SU497761A3 - Способ получени спиро-бензоциклануксусных кислот - Google Patents
Способ получени спиро-бензоциклануксусных кислотInfo
- Publication number
- SU497761A3 SU497761A3 SU1949760A SU1949760A SU497761A3 SU 497761 A3 SU497761 A3 SU 497761A3 SU 1949760 A SU1949760 A SU 1949760A SU 1949760 A SU1949760 A SU 1949760A SU 497761 A3 SU497761 A3 SU 497761A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acetic acid
- spiro
- benzocyclan
- cyclohexane
- obtaining
- Prior art date
Links
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 title description 10
- 238000000034 method Methods 0.000 title description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- -1 spiro- (cyclohexane-1,1inden) -5-acetic acid Chemical compound 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 150000001243 acetic acids Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- BDRTVPCFKSUHCJ-UHFFFAOYSA-N molecular hydrogen;potassium Chemical compound [K].[H][H] BDRTVPCFKSUHCJ-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JRSDGJVHYMRHMF-UHFFFAOYSA-N spiro[1,2-dihydroindene-3,1'-cyclohexane] Chemical compound C12=CC=CC=C2CCC21CCCCC2 JRSDGJVHYMRHMF-UHFFFAOYSA-N 0.000 description 1
- PEZQQSSHQCXWBQ-UHFFFAOYSA-N spiro[cyclohexane-1,1'-indene] Chemical compound C1CCCCC21C1=CC=CC=C1C=C2 PEZQQSSHQCXWBQ-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
- C07C57/50—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid containing condensed ring systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/46—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing six-membered aromatic rings and other rings, e.g. cyclohexylphenylacetic acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C57/00—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms
- C07C57/52—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen
- C07C57/62—Unsaturated compounds having carboxyl groups bound to acyclic carbon atoms containing halogen containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/42—Unsaturated compounds containing hydroxy or O-metal groups
- C07C59/54—Unsaturated compounds containing hydroxy or O-metal groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/86—Unsaturated compounds containing keto groups containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C59/00—Compounds having carboxyl groups bound to acyclic carbon atoms and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C59/40—Unsaturated compounds
- C07C59/76—Unsaturated compounds containing keto groups
- C07C59/88—Unsaturated compounds containing keto groups containing halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D309/06—Radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/96—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings spiro-condensed with carbocyclic rings or ring systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pain & Pain Management (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Pyrane Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ СПИРО-БЕНЗОЦИКЛАНУКСУСНЫХ
КИСЛОТ
но,,с-н,с
IГ
гидрируют в спиртовой среде в присутствии катализатора - паллади на угле до соединени общей формулы I.
Осуществление способа показано на следующем примере.
Фаза А. 3-Гидроксиспиро-(циклогексан1 ,Г-индан)-5-уксусна кислота.
Раствор ют 7,7 г З-оксоепиро-(циклогексан1 ,1-индан)-5-уксусной кислоты в 70 мл этанола и 7 мл воды и прибавл ют при перемещивании 7,7 г бороводорода кали , поддержива температуру ниже 30-32°С; перемещивают в течение 2,5 час при 22°С, прибавл ют 500 мл воды, затем 25 мл сол ной кислоты и экстрагируют хлористым метиленом; промывают водой органические слои, сущат над сернокислым магнием, фильтруют и перегон ют досуха в вакууме; остаток кристаллизуют в 50 мл изопропилового эфира, фильтруют, промывают осадок изопропиловым эфиром и сушат . Получают 7,2 г 3-гидроксиспиро-(циклогексан 1,Г-индан)-5-уксусной кислоты, плав щейс при 120°С (выход 93%).
Дл анализа продукт перекристаллизовывают в эфире в гор чем и холодном состо нии; температура плавлени остаетс неизменной.
Анализ: С1бН2оОз 260,32.
Вычислено, %: С 73,82; Н 7,74.
Найдено, %: С 73,9; Н 7,7.
ИК-спектр: присутствие ОН спирта при 3581 см-1.
Присутствие кислоты.
УФ-спектр (этанол): перегиб у 217 ммк
jl(
EIC; 1095.
