IL269164B2 - A new preparation of isomers of 7,9-dodecadienyl-1-acetate and a process for its production - Google Patents
A new preparation of isomers of 7,9-dodecadienyl-1-acetate and a process for its productionInfo
- Publication number
- IL269164B2 IL269164B2 IL269164A IL26916419A IL269164B2 IL 269164 B2 IL269164 B2 IL 269164B2 IL 269164 A IL269164 A IL 269164A IL 26916419 A IL26916419 A IL 26916419A IL 269164 B2 IL269164 B2 IL 269164B2
- Authority
- IL
- Israel
- Prior art keywords
- isomer
- mixture
- isomers
- formula
- alkyl group
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 67
- 238000000034 method Methods 0.000 title claims description 43
- 230000008569 process Effects 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 enol phosphate isomers Chemical class 0.000 claims description 36
- 150000001875 compounds Chemical class 0.000 claims description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 229910019142 PO4 Inorganic materials 0.000 claims description 14
- 239000010452 phosphate Substances 0.000 claims description 14
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 12
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 10
- 230000010933 acylation Effects 0.000 claims description 7
- 238000005917 acylation reaction Methods 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 7
- 150000002148 esters Chemical class 0.000 claims description 7
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 7
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- NNDAMUJSVJJJJY-UHFFFAOYSA-N (5-ethyl-5-methylhepta-1,3-dienyl) dihydrogen phosphate Chemical compound CCC(C)(CC)C=CC=COP(O)(O)=O NNDAMUJSVJJJJY-UHFFFAOYSA-N 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 5
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- 230000008030 elimination Effects 0.000 claims description 3
- 238000003379 elimination reaction Methods 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- ITLSMVWXXNJUQO-FLYFVYFHSA-N (E)-hex-2-enal Chemical compound CCC\C=C\C=O.CCC\C=C\C=O ITLSMVWXXNJUQO-FLYFVYFHSA-N 0.000 claims description 2
- 239000001179 (E)-hex-2-enal Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- MBDOYVRWFFCFHM-UHFFFAOYSA-N trans-2-hexenal Natural products CCCC=CC=O MBDOYVRWFFCFHM-UHFFFAOYSA-N 0.000 claims description 2
- 238000003786 synthesis reaction Methods 0.000 description 22
- 239000003016 pheromone Substances 0.000 description 20
- 230000015572 biosynthetic process Effects 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 10
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 9
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 9
- 239000004202 carbamide Substances 0.000 description 9
- LLRZUAWETKPZJO-UHFFFAOYSA-N dodeca-7,9-dienyl acetate Chemical compound CCC=CC=CCCCCCCOC(C)=O LLRZUAWETKPZJO-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 8
- 238000000746 purification Methods 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 150000001993 dienes Chemical group 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000037361 pathway Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000005698 Diels-Alder reaction Methods 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 241000607479 Yersinia pestis Species 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007818 Grignard reagent Substances 0.000 description 3
- 241000238631 Hexapoda Species 0.000 description 3
- 241001261104 Lobesia botrana Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 241000305201 Phalaenoides glycinae Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LLRZUAWETKPZJO-DEQVHDEQSA-N [(7z,9e)-dodeca-7,9-dienyl] acetate Chemical compound CC\C=C\C=C/CCCCCCOC(C)=O LLRZUAWETKPZJO-DEQVHDEQSA-N 0.000 description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005859 coupling reaction Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- 230000001939 inductive effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000011282 treatment Methods 0.000 description 3
- JZQKTMZYLHNFPL-NMMTYZSQSA-N (e,e)-2,4-decadienal Chemical compound CCCCC\C=C/C=C/C=O JZQKTMZYLHNFPL-NMMTYZSQSA-N 0.000 description 2
- UQRONKZLYKUEMO-UHFFFAOYSA-N 4-methyl-1-(2,4,6-trimethylphenyl)pent-4-en-2-one Chemical group CC(=C)CC(=O)Cc1c(C)cc(C)cc1C UQRONKZLYKUEMO-UHFFFAOYSA-N 0.000 description 2
- SSGXHMNJZLXQIW-DNVGVPOPSA-N 7E,9Z-dodecadien-1-ol Chemical compound CC\C=C/C=C/CCCCCCO SSGXHMNJZLXQIW-DNVGVPOPSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 239000000877 Sex Attractant Substances 0.000 description 2
- 235000014787 Vitis vinifera Nutrition 0.000 description 2
- 240000006365 Vitis vinifera Species 0.000 description 2
- 238000007239 Wittig reaction Methods 0.000 description 2
- RFEQLTBBKNKGGJ-RZSVFLSASA-N [(9z,11z)-tetradeca-9,11-dienyl] acetate Chemical compound CC\C=C/C=C\CCCCCCCCOC(C)=O RFEQLTBBKNKGGJ-RZSVFLSASA-N 0.000 description 2
- 230000021736 acetylation Effects 0.000 description 2
- 238000006640 acetylation reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000003849 aromatic solvent Substances 0.000 description 2
- 230000008901 benefit Effects 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- TUKWYTVHOYMJPV-UHFFFAOYSA-N diethyl hexa-1,3-dienyl phosphate Chemical compound P(=O)(OCC)(OCC)OC=CC=CCC TUKWYTVHOYMJPV-UHFFFAOYSA-N 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 150000002681 magnesium compounds Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000003828 vacuum filtration Methods 0.000 description 2
- OSFASEAZCNYZBW-SCFJQAPRSA-N (10E,12Z)-Hexadeca-10,12-dienal Chemical compound CCC\C=C/C=C/CCCCCCCCC=O OSFASEAZCNYZBW-SCFJQAPRSA-N 0.000 description 1
- OSFASEAZCNYZBW-DEQVHDEQSA-N (10Z,12E)-hexadecadienal Chemical compound CCC\C=C\C=C/CCCCCCCCC=O OSFASEAZCNYZBW-DEQVHDEQSA-N 0.000 description 1
- POHNQQRJOMLPNT-SCFJQAPRSA-N (10e,12z)-hexadeca-10,12-dienoic acid Chemical compound CCC\C=C/C=C/CCCCCCCCC(O)=O POHNQQRJOMLPNT-SCFJQAPRSA-N 0.000 description 1
- ZTJGMVSDMQAJPE-DNVGVPOPSA-N (11e,13z)-hexadeca-11,13-dienal Chemical compound CC\C=C/C=C/CCCCCCCCCC=O ZTJGMVSDMQAJPE-DNVGVPOPSA-N 0.000 description 1
- MBDOYVRWFFCFHM-SNAWJCMRSA-N (2E)-hexenal Chemical compound CCC\C=C\C=O MBDOYVRWFFCFHM-SNAWJCMRSA-N 0.000 description 1
- JZQKTMZYLHNFPL-ANYPYVPJSA-N (2E, 4Z)-form-2, 4-Decadienal Natural products CCCCCC=C\C=C\C=O JZQKTMZYLHNFPL-ANYPYVPJSA-N 0.000 description 1
- GIBJEWOSWWYJSK-CZVXUDSPSA-N (2z,4e)-3,7,11-trimethyldodeca-2,4,10-triene Chemical compound C\C=C(\C)/C=C/CC(C)CCC=C(C)C GIBJEWOSWWYJSK-CZVXUDSPSA-N 0.000 description 1
- QUFVBBANWSSNQF-CZVXUDSPSA-N (2z,4e)-3,7,11-trimethyldodeca-2,4-diene Chemical compound C\C=C(\C)/C=C/CC(C)CCCC(C)C QUFVBBANWSSNQF-CZVXUDSPSA-N 0.000 description 1
