JPH04247052A - ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法 - Google Patents
ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法Info
- Publication number
- JPH04247052A JPH04247052A JP3029202A JP2920291A JPH04247052A JP H04247052 A JPH04247052 A JP H04247052A JP 3029202 A JP3029202 A JP 3029202A JP 2920291 A JP2920291 A JP 2920291A JP H04247052 A JPH04247052 A JP H04247052A
- Authority
- JP
- Japan
- Prior art keywords
- formula
- heptane
- compound shown
- dione
- bicyclo
- Prior art date
- 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
- ILPNRWUGFSPGAA-UHFFFAOYSA-N heptane-2,4-dione Chemical class CCCC(=O)CC(C)=O ILPNRWUGFSPGAA-UHFFFAOYSA-N 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000000126 substance Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 20
- 230000002363 herbicidal effect Effects 0.000 abstract description 5
- QQDXZWCZNAKRLO-CZGZLPJCSA-N ethyl (1r,6r)-5-methyl-2,4-dioxobicyclo[4.1.0]heptane-5-carboxylate Chemical compound O=C1CC(=O)C(C(=O)OCC)(C)[C@@H]2C[C@H]21 QQDXZWCZNAKRLO-CZGZLPJCSA-N 0.000 abstract description 4
- 239000004009 herbicide Substances 0.000 abstract description 3
- SVJULQUNOGJBNE-UHFFFAOYSA-N bicyclo[4.1.0]heptane-3,5-dione Chemical class O=C1CC(=O)CC2CC21 SVJULQUNOGJBNE-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 5
- 235000019341 magnesium sulphate Nutrition 0.000 description 5
- -1 2-substituted benzoyl-1,3-cyclohexanediones Chemical class 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 125000001559 cyclopropyl group Chemical class [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
- BWIKPHCVVVHICG-UHFFFAOYSA-N 5-chloropent-3-en-2-one Chemical compound CC(=O)C=CCCl BWIKPHCVVVHICG-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 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
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- UPQZOUHVTJNGFK-UHFFFAOYSA-N diethyl 2-methylpropanedioate Chemical compound CCOC(=O)C(C)C(=O)OCC UPQZOUHVTJNGFK-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- SBUXRMKDJWEXRL-ZWKOTPCHSA-N trans-body Chemical compound O=C([C@@H]1N(C2=O)[C@H](C3=C(C4=CC=CC=C4N3)C1)CC)N2C1=CC=C(F)C=C1 SBUXRMKDJWEXRL-ZWKOTPCHSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RVHKUTDLPVBBEE-UHFFFAOYSA-N 2-amino-N-(1-diphenoxyphosphorylethyl)acetamide Chemical compound C=1C=CC=CC=1OP(=O)(C(NC(=O)CN)C)OC1=CC=CC=C1 RVHKUTDLPVBBEE-UHFFFAOYSA-N 0.000 description 1
- MMJYSVRCFSCVCI-UHFFFAOYSA-N 4-chloro-2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC(Cl)=CC=C1C(Cl)=O MMJYSVRCFSCVCI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/455—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation with carboxylic acids or their derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
- C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
- C07C49/427—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings
- C07C49/433—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having two rings the condensed ring system containing seven carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
- C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3029202A JPH04247052A (ja) | 1991-01-31 | 1991-01-31 | ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法 |
| EP92904250A EP0576673B1 (en) | 1991-01-31 | 1992-01-29 | Bicyclo 4.1.0]heptane-2,4-dione derivative, intermediate for the synthesis thereof, and production thereof |
