SU1209027A3 - Способ получени производных бицикло (2,2,1) гептана в виде рацемата или оптически активного антипода - Google Patents
Способ получени производных бицикло (2,2,1) гептана в виде рацемата или оптически активного антипода Download PDFInfo
- Publication number
- SU1209027A3 SU1209027A3 SU813369302A SU3369302A SU1209027A3 SU 1209027 A3 SU1209027 A3 SU 1209027A3 SU 813369302 A SU813369302 A SU 813369302A SU 3369302 A SU3369302 A SU 3369302A SU 1209027 A3 SU1209027 A3 SU 1209027A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- group
- compound
- optically active
- heptane
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 11
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 29
- -1 phenyl- Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000003544 oxime group Chemical group 0.000 claims abstract 6
- 239000003795 chemical substances by application Substances 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Substances 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 238000009835 boiling Methods 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 6
- 239000008096 xylene Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 claims 1
- 150000008046 alkali metal hydrides Chemical class 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000007530 organic bases Chemical class 0.000 claims 1
- 239000011593 sulfur Chemical group 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 230000008635 plant growth Effects 0.000 abstract description 5
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000002344 aminooxy group Chemical group [H]N([H])O[*] 0.000 abstract 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 abstract 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 abstract 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 230000035784 germination Effects 0.000 description 23
- 241000196324 Embryophyta Species 0.000 description 13
- 238000011282 treatment Methods 0.000 description 13
- 240000008042 Zea mays Species 0.000 description 11
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 11
- 238000005507 spraying Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 9
- 235000005822 corn Nutrition 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 240000004713 Pisum sativum Species 0.000 description 7
- 235000010582 Pisum sativum Nutrition 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 241000227653 Lycopersicon Species 0.000 description 5
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 5
- 244000020551 Helianthus annuus Species 0.000 description 4
- 235000003222 Helianthus annuus Nutrition 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000012545 processing Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000005292 vacuum distillation Methods 0.000 description 4
- 235000013339 cereals Nutrition 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- UTPHVTOEOCZQJU-UHFFFAOYSA-N 4-methylbicyclo[2.2.1]heptane Chemical compound C1CC2CCC1(C)C2 UTPHVTOEOCZQJU-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 2
- 229940073608 benzyl chloride Drugs 0.000 description 2
- 239000012230 colorless oil Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000009973 maize Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001105 regulatory effect Effects 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- PQNFIEMAKATKQF-UHFFFAOYSA-N 1,7,7-trimethyl-N-phenylmethoxybicyclo[2.2.1]heptan-2-imine Chemical compound CC1(C)C(C2)CCC1(C)C2=NOCC1=CC=CC=C1 PQNFIEMAKATKQF-UHFFFAOYSA-N 0.000 description 1
- PBLNBZIONSLZBU-UHFFFAOYSA-N 1-bromododecane Chemical compound CCCCCCCCCCCCBr PBLNBZIONSLZBU-UHFFFAOYSA-N 0.000 description 1
- CYNYIHKIEHGYOZ-UHFFFAOYSA-N 1-bromopropane Chemical compound CCCBr CYNYIHKIEHGYOZ-UHFFFAOYSA-N 0.000 description 1
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 240000002791 Brassica napus Species 0.000 description 1
- 235000004977 Brassica sinapistrum Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 235000007340 Hordeum vulgare Nutrition 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 description 1