- YRUMHTHCEZRHTN-XAZJVICWSA-N (3E,5Z)-tetradecadienoic acid Chemical compound CCCCCCCC\C=C/C=C/CC(O)=O YRUMHTHCEZRHTN-XAZJVICWSA-N 0.000 description 1
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- LDQDYNHCLZNOFB-UHFFFAOYSA-N (5Z,7E)-5,7-Dodecadienal Natural products CCCCC=CC=CCCCC=O LDQDYNHCLZNOFB-UHFFFAOYSA-N 0.000 description 1
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- LDQDYNHCLZNOFB-ISTTXYCBSA-N (5z,7z)-dodeca-5,7-dienal Chemical compound CCCC\C=C/C=C\CCCC=O LDQDYNHCLZNOFB-ISTTXYCBSA-N 0.000 description 1
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- PSXWLIOQHPZSOF-QRLRYFCNSA-N (8Z,10Z)-heptadeca-8,10-dien-1-ol Chemical compound C(CCCCCC\C=C/C=C\CCCCCC)O PSXWLIOQHPZSOF-QRLRYFCNSA-N 0.000 description 1
- CSWBSLXBXRFNST-AWYLAFAOSA-N (8e,10z)-dodeca-8,10-dien-1-ol Chemical compound C\C=C/C=C/CCCCCCCO CSWBSLXBXRFNST-AWYLAFAOSA-N 0.000 description 1
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- ZZZXZQQRTBBNHT-UHFFFAOYSA-N 1-chloropentan-1-ol Chemical class CCCCC(O)Cl ZZZXZQQRTBBNHT-UHFFFAOYSA-N 0.000 description 1
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- ZNOVTXRBGFNYRX-UHFFFAOYSA-N 2-[[4-[(2-amino-5-methyl-4-oxo-1,6,7,8-tetrahydropteridin-6-yl)methylamino]benzoyl]amino]pentanedioic acid Chemical compound C1NC=2NC(N)=NC(=O)C=2N(C)C1CNC1=CC=C(C(=O)NC(CCC(O)=O)C(O)=O)C=C1 ZNOVTXRBGFNYRX-UHFFFAOYSA-N 0.000 description 1
- ZKUWHODMAHRIFM-QNRZBPGKSA-N 3E,5Z-Dodecadienyl acetate Chemical compound CCCCCC\C=C/C=C/CCOC(C)=O ZKUWHODMAHRIFM-QNRZBPGKSA-N 0.000 description 1
- JNTPTNNCGDAGEJ-UHFFFAOYSA-N 6-chlorohexan-1-ol Chemical compound OCCCCCCCl JNTPTNNCGDAGEJ-UHFFFAOYSA-N 0.000 description 1
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- ZKCFLTTYWFSLDK-ICWBMWKASA-N 9Z,11E-Tetradecadien-1-ol Chemical compound CC\C=C\C=C/CCCCCCCCO ZKCFLTTYWFSLDK-ICWBMWKASA-N 0.000 description 1
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- 238000006261 Adler reaction Methods 0.000 description 1
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- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 241001261102 Lobesia Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- 101100074998 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-2 gene Proteins 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- CMCBHGAXGCXMIP-IGTJQSIKSA-N [(10e,12z)-hexadeca-10,12-dienyl] acetate Chemical compound CCC\C=C/C=C/CCCCCCCCCOC(C)=O CMCBHGAXGCXMIP-IGTJQSIKSA-N 0.000 description 1
- BJAQMNWCYXNBJY-DNVGVPOPSA-N [(10e,12z)-tetradeca-10,12-dienyl] acetate Chemical compound C\C=C/C=C/CCCCCCCCCOC(C)=O BJAQMNWCYXNBJY-DNVGVPOPSA-N 0.000 description 1
- CMCBHGAXGCXMIP-MDAAKZFYSA-N [(10z,12e)-hexadeca-10,12-dienyl] acetate Chemical compound CCC\C=C\C=C/CCCCCCCCCOC(C)=O CMCBHGAXGCXMIP-MDAAKZFYSA-N 0.000 description 1
- BJAQMNWCYXNBJY-ICWBMWKASA-N [(10z,12e)-tetradeca-10,12-dienyl] acetate Chemical compound C\C=C\C=C/CCCCCCCCCOC(C)=O BJAQMNWCYXNBJY-ICWBMWKASA-N 0.000 description 1
- BJAQMNWCYXNBJY-OUPQRBNQSA-N [(10z,12z)-tetradeca-10,12-dienyl] acetate Chemical compound C\C=C/C=C\CCCCCCCCCOC(C)=O BJAQMNWCYXNBJY-OUPQRBNQSA-N 0.000 description 1
- JDEZPVDDXSKIMP-SCFJQAPRSA-N [(11e,13z)-hexadeca-11,13-dienyl] acetate Chemical compound CC\C=C/C=C/CCCCCCCCCCOC(C)=O JDEZPVDDXSKIMP-SCFJQAPRSA-N 0.000 description 1