Максимум при 220-221 ммк Eicl, 1160. Перегиб у 227 ммк 930. Максимум при 259-260 ммк 327. Перегиб у 268-269 ммк Eicl, 223. Максимум при 285 ммк EiS. 38. Максимум при 296 ммк EJS, 27.
Фаза В. Спиро-(циклогексан-1,1-индан)5-уксусна кислота.
Раствор ют 4,75 г спиро-(циклогексан-1,1инден )-5-уксусной кислоты в 10 мл этанола и прибавл ют 2,4 г угл с 10% паллади , пропускают поток водорода в течение 20 мин, фильтруют и растворитель отгон ют досуха в вакууме; остаток кристаллизуют в 10 мл н-пентана при -10°С и получают 4,10 г спиро-(циклогексан-1,Г-индан)-5 - уксусной кислоты, плав щейс при 75°С (выход 87%).
Предмет изобретени
Способ получени спиро-бензоциклануксусных кислот общей формулы I
ОО
CH2-Y-(CHj3-C-ORi
- НО - (с«г)4Шз
D
где R - водород, хлор, низший алкоксил, трифторметил,
Y - метиленова группа -(СН)2-, атом кислорода или серы,
п - целое число от 2 до 4, отличающийс тем, что производное уксусной кислоты общей формулы II
Фаза Б. Спиро-(циклогексан-1,1-инден)5-уксусна кислота.
Раствор ют 3 г З-гидроксиспиро-(циклогексан-1 ,1-индан)-5-уксусной кислоты в 90 мл бензола, отгон ют 10 мл растворител , прибавл ют 600 мг ft-толуолсульфокислоты, отгон ют 50 мл растворител ; охлаждают до 20°С, прибавл ют 50 мл воды, экстрагируют эфиром , промывают эфирный слой водой, сущат над сернокислым магнием, фильтруют и отгон ют досуха в вакууме; кристаллизуют остаток в 10 мл н-пентана, фильтруют и промывают н-пентаном; получают 2,52 г спиро-(циклогексан-1 ,Г-инден)-5уксусной кислоты, плав щейс при 100°С (выход 90%).
Дл анализа образец перекристаллизовывают в изопропиловом эфире в гор чем и холодном состо нии; точка плавлени остаетс неизменной .
Анализ: CieHisOa 242,30.
Вычислено, %: С 79,31; Н 7,49.
Найдено, %: С 79,4; Н 7.3.
Н02С-Н,,С
(%)«-/
где R, Y, п имеют выщеуказанные значени , восстанавливают смещанным гидридом до гидроксилированного соединени общей формулы III
где R, Y, п имеют выщеуказанные значени . б5 которое подвергают действию дегидратирую5 щего средства дл получени соединени общей формулы IV нп г-ч 0-, i 2 I и Л 6 где R, Y, п имеют вышеуказанные значени , и последнее обрабатывают гидрирующим агентом в присутствии катализатора с последующим выделением целевого продукта из5вестными приемами.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR696930259A FR2062864B1 (ru) | 1969-09-05 | 1969-09-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU497761A3 true SU497761A3 (ru) | 1975-12-30 |
Family
ID=9039740
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1472070A SU379082A3 (ru) | 1969-09-05 | 1970-08-20 | |
| SU1949743A SU508172A3 (ru) | 1969-09-05 | 1973-08-20 | Способ получени оксоспиробензоциклануксусных кислот |
| SU1949760A SU497761A3 (ru) | 1969-09-05 | 1973-08-20 | Способ получени спиро-бензоциклануксусных кислот |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1472070A SU379082A3 (ru) | 1969-09-05 | 1970-08-20 | |
| SU1949743A SU508172A3 (ru) | 1969-09-05 | 1973-08-20 | Способ получени оксоспиробензоциклануксусных кислот |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3769425A (ru) |