| US08/117,158 US5468905A (en) | 1991-01-31 | 1992-01-29 | Bicyclo[4,1,0]heptane-2,4-dion derivatives, its synthetic intermediates and process for the manufacture thereof |
| PCT/JP1992/000084 WO1992013821A1 (en) | 1991-01-31 | 1992-01-29 | Bicyclo[4.1.0]heptane-2,4-dione derivative, intermediate for the synthesis thereof, and production thereof |
| DE69211685T DE69211685T2 (de) | 1991-01-31 | 1992-01-29 | Bicyclo(4.1.0)heptan-2,4-dionderivat, zwischenprodukt zur synthese sowie verfahren zur herstellung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3029202A JPH04247052A (ja) | 1991-01-31 | 1991-01-31 | ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH04247052A true JPH04247052A (ja) | 1992-09-03 |
Family
ID=12269610
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3029202A Pending JPH04247052A (ja) | 1991-01-31 | 1991-01-31 | ビシクロ〔４，１，０〕ヘプタン−２，４−ジオン誘導体、その製造法 |
Country Status (5)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993020035A1 (en) * | 1992-04-03 | 1993-10-14 | Nippon Soda Co., Ltd. | Process for producing cyclopropane derivative |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4427995A1 (de) * | 1994-08-08 | 1996-02-15 | Basf Ag | Saccharinderivate |
| CZ268198A3 (cs) * | 1996-02-24 | 1999-02-17 | Basf Aktiengesellschaft | 2-hetaroylcyklohexan- 1,3-diony, způsob jejich výroby a jejich použití |
| EP1417170A1 (de) * | 2001-08-08 | 2004-05-12 | Basf Aktiengesellschaft | Benzoylcyclohexenon-derivate |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL174940C (nl) * | 1973-03-14 | 1984-09-03 | Stamicarbon | Werkwijze voor de bereiding van cyclohexaan-1,3-dion en alkylgesubstitueerde derivaten hiervan. |
| CH653665A5 (de) * | 1981-05-27 | 1986-01-15 | Lonza Ag | Verfahren zur herstellung von dimedon. |
| US4399310A (en) * | 1981-09-18 | 1983-08-16 | Koppers Company, Inc. | Preparation of 1,3-cyclic diones by vapor phase cyclization of delta-keto carboxylic acid esters utilizing carrier condensable under ambient conditions |
| ZA847256B (en) * | 1983-09-16 | 1986-04-30 | Stauffer Chemical Co | Certain 2-(2-substituted benzoyl)-1,3-cyclohexanediones |
| JPS63139146A (ja) * | 1986-10-16 | 1988-06-10 | ストウフアー・ケミカル・カンパニー | ２−（２−置換ベンゾイル）−４−（置換イミノ、オキシイミノ、或はカルボニル）−１，３−シクロヘキサンジオン類 |
| HUT50312A (en) * | 1988-02-01 | 1990-01-29 | Sandoz Ag | Herbicide composition containing new dion-compounds and process for producing these compounds |
| ATE119146T1 (de) * | 1989-07-04 | 1995-03-15 | Nippon Soda Co | Substituierte bicycloheptadionderivate. |
-
1991
- 1991-01-31 JP JP3029202A patent/JPH04247052A/ja active Pending
-
1992
- 1992-01-29 EP EP92904250A patent/EP0576673B1/en not_active Expired - Lifetime
- 1992-01-29 DE DE69211685T patent/DE69211685T2/de not_active Expired - Fee Related
- 1992-01-29 US US08/117,158 patent/US5468905A/en not_active Expired - Fee Related
- 1992-01-29 WO PCT/JP1992/000084 patent/WO1992013821A1/ja active IP Right Grant
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993020035A1 (en) * | 1992-04-03 | 1993-10-14 | Nippon Soda Co., Ltd. | Process for producing cyclopropane derivative |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0576673A4 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1994-02-02 |
| DE69211685D1 (de) | 1996-07-25 |
| US5468905A (en) | 1995-11-21 |
| WO1992013821A1 (en) | 1992-08-20 |
| DE69211685T2 (de) | 1996-12-05 |
| EP0576673A1 (en) | 1994-01-05 |
| EP0576673B1 (en) | 1996-06-19 |
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