- TXBXMQGKTRAYAK-SCFJQAPRSA-N [(2e,4z)-hepta-2,4-dienyl] acetate Chemical compound CC\C=C/C=C/COC(C)=O TXBXMQGKTRAYAK-SCFJQAPRSA-N 0.000 description 1
- XXIIMWWMOJXDLK-JPYSRSMKSA-N [(3e,5z)-tetradeca-3,5-dienyl] acetate Chemical compound CCCCCCCC\C=C/C=C/CCOC(C)=O XXIIMWWMOJXDLK-JPYSRSMKSA-N 0.000 description 1
- BBALEUFMAFGKSL-MUIOLIGRSA-N [(3z,5e)-deca-3,5-dienyl] acetate Chemical compound CCCC\C=C\C=C/CCOC(C)=O BBALEUFMAFGKSL-MUIOLIGRSA-N 0.000 description 1
- ZKUWHODMAHRIFM-OCBXPSTGSA-N [(3z,5e)-dodeca-3,5-dienyl] acetate Chemical compound CCCCCC\C=C\C=C/CCOC(C)=O ZKUWHODMAHRIFM-OCBXPSTGSA-N 0.000 description 1
- XXIIMWWMOJXDLK-MRBUWEIXSA-N [(3z,5e)-tetradeca-3,5-dienyl] acetate Chemical compound CCCCCCCC\C=C\C=C/CCOC(C)=O XXIIMWWMOJXDLK-MRBUWEIXSA-N 0.000 description 1
- LILNZTGQAGPWKK-NMMTYZSQSA-N [(5e,7z)-dodeca-5,7-dienyl] acetate Chemical compound CCCC\C=C/C=C/CCCCOC(C)=O LILNZTGQAGPWKK-NMMTYZSQSA-N 0.000 description 1
- LILNZTGQAGPWKK-MUIOLIGRSA-N [(5z,7e)-dodeca-5,7-dienyl] acetate Chemical compound CCCC\C=C\C=C/CCCCOC(C)=O LILNZTGQAGPWKK-MUIOLIGRSA-N 0.000 description 1
- FDPOUOBXISIHOH-GOJKSUSPSA-N [(5z,7e)-dodeca-5,7-dienyl] propanoate Chemical compound CCCC\C=C\C=C/CCCCOC(=O)CC FDPOUOBXISIHOH-GOJKSUSPSA-N 0.000 description 1
- LILNZTGQAGPWKK-JPDBVBESSA-N [(5z,7z)-dodeca-5,7-dienyl] acetate Chemical compound CCCC\C=C/C=C\CCCCOC(C)=O LILNZTGQAGPWKK-JPDBVBESSA-N 0.000 description 1
- LLRZUAWETKPZJO-RZSVFLSASA-N [(7z,9z)-dodeca-7,9-dienyl] acetate Chemical compound CC\C=C/C=C\CCCCCCOC(C)=O LLRZUAWETKPZJO-RZSVFLSASA-N 0.000 description 1
- NTKDSWPSEFZZOZ-DNVGVPOPSA-N [(8e,10z)-dodeca-8,10-dienyl] acetate Chemical compound C\C=C/C=C/CCCCCCCOC(C)=O NTKDSWPSEFZZOZ-DNVGVPOPSA-N 0.000 description 1
- IXHOWPHRHRFHPB-NMMTYZSQSA-N [(8e,10z)-pentadeca-8,10-dienyl] acetate Chemical compound CCCC\C=C/C=C/CCCCCCCOC(C)=O IXHOWPHRHRFHPB-NMMTYZSQSA-N 0.000 description 1
- NTKDSWPSEFZZOZ-ICWBMWKASA-N [(8z,10e)-dodeca-8,10-dienyl] acetate Chemical compound C\C=C\C=C/CCCCCCCOC(C)=O NTKDSWPSEFZZOZ-ICWBMWKASA-N 0.000 description 1
- IXHOWPHRHRFHPB-MUIOLIGRSA-N [(8z,10e)-pentadeca-8,10-dienyl] acetate Chemical compound CCCC\C=C\C=C/CCCCCCCOC(C)=O IXHOWPHRHRFHPB-MUIOLIGRSA-N 0.000 description 1
- UOGXIKWNCIJUKX-MDAAKZFYSA-N [(8z,10e)-tetradeca-8,10-dienyl] acetate Chemical compound CCC\C=C\C=C/CCCCCCCOC(C)=O UOGXIKWNCIJUKX-MDAAKZFYSA-N 0.000 description 1
- NTKDSWPSEFZZOZ-OUPQRBNQSA-N [(8z,10z)-dodeca-8,10-dienyl] acetate Chemical compound C\C=C/C=C\CCCCCCCOC(C)=O NTKDSWPSEFZZOZ-OUPQRBNQSA-N 0.000 description 1
- IXHOWPHRHRFHPB-JPDBVBESSA-N [(8z,10z)-pentadeca-8,10-dienyl] acetate Chemical compound CCCC\C=C/C=C\CCCCCCCOC(C)=O IXHOWPHRHRFHPB-JPDBVBESSA-N 0.000 description 1
- PVWRDCRRLIFQRN-NMMTYZSQSA-N [(9e,11z)-hexadeca-9,11-dienyl] acetate Chemical compound CCCC\C=C/C=C/CCCCCCCCOC(C)=O PVWRDCRRLIFQRN-NMMTYZSQSA-N 0.000 description 1
- RFEQLTBBKNKGGJ-SCFJQAPRSA-N [(9e,11z)-tetradeca-9,11-dienyl] acetate Chemical compound CC\C=C/C=C/CCCCCCCCOC(C)=O RFEQLTBBKNKGGJ-SCFJQAPRSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- CIVIWCVVOFNUST-SCFJQAPRSA-N bombykol Chemical compound CCC\C=C/C=C/CCCCCCCCCO CIVIWCVVOFNUST-SCFJQAPRSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical class CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 150000001879 copper Chemical class 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical class C1(=CCCCC1)* 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- HXJFQNUWPUICNY-UHFFFAOYSA-N disiamylborane Chemical compound CC(C)C(C)BC(C)C(C)C HXJFQNUWPUICNY-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- OPCRGEVPIBLWAY-QNRZBPGKSA-N ethyl (2E,4Z)-deca-2,4-dienoate Chemical compound CCCCC\C=C/C=C/C(=O)OCC OPCRGEVPIBLWAY-QNRZBPGKSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003163 gonadal steroid hormone Substances 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
- UBSXYTUCWIMCTG-UHFFFAOYSA-N hepta-1,3-dien-3-yl 2-methylpropanoate Chemical compound C(C(C)C)(=O)OC(C=C)=CCCC UBSXYTUCWIMCTG-UHFFFAOYSA-N 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- QUXHCILOWRXCEO-UHFFFAOYSA-M magnesium;butane;chloride Chemical compound [Mg+2].[Cl-].CCC[CH2-] QUXHCILOWRXCEO-UHFFFAOYSA-M 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- SFHSEXGIVSBRRK-UQGDGPGGSA-N methyl (2e,4z)-deca-2,4-dienoate Chemical compound CCCCC\C=C/C=C/C(=O)OC SFHSEXGIVSBRRK-UQGDGPGGSA-N 0.000 description 1
- 239000002480 mineral oil Substances 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
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- WKNMSTAGPNHPGW-UHFFFAOYSA-N pent-1-en-3-yl 2-methylpropanoate Chemical compound CCC(C=C)OC(=O)C(C)C WKNMSTAGPNHPGW-UHFFFAOYSA-N 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- 230000001131 transforming effect Effects 0.000 description 1
- MSXNDXIAUQJHNS-UHFFFAOYSA-N triphenyl(propyl)phosphanium Chemical compound C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 MSXNDXIAUQJHNS-UHFFFAOYSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- 239000012808 vapor phase Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/141—Esters of phosphorous acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic alcohols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/68—Preparation of metal alcoholates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/09—Geometrical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1751979A FR3063729B1 (fr) | 2017-03-10 | 2017-03-10 | Nouvelle composition d'isomeres du 7,9-dodecadienyl-1-acetate et son procede de fabrication |
| PCT/EP2018/055956 WO2018162739A1 (fr) | 2017-03-10 | 2018-03-09 | Nouvelle composition d'isomeres du 7,9-dodécadiényl-1-acétate et son procede de fabrication |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| IL269164A IL269164A (en) | 2019-11-28 |
| IL269164B IL269164B (en) | 2022-12-01 |
| IL269164B2 true IL269164B2 (en) | 2023-04-01 |
Family
ID=59070800
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL269164A IL269164B2 (en) | 2017-03-10 | 2018-03-09 | A new preparation of isomers of 7,9-dodecadienyl-1-acetate and a process for its production |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US11649257B2 (https=) |
| EP (1) | EP3592753B1 (https=) |
| JP (1) | JP7145166B2 (https=) |
| CN (1) | CN110891957B (https=) |
| AU (1) | AU2018231608B2 (https=) |
| CA (1) | CA3055861A1 (https=) |
| EA (1) | EA201992111A1 (https=) |
| ES (1) | ES2909843T3 (https=) |
| FR (1) | FR3063729B1 (https=) |
| IL (1) | IL269164B2 (https=) |
| MX (1) | MX2019010753A (https=) |
| WO (1) | WO2018162739A1 (https=) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3164211A1 (fr) | 2024-07-02 | 2026-01-09 | Melchior Material And Life Science France | Procédé de préparation en flux continu d’un mélange d’isomères de l’hexa-1,3-dién-1-yl-diéthylphosphate |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3394201A (en) | 1966-11-25 | 1968-07-23 | Dow Chemical Co | Separation of high purity 4-methyl-1, 3-pentadiene |
| US3845108A (en) | 1973-08-31 | 1974-10-29 | W Roelofs | Trans-7-cis-9-dodecadien-1-yl acetate |
| US4014946A (en) | 1974-11-25 | 1977-03-29 | Zoecon Corporation | Synthesis of 1-bromonon-4-en-6-yne |
| US3954818A (en) | 1974-11-25 | 1976-05-04 | Zoecon Corporation | Synthesis of non-4-en-6-ynoic acid ester |
| FR2341546A1 (fr) | 1976-02-20 | 1977-09-16 | Anvar | Nouveau procede de synthese stereoselective de composes dieniques e, z possedant une chaine de 12 a 16 atomes de carbone ainsi que de leurs precurseurs immediats les enynes conjugues e |
| JPS62223136A (ja) | 1986-03-19 | 1987-10-01 | Shin Etsu Chem Co Ltd | １―ハロ―（ｅ，ｚ）―７，９―アルカジエン化合物 |
| DE3817399A1 (de) * | 1988-05-21 | 1989-11-30 | Basf Ag | Verfahren zur herstellung von e7/z9-alkadien-1-olen und deren an der hydroxylgruppe geschuetzten derivaten |
| JPH07116075B2 (ja) | 1988-06-06 | 1995-12-13 | 信越化学工業株式会社 | 不飽和アルコール化合物の製造方法 |
| JP3619277B2 (ja) * | 1995-02-10 | 2005-02-09 | 株式会社日清製粉グループ本社 | ジヒドロポリプレニルモノホスフェートの製造方法及びその中間体化合物 |
| US7932410B2 (en) | 2008-10-31 | 2011-04-26 | Bedoukian Research, Inc. | Production of pheromones and fragrances from substituted and unsubstituted 1-alken-3yl alkylates |
| FR3023291B1 (fr) * | 2014-07-02 | 2016-07-22 | Melchior Material & Life Science France | Nouveau procede de fabrication du (e,z)-7,9 dodecandienyl-1-acetate |
-
2017
- 2017-03-10 FR FR1751979A patent/FR3063729B1/fr active Active
-
2018
- 2018-03-09 JP JP2019549421A patent/JP7145166B2/ja active Active
- 2018-03-09 AU AU2018231608A patent/AU2018231608B2/en not_active Ceased
- 2018-03-09 MX MX2019010753A patent/MX2019010753A/es unknown
- 2018-03-09 EA EA201992111A patent/EA201992111A1/ru unknown
- 2018-03-09 ES ES18708445T patent/ES2909843T3/es active Active
- 2018-03-09 IL IL269164A patent/IL269164B2/en unknown
- 2018-03-09 US US16/492,256 patent/US11649257B2/en active Active
- 2018-03-09 CN CN201880027867.2A patent/CN110891957B/zh active Active
- 2018-03-09 EP EP18708445.4A patent/EP3592753B1/fr active Active
- 2018-03-09 CA CA3055861A patent/CA3055861A1/fr active Pending
- 2018-03-09 WO PCT/EP2018/055956 patent/WO2018162739A1/fr not_active Ceased
-
2023
- 2023-04-03 US US18/130,133 patent/US20230234977A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN110891957B (zh) | 2022-12-23 |
| JP7145166B2 (ja) | 2022-09-30 |
| IL269164A (en) | 2019-11-28 |
| EP3592753A1 (fr) | 2020-01-15 |
| US20200354387A1 (en) | 2020-11-12 |
| AU2018231608B2 (en) | 2021-05-20 |
| WO2018162739A1 (fr) | 2018-09-13 |
| EA201992111A1 (ru) | 2020-02-20 |
| US20230234977A1 (en) | 2023-07-27 |
| CN110891957A (zh) | 2020-03-17 |
| JP2020510685A (ja) | 2020-04-09 |
| US11649257B2 (en) | 2023-05-16 |
| EP3592753B1 (fr) | 2022-02-16 |
| MX2019010753A (es) | 2020-01-20 |
| FR3063729A1 (fr) | 2018-09-14 |
| AU2018231608A1 (en) | 2019-10-03 |
| ES2909843T3 (es) | 2022-05-10 |
| FR3063729B1 (fr) | 2019-06-07 |
| CA3055861A1 (fr) | 2018-09-13 |
| IL269164B (en) | 2022-12-01 |
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