JPH0136455B2 - - Google Patents
Info
- Publication number
- JPH0136455B2 JPH0136455B2 JP56032866A JP3286681A JPH0136455B2 JP H0136455 B2 JPH0136455 B2 JP H0136455B2 JP 56032866 A JP56032866 A JP 56032866A JP 3286681 A JP3286681 A JP 3286681A JP H0136455 B2 JPH0136455 B2 JP H0136455B2
- Authority
- JP
- Japan
- Prior art keywords
- boiling point
- general formula
- elemental analysis
- distilled
- residue
- 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.)
- Expired
Links
- -1 ethylenedioxy Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- 150000001875 compounds Chemical class 0.000 description 27
- 238000004519 manufacturing process Methods 0.000 description 23
- 238000009835 boiling Methods 0.000 description 18
- 238000000921 elemental analysis Methods 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000000259 anti-tumor effect Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 230000000144 pharmacologic effect Effects 0.000 description 4
- 229910052700 potassium Inorganic materials 0.000 description 4
- 239000011591 potassium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003266 anti-allergic effect Effects 0.000 description 3
- 230000003356 anti-rheumatic effect Effects 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 230000003908 liver function Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- WZWQNWWFCHNJON-UHFFFAOYSA-N 1,4-dioxaspiro[4.5]decane-8-carbonitrile Chemical compound C1CC(C#N)CCC21OCCO2 WZWQNWWFCHNJON-UHFFFAOYSA-N 0.000 description 1
- MNDIARAMWBIKFW-UHFFFAOYSA-N 1-bromohexane Chemical compound CCCCCCBr MNDIARAMWBIKFW-UHFFFAOYSA-N 0.000 description 1
- ZOSBAYFWABIRBV-UHFFFAOYSA-N 1-pentylcyclohexane-1-carboxylic acid Chemical compound CCCCCC1(C(O)=O)CCCCC1 ZOSBAYFWABIRBV-UHFFFAOYSA-N 0.000 description 1
- LYGKSUOGJYYSOI-UHFFFAOYSA-N 2-methoxybuta-1,3-diene Chemical compound COC(=C)C=C LYGKSUOGJYYSOI-UHFFFAOYSA-N 0.000 description 1
- JEKLNUVCTRHZFZ-UHFFFAOYSA-N 2-methylideneoctanenitrile Chemical compound CCCCCCC(=C)C#N JEKLNUVCTRHZFZ-UHFFFAOYSA-N 0.000 description 1
- NYEWPZJBNOUNPM-UHFFFAOYSA-N 4-butylcyclohex-2-en-1-one Chemical compound CCCCC1CCC(=O)C=C1 NYEWPZJBNOUNPM-UHFFFAOYSA-N 0.000 description 1
- FNINZFBHAGYQLF-UHFFFAOYSA-N 4-oxo-1-pentylcyclohexane-1-carbonitrile Chemical compound CCCCCC1(C#N)CCC(=O)CC1 FNINZFBHAGYQLF-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 238000005698 Diels-Alder reaction Methods 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000340 anti-metabolite Effects 0.000 description 1
- 229940100197 antimetabolite Drugs 0.000 description 1
- 239000002256 antimetabolite Substances 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 150000001934 cyclohexanes Chemical class 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 231100000957 no side effect Toxicity 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003627 tricarboxylic acid derivatives Chemical class 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3286681A JPS57145834A (en) | 1981-03-05 | 1981-03-05 | Novel cyclohexane derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3286681A JPS57145834A (en) | 1981-03-05 | 1981-03-05 | Novel cyclohexane derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57145834A JPS57145834A (en) | 1982-09-09 |
| JPH0136455B2 true JPH0136455B2 (enrdf_load_stackoverflow) | 1989-07-31 |
Family
ID=12370772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3286681A Granted JPS57145834A (en) | 1981-03-05 | 1981-03-05 | Novel cyclohexane derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57145834A (enrdf_load_stackoverflow) |
-
1981
- 1981-03-05 JP JP3286681A patent/JPS57145834A/ja active Granted
Non-Patent Citations (1)
| Title |
|---|
| J.AM.CHEM.SOC=1979 * |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57145834A (en) | 1982-09-09 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JPH0149695B2 (enrdf_load_stackoverflow) | ||
| JP2825596B2 (ja) | 置換キノリンの逐次酸化による置換ピリジン―２，３―ジカルボン酸の製造法 | |
| JP4991744B2 (ja) | ビフェニル類の製造法 | |
| JPH0136455B2 (enrdf_load_stackoverflow) | ||
| PL118827B1 (en) | Method of manufacture of tricyclicdiketone | |
| RU2264391C2 (ru) | Способ получения производного хинолинкарбоксальдегида и промежуточных соединений | |
| JP4474773B2 (ja) | （ｐ−クロロフェニル）プロパノール誘導体の製造法 | |
| JP3386596B2 (ja) | ５（ｅ），８（ｚ），１１（ｚ）−テトラデカトリエン−２−オンの製造方法 | |
| JP2003155259A (ja) | 芳香族アルデヒドの製造方法および新規な芳香族ジアルデヒド | |
| HU195659B (en) | Process for producing cotarnine | |
| JPH082844B2 (ja) | フェネチルアミン類の製造方法 | |
| JPH027583B2 (enrdf_load_stackoverflow) | ||
| JPS63170335A (ja) | ｄｌ−ｃｉｓ−菊酸の先駆物質の合成法 | |
| JPH0523255B2 (enrdf_load_stackoverflow) | ||
| EP0144484A1 (en) | Dicyclopentadiene dicarboxylic acid derivatives and process for their preparation | |
| JPS6122058A (ja) | ３−（４−フルオロフエノキシ）プロピオニトリル及び該化合物を用いる６−フルオロ−４−クロマノンの製造法 | |
| JPH03215472A (ja) | 新規な４―置換―３，５―ジメチルピコリン酸化合物およびその製造方法 | |
| JP3047338B2 (ja) | α−メルカプトフロロアルキルカルボン酸と２−メルカプトフロロアルキルアルコールおよびそれらの製造方法 | |
| JPS6348269B2 (enrdf_load_stackoverflow) | ||
| SU493964A3 (ru) | Способ производных изоиндолина или их солей | |
| JPH0522713B2 (enrdf_load_stackoverflow) | ||
| JPS6219419B2 (enrdf_load_stackoverflow) | ||
| JPS6051471B2 (ja) | ３，４−ジヒドロカルボスチリル誘導体 | |
| JPH02304066A (ja) | ４―ヒドロキシ―６―ポリフルオロアルキルピリミジンの製造方法 | |
| JPS61227578A (ja) | １，３，２―ジオキサチオラン―２―オキシド誘導体およびその製法 |