- KPFBUSLHFFWMAI-HYRPPVSQSA-N [(8r,9s,10r,13s,14s,17r)-17-acetyl-6-formyl-3-methoxy-10,13-dimethyl-1,2,7,8,9,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-17-yl] acetate Chemical compound C1C[C@@H]2[C@](CCC(OC)=C3)(C)C3=C(C=O)C[C@H]2[C@@H]2CC[C@](OC(C)=O)(C(C)=O)[C@]21C KPFBUSLHFFWMAI-HYRPPVSQSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- BHELZAPQIKSEDF-UHFFFAOYSA-N allyl bromide Chemical compound BrCC=C BHELZAPQIKSEDF-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000001511 capsicum annuum Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000004531 microgranule Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 235000012015 potatoes Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
- A01N35/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen containing a carbon-to-nitrogen double bond
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU802774A HU184353B (en) | 1980-11-21 | 1980-11-21 | Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1209027A3 true SU1209027A3 (ru) | 1986-01-30 |
Family
ID=10961039
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU813369302A SU1209027A3 (ru) | 1980-11-21 | 1981-11-20 | Способ получени производных бицикло (2,2,1) гептана в виде рацемата или оптически активного антипода |
Country Status (26)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU184353B (en) * | 1980-11-21 | 1984-08-28 | Egyt Gyogyszervegyeszeti Gyar | Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives |
| US4735943A (en) * | 1984-06-29 | 1988-04-05 | Sanwa Kagaku Kenkyusho Co., Ltd. | Eburnamonine oxime derivatives, salts thereof, and pharmaceutical agents containing the same |
| AU783024B2 (en) * | 2000-05-26 | 2005-09-15 | Ajinomoto Co., Inc. | Feed for livestock |
| JP6287499B2 (ja) * | 2014-04-02 | 2018-03-07 | 住友化学株式会社 | 重合性モノマー、樹脂、レジスト組成物及びレジストパターンの製造方法 |
| US20220162390A1 (en) * | 2019-03-20 | 2022-05-26 | Arizona Board Of Regents On Behalf Of The University Of Arizona | Chalcogenide hybrid organic/inorganic polymers and methods for producing and using the same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2031874B (en) * | 1978-08-22 | 1982-12-15 | Egyt Gyogyszervegyeszeti Gyar | Plant growth regulating and insecticidal compositions |
| HU181873B (en) * | 1978-08-22 | 1983-11-28 | Egyt Gyogyszervegyeszeti Gyar | Plant growth regulating and/or insecticide composition containing 2-/propagyl-oxy-imino/-1,7,7-trimethyl-byciclo/2.2.1/heptane further process for preparing the active suastance |
| HU184353B (en) * | 1980-11-21 | 1984-08-28 | Egyt Gyogyszervegyeszeti Gyar | Plant growth regulating composition containing bicyclo/2.2.1/ heptane derivative further process for preparing bicyclo/2.2.1/ heptane derivatives |
-
1980
- 1980-11-21 HU HU802774A patent/HU184353B/hu not_active IP Right Cessation
-
1981
- 1981-11-06 FI FI813498A patent/FI65529C/fi not_active IP Right Cessation
- 1981-11-16 BE BE1/10356A patent/BE891128A/fr not_active IP Right Cessation
- 1981-11-18 US US06/322,675 patent/US4425158A/en not_active Expired - Fee Related
- 1981-11-19 IL IL64319A patent/IL64319A/xx unknown
- 1981-11-19 ZA ZA818033A patent/ZA818033B/xx unknown
- 1981-11-19 GB GB8134890A patent/GB2087888B/en not_active Expired
- 1981-11-19 CH CH7430/81A patent/CH647756A5/de not_active IP Right Cessation
- 1981-11-19 AT AT0498381A patent/AT380233B/de not_active IP Right Cessation
- 1981-11-19 GR GR66572A patent/GR77308B/el unknown
- 1981-11-19 PL PL1981233896A patent/PL128561B1/pl unknown
- 1981-11-19 FR FR8121661A patent/FR2494687A1/fr active Granted
- 1981-11-19 NL NL8105235A patent/NL8105235A/nl not_active Application Discontinuation
- 1981-11-19 CS CS818509A patent/CS234037B2/cs unknown
- 1981-11-20 BG BG054236A patent/BG43523A3/xx unknown
- 1981-11-20 DD DD81235014A patent/DD202086A5/de unknown
- 1981-11-20 IT IT8125197A patent/IT1211134B/it active
- 1981-11-20 ES ES507350A patent/ES8207137A1/es not_active Expired
- 1981-11-20 SE SE8106926A patent/SE447377B/sv not_active IP Right Cessation
- 1981-11-20 DK DK516781A patent/DK516781A/da not_active Application Discontinuation
- 1981-11-20 DE DE19813146106 patent/DE3146106A1/de not_active Ceased
- 1981-11-20 SU SU813369302A patent/SU1209027A3/ru active
- 1981-11-20 ZW ZW282/81A patent/ZW28281A1/xx unknown
- 1981-11-20 IE IE2721/81A patent/IE51856B1/en unknown
- 1981-11-20 JP JP56186760A patent/JPS57116042A/ja active Pending
- 1981-11-21 EG EG677/81A patent/EG15682A/xx active
-
1983
- 1983-11-15 US US06/551,941 patent/US4511737A/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Патент FR № 2434148, кл. С 07 С 131/02, опублик. 21.03.80. * |
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