MD4247C1 - Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. - Google Patents
Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr.Info
- Publication number
- MD4247C1 MD4247C1 MDA20120126A MD20120126A MD4247C1 MD 4247 C1 MD4247 C1 MD 4247C1 MD A20120126 A MDA20120126 A MD A20120126A MD 20120126 A MD20120126 A MD 20120126A MD 4247 C1 MD4247 C1 MD 4247C1
- Authority
- MD
- Moldova
- Prior art keywords
- cis
- alcohol
- synthesis
- sex pheromone
- dodecenyl acetate
- Prior art date
Links
- 230000015572 biosynthetic process Effects 0.000 title claims abstract description 26
- 238000003786 synthesis reaction Methods 0.000 title claims abstract description 26
- SUCYDSJQVVGOIW-WAYWQWQTSA-N 8Z-Dodecenyl acetate Chemical compound CCC\C=C/CCCCCCCOC(C)=O SUCYDSJQVVGOIW-WAYWQWQTSA-N 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims abstract description 8
- 230000008569 process Effects 0.000 title claims abstract description 7
- 239000000877 Sex Attractant Substances 0.000 title abstract description 9
- 241000923682 Grapholita funebrana Species 0.000 title abstract 3
- 241000659076 Grapholitha Species 0.000 title description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 45
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims abstract description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims abstract description 10
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims abstract description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 claims abstract description 5
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 claims abstract description 4
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012346 acetyl chloride Substances 0.000 claims abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract description 3
- 238000010511 deprotection reaction Methods 0.000 claims abstract description 3
- 125000003186 propargylic group Chemical group 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 230000003993 interaction Effects 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 1
- 230000009466 transformation Effects 0.000 claims 1
- -1 acetylene alcohol Chemical compound 0.000 abstract description 5
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract description 5
- 230000004071 biological effect Effects 0.000 abstract description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 abstract description 3
- 230000009467 reduction Effects 0.000 abstract description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 abstract description 2
- 150000002894 organic compounds Chemical class 0.000 abstract description 2
- 235000021018 plums Nutrition 0.000 abstract description 2
- 125000001412 tetrahydropyranyl group Chemical group 0.000 abstract description 2
- 230000021736 acetylation Effects 0.000 abstract 1
- 238000006640 acetylation reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000004215 Carbon black (E152) Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000003016 pheromone Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YEQONIQGGSENJQ-PLNGDYQASA-N (z)-dodec-8-en-1-ol Chemical compound CCC\C=C/CCCCCCCO YEQONIQGGSENJQ-PLNGDYQASA-N 0.000 description 2
- PDKMGJGWXQNQGL-UHFFFAOYSA-N 1-chloro-1-iodohexane Chemical compound CCCCCC(Cl)I PDKMGJGWXQNQGL-UHFFFAOYSA-N 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- 230000001568 sexual effect Effects 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- VBYPENUQSSBEKQ-UHFFFAOYSA-N 1-bromohexane hydrobromide Chemical compound Br.BrCCCCCC VBYPENUQSSBEKQ-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000659001 Grapholitha molesta Species 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- MQRWBMAEBQOWAF-UHFFFAOYSA-N acetic acid;nickel Chemical compound [Ni].CC(O)=O.CC(O)=O MQRWBMAEBQOWAF-UHFFFAOYSA-N 0.000 description 1
- 230000000397 acetylating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007333 cyanation reaction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 1
- 229940078494 nickel acetate Drugs 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 231100000925 very toxic Toxicity 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20120126A MD4247C1 (ro) | 2012-10-19 | 2012-10-19 | Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20120126A MD4247C1 (ro) | 2012-10-19 | 2012-10-19 | Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4247B1 MD4247B1 (en) | 2013-08-31 |
| MD4247C1 true MD4247C1 (ro) | 2014-03-31 |
Family
ID=49117532
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20120126A MD4247C1 (ro) | 2012-10-19 | 2012-10-19 | Procedeu de sinteză a cis-8-dodecenilacetatului - feromon sexual al viermelui prunelor Grapholitha funebrana Tr. |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4247C1 (mo) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109609609B (zh) * | 2019-01-25 | 2022-04-19 | 河北出入境检验检疫局检验检疫技术中心 | 一种李小食心虫的实时荧光pcr检测方法 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3906035A (en) * | 1973-01-30 | 1975-09-16 | Commw Scient Ind Res Org | Process for the preparation of cis-8-dodecen-1-ol acetate |
| GB1504077A (en) * | 1975-07-08 | 1978-03-15 | Procida | Method for controlling cryptophlebia leucotreta using dodecenyl acetate |
| US4877891A (en) * | 1987-08-08 | 1989-10-31 | Basf Aktiengesellschaft | 1,1-dialkoxy- or 1,1-(alpha, omega-methylenedioxy)-non-2-yn-9-01 and their OH-protected derivatives |
| JPH08231304A (ja) * | 1995-02-24 | 1996-09-10 | Norin Suisansyo Sanshi Konchu Nogyo Gijutsu Kenkyusho | キボシカミキリの性刺激剤 |
| US6838576B1 (en) * | 2003-10-23 | 2005-01-04 | 3M Innovative Properties Company | Process for preparing functional group-containing olefinic compounds |
-
2012
- 2012-10-19 MD MDA20120126A patent/MD4247C1/ro not_active IP Right Cessation
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3906035A (en) * | 1973-01-30 | 1975-09-16 | Commw Scient Ind Res Org | Process for the preparation of cis-8-dodecen-1-ol acetate |
| GB1504077A (en) * | 1975-07-08 | 1978-03-15 | Procida | Method for controlling cryptophlebia leucotreta using dodecenyl acetate |
| US4877891A (en) * | 1987-08-08 | 1989-10-31 | Basf Aktiengesellschaft | 1,1-dialkoxy- or 1,1-(alpha, omega-methylenedioxy)-non-2-yn-9-01 and their OH-protected derivatives |
| JPH08231304A (ja) * | 1995-02-24 | 1996-09-10 | Norin Suisansyo Sanshi Konchu Nogyo Gijutsu Kenkyusho | キボシカミキリの性刺激剤 |
| US6838576B1 (en) * | 2003-10-23 | 2005-01-04 | 3M Innovative Properties Company | Process for preparing functional group-containing olefinic compounds |
Non-Patent Citations (4)
| Title |
|---|
| Holan G. and O,Keefe D.F. An improved synthesis of insect sex attractant: cis-8-dodecen-1-ol acetate. Tetrahedron Letters, No 9, pp. 673-674, 1973 * |
| Kenji Mori and Takuya Tashiro. Useful reactions in Modern Pheromone Synthesis. Current Organic Synthesis, 2004, 1, 11-29, Regăsit în Internet la 2013.06.24, url: http://benthamscience.com/cos/sample/cos1-1/Mori.pdf * |
| Kenji Mori. The Synthesis of Insect Pheromones, in The Total Synthesis of Natural Products, Vol. 4, 1981. Edited by John ApSimer vezi pag. 6, 9-10, 25-26 * |
| Одиноков В.Н., Ишмуратов Г.Ю., Балезина Г.Г., Толстиков Г.А. Феромоны насекомых и их аналоги. ХIII. Синтез (Е)- и (Z)-8-додеценилацетатов - компонентов половых феромонов Grapholitha funebrana и Grapholitha molesta. Химия природных соединений, № 3, с. 398-400, 1985 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4247B1 (en) | 2013-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |