFFFAOYSA-M 0.000 description 1
• MOYXJRKRIAGYRK-UHFFFAOYSA-M potassium;3,5-dichloro-2-hydroxybenzenesulfinate Chemical compound [K+].OC1=C(Cl)C=C(Cl)C=C1S([O-])=O MOYXJRKRIAGYRK-UHFFFAOYSA-M 0.000 description 1
• QFCUZAJBJXJMON-UHFFFAOYSA-M potassium;3-nitrobenzenesulfinate Chemical compound [K+].[O-][N+](=O)C1=CC=CC(S([O-])=O)=C1 QFCUZAJBJXJMON-UHFFFAOYSA-M 0.000 description 1
• UKYAWXXEFVGGED-UHFFFAOYSA-M potassium;3-nitrophenolate Chemical compound [K+].[O-]C1=CC=CC([N+]([O-])=O)=C1 UKYAWXXEFVGGED-UHFFFAOYSA-M 0.000 description 1
• XHOCJRLIOGGOKP-UHFFFAOYSA-M potassium;4-acetylphenolate Chemical compound [K+].CC(=O)C1=CC=C([O-])C=C1 XHOCJRLIOGGOKP-UHFFFAOYSA-M 0.000 description 1
• LPBQKKVXLRZPEV-UHFFFAOYSA-M potassium;4-butoxybenzenesulfinate Chemical compound [K+].CCCCOC1=CC=C(S([O-])=O)C=C1 LPBQKKVXLRZPEV-UHFFFAOYSA-M 0.000 description 1
• KQZLTJGDWZAZPQ-UHFFFAOYSA-M potassium;4-chlorobenzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=C(Cl)C=C1 KQZLTJGDWZAZPQ-UHFFFAOYSA-M 0.000 description 1
• PUKDGBKVHVQAJP-UHFFFAOYSA-M potassium;4-ethoxybenzenesulfinate Chemical compound [K+].CCOC1=CC=C(S([O-])=O)C=C1 PUKDGBKVHVQAJP-UHFFFAOYSA-M 0.000 description 1
• RWBYKGVRTNEMAM-UHFFFAOYSA-M potassium;4-methoxy-2-methylbenzenesulfinate Chemical compound [K+].COC1=CC=C(S([O-])=O)C(C)=C1 RWBYKGVRTNEMAM-UHFFFAOYSA-M 0.000 description 1
• GNLWYSKKSGTQLQ-UHFFFAOYSA-M potassium;4-methoxybenzenesulfinate Chemical compound [K+].COC1=CC=C(S([O-])=O)C=C1 GNLWYSKKSGTQLQ-UHFFFAOYSA-M 0.000 description 1
• DXKOILALGOFJCV-UHFFFAOYSA-M potassium;5-chloro-2-methoxybenzenesulfinate Chemical compound [K+].COC1=CC=C(Cl)C=C1S([O-])=O DXKOILALGOFJCV-UHFFFAOYSA-M 0.000 description 1
• YWGWWIKGZSFMPZ-UHFFFAOYSA-M potassium;5-chloro-2-methylphenolate Chemical compound [K+].CC1=CC=C(Cl)C=C1[O-] YWGWWIKGZSFMPZ-UHFFFAOYSA-M 0.000 description 1
• GUMLDYISXPRHIW-UHFFFAOYSA-M potassium;ethanesulfinate Chemical compound [K+].CCS([O-])=O GUMLDYISXPRHIW-UHFFFAOYSA-M 0.000 description 1
• AUWSPGWDMSKOTA-UHFFFAOYSA-M potassium;naphthalene-2-sulfinate Chemical compound [K+].C1=CC=CC2=CC(S(=O)[O-])=CC=C21 AUWSPGWDMSKOTA-UHFFFAOYSA-M 0.000 description 1
• PGUGFTNEIHYPHF-UHFFFAOYSA-M potassium;propane-1-sulfinate Chemical compound [K+].CCCS([O-])=O PGUGFTNEIHYPHF-UHFFFAOYSA-M 0.000 description 1
• 239000000843 powder Substances 0.000 description 1
• 239000002244 precipitate Substances 0.000 description 1
• 238000001556 precipitation Methods 0.000 description 1
• 239000003755 preservative agent Substances 0.000 description 1
• 238000003825 pressing Methods 0.000 description 1
• FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
• PPNNVWQGVFZHNA-UHFFFAOYSA-N prop-2-enylsulfanylcyclohexane Chemical compound C=CCSC1CCCCC1 PPNNVWQGVFZHNA-UHFFFAOYSA-N 0.000 description 1
• JEJKPKFDMNNGDH-UHFFFAOYSA-N prop-2-enylsulfanylmethylbenzene Chemical compound C=CCSCC1=CC=CC=C1 JEJKPKFDMNNGDH-UHFFFAOYSA-N 0.000 description 1
• BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
• LUQVWCUAYBJIKP-UHFFFAOYSA-N propan-2-yl dec-9-enoate Chemical compound CC(C)OC(=O)CCCCCCCC=C LUQVWCUAYBJIKP-UHFFFAOYSA-N 0.000 description 1
• LYBIZMNPXTXVMV-UHFFFAOYSA-N propan-2-yl prop-2-enoate Chemical compound CC(C)OC(=O)C=C LYBIZMNPXTXVMV-UHFFFAOYSA-N 0.000 description 1
• PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 150000003222 pyridines Chemical class 0.000 description 1
• 230000035484 reaction time Effects 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 150000003839 salts Chemical class 0.000 description 1
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• 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
• 230000003248 secreting effect Effects 0.000 description 1
• 238000000926 separation method Methods 0.000 description 1
• 150000004756 silanes Chemical class 0.000 description 1
• 238000001577 simple distillation Methods 0.000 description 1
• 231100000438 skin toxicity Toxicity 0.000 description 1
• 238000002791 soaking Methods 0.000 description 1
• 235000002639 sodium chloride Nutrition 0.000 description 1
• QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
• HJHVQCXHVMGZNC-JCJNLNMISA-M sodium;(2z)-2-[(3r,4s,5s,8s,9s,10s,11r,13r,14s,16s)-16-acetyloxy-3,11-dihydroxy-4,8,10,14-tetramethyl-2,3,4,5,6,7,9,11,12,13,15,16-dodecahydro-1h-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoate Chemical compound [Na+].O[C@@H]([C@@H]12)C[C@H]3\C(=C(/CCC=C(C)C)C([O-])=O)[C@@H](OC(C)=O)C[C@]3(C)[C@@]2(C)CC[C@@H]2[C@]1(C)CC[C@@H](O)[C@H]2C HJHVQCXHVMGZNC-JCJNLNMISA-M 0.000 description 1
• FTSCGYRCOWFJRO-UHFFFAOYSA-M sodium;2,4-dimethylbenzenesulfinate Chemical compound [Na+].CC1=CC=C(S([O-])=O)C(C)=C1 FTSCGYRCOWFJRO-UHFFFAOYSA-M 0.000 description 1
• LNXOEMYJXPAQGJ-UHFFFAOYSA-M sodium;4-hexylbenzenesulfinate Chemical compound [Na+].CCCCCCC1=CC=C(S([O-])=O)C=C1 LNXOEMYJXPAQGJ-UHFFFAOYSA-M 0.000 description 1
• CSZRTTCJJXGZBQ-UHFFFAOYSA-M sodium;4-octylbenzenesulfinate Chemical compound [Na+].CCCCCCCCC1=CC=C(S([O-])=O)C=C1 CSZRTTCJJXGZBQ-UHFFFAOYSA-M 0.000 description 1
• YZFJQTYHGXQSTN-UHFFFAOYSA-M sodium;4-propylbenzenesulfinate Chemical compound [Na+].CCCC1=CC=C(S([O-])=O)C=C1 YZFJQTYHGXQSTN-UHFFFAOYSA-M 0.000 description 1
• IHMVILRIAKQYIY-UHFFFAOYSA-M sodium;4-tert-butylbenzenesulfinate Chemical compound [Na+].CC(C)(C)C1=CC=C(S([O-])=O)C=C1 IHMVILRIAKQYIY-UHFFFAOYSA-M 0.000 description 1
• CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
• RZWQDAUIUBVCDD-UHFFFAOYSA-M sodium;benzenethiolate Chemical compound [Na+].[S-]C1=CC=CC=C1 RZWQDAUIUBVCDD-UHFFFAOYSA-M 0.000 description 1
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• ZNKMIWQRYUNHQO-UHFFFAOYSA-N tributoxy(hex-5-enyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)CCCCC=C ZNKMIWQRYUNHQO-UHFFFAOYSA-N 0.000 description 1
• DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
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• AJANBDUTHUKJSW-UHFFFAOYSA-N tricyclohexyloxy(hept-6-enyl)silane Chemical compound C1CCCCC1O[Si](OC1CCCCC1)(CCCCCC=C)OC1CCCCC1 AJANBDUTHUKJSW-UHFFFAOYSA-N 0.000 description 1
• KOHPCEUFMXPGGF-UHFFFAOYSA-N trihexoxy(oct-7-enyl)silane Chemical compound CCCCCCO[Si](OCCCCCC)(OCCCCCC)CCCCCCC=C KOHPCEUFMXPGGF-UHFFFAOYSA-N 0.000 description 1
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• MZGUIAFRJWSYJJ-UHFFFAOYSA-M trimethylstannanylium;bromide Chemical compound C[Sn](C)(C)Br MZGUIAFRJWSYJJ-UHFFFAOYSA-M 0.000 description 1
• NRZJSHMHHFWKBV-UHFFFAOYSA-N undec-10-enenitrile Chemical compound C=CCCCCCCCCC#N NRZJSHMHHFWKBV-UHFFFAOYSA-N 0.000 description 1
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