| JP (1) | JPS4925938B1 (ru) |
| AT (1) | AT325033B (ru) |
| BE (1) | BE755747A (ru) |
| CA (1) | CA977761A (ru) |
| CH (3) | CH537893A (ru) |
| DE (1) | DE2043975C2 (ru) |
| DK (1) | DK144472C (ru) |
| ES (1) | ES383398A1 (ru) |
| FR (1) | FR2062864B1 (ru) |
| GB (1) | GB1319998A (ru) |
| IL (1) | IL35136A (ru) |
| NL (1) | NL175408C (ru) |
| OA (1) | OA03477A (ru) |
| SE (1) | SE375996B (ru) |
| SU (3) | SU379082A3 (ru) |
| ZA (1) | ZA705886B (ru) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2199461A2 (en) * | 1972-09-21 | 1974-04-12 | Roussel Uclaf | Analgesic and antiinflammatory spiro cpds - spiro tetrahydro (thia)pyran tetrahydro naphthalene acetic acid derivs |
-
0
- BE BE755747D patent/BE755747A/xx not_active IP Right Cessation
-
1969
- 1969-09-05 FR FR696930259A patent/FR2062864B1/fr not_active Expired
-
1970
- 1970-08-20 SU SU1472070A patent/SU379082A3/ru active
- 1970-08-20 IL IL35136A patent/IL35136A/xx unknown
- 1970-09-03 CH CH491372A patent/CH537893A/fr not_active IP Right Cessation
- 1970-09-03 CH CH1320370A patent/CH533075A/fr not_active IP Right Cessation
- 1970-09-03 CH CH491472A patent/CH539014A/fr not_active IP Right Cessation
- 1970-09-04 SE SE7012067A patent/SE375996B/xx unknown
- 1970-09-04 JP JP45077195A patent/JPS4925938B1/ja active Pending
- 1970-09-04 DE DE2043975A patent/DE2043975C2/de not_active Expired
- 1970-09-04 ES ES383398A patent/ES383398A1/es not_active Expired
- 1970-09-04 GB GB4254470A patent/GB1319998A/en not_active Expired
- 1970-09-04 CA CA092,596A patent/CA977761A/en not_active Expired
- 1970-09-05 OA OA54021A patent/OA03477A/xx unknown
- 1970-09-07 AT AT425972*1A patent/AT325033B/de not_active IP Right Cessation
- 1970-09-07 NL NLAANVRAGE7013179,A patent/NL175408C/xx not_active IP Right Cessation
- 1970-09-07 DK DK457470A patent/DK144472C/da not_active IP Right Cessation
-
1971
- 1971-08-27 ZA ZA705886A patent/ZA705886B/xx unknown
-
1972
- 1972-06-07 US US00260539A patent/US3769425A/en not_active Expired - Lifetime
-
1973
- 1973-08-20 SU SU1949743A patent/SU508172A3/ru active
- 1973-08-20 SU SU1949760A patent/SU497761A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| CA977761A (en) | 1975-11-11 |
| ES383398A1 (es) | 1973-01-16 |
| CH537893A (fr) | 1973-07-31 |
| DK144472C (da) | 1982-09-13 |
| SE375996B (ru) | 1975-05-05 |
| FR2062864A1 (ru) | 1971-07-02 |
| IL35136A0 (en) | 1970-10-30 |
| FR2062864B1 (ru) | 1973-07-13 |
| CH539014A (fr) | 1973-08-31 |
| ZA705886B (en) | 1971-12-29 |
| SU508172A3 (ru) | 1976-03-25 |
| SU379082A3 (ru) | 1973-04-18 |
| DK144472B (da) | 1982-03-15 |
| NL7013179A (ru) | 1971-03-09 |
| OA03477A (fr) | 1971-03-30 |
| DE2043975A1 (de) | 1971-03-11 |
| IL35136A (en) | 1975-06-25 |
| JPS4925938B1 (ru) | 1974-07-04 |
| NL175408C (nl) | 1984-11-01 |
| NL175408B (nl) | 1984-06-01 |
| DE2043975C2 (de) | 1983-01-20 |
| AT325033B (de) | 1975-09-25 |
| US3769425A (en) | 1973-10-30 |
| CH533075A (fr) | 1973-01-31 |
| BE755747A (fr) | 1971-03-04 |
| GB1319998A (en) | 1973-06-13 |
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