CA1045164A - Procede de preparation de nouveaux terpenophenols - Google Patents
Procede de preparation de nouveaux terpenophenolsInfo
- Publication number
- CA1045164A CA1045164A CA224,583A CA224583A CA1045164A CA 1045164 A CA1045164 A CA 1045164A CA 224583 A CA224583 A CA 224583A CA 1045164 A CA1045164 A CA 1045164A
- Authority
- CA
- Canada
- Prior art keywords
- terpenophenols
- formula
- ppm
- preparation
- bromination
- 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
- 238000000034 method Methods 0.000 title claims abstract description 9
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 230000031709 bromination Effects 0.000 claims abstract description 5
- 238000005893 bromination reaction Methods 0.000 claims abstract description 5
- GSQACUNMFGRAKY-UHFFFAOYSA-N bromine;1,4-dioxane Chemical compound [Br].C1COCCO1 GSQACUNMFGRAKY-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 235000007586 terpenes Nutrition 0.000 claims abstract description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
- DTLTUUJDCNTTSN-UHFFFAOYSA-N 1,4-dioxane;molecular bromine Chemical group BrBr.C1COCCO1 DTLTUUJDCNTTSN-UHFFFAOYSA-N 0.000 claims description 5
- 125000004135 2-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C1([H])C([H])([H])C2([H])* 0.000 abstract 1
- -1 5-camphyl Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 13
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 125000003118 aryl group Chemical group 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 3
- 244000052616 bacterial pathogen Species 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920001817 Agar Polymers 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-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
- 238000005481 NMR spectroscopy Methods 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
- 235000010419 agar Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NYYGACIUGBJQHR-UHFFFAOYSA-N 5-methyl-2-(4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl)phenol Chemical compound OC1=CC(C)=CC=C1C1C(C2(C)C)(C)CCC2C1 NYYGACIUGBJQHR-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000588722 Escherichia Species 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 240000004543 Vicia ervilia Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 229960005475 antiinfective agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/12—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings
- C07C39/17—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring polycyclic with no unsaturation outside the aromatic rings containing other rings in addition to the six-membered aromatic rings, e.g. cyclohexylphenol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/01—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis
- C07C37/055—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by replacing functional groups bound to a six-membered aromatic ring by hydroxy groups, e.g. by hydrolysis the substituted group being bound to oxygen, e.g. ether group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/11—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms
- C07C37/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by reactions increasing the number of carbon atoms by addition reactions, i.e. reactions involving at least one carbon-to-carbon unsaturated bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/62—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/42—Halogenated derivatives containing six-membered aromatic rings and other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/18—Preparation of ethers by reactions not forming ether-oxygen bonds
- C07C41/22—Preparation of ethers by reactions not forming ether-oxygen bonds by introduction of halogens; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB16142/74A GB1510302A (en) | 1974-04-11 | 1974-04-11 | Terpenophenols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1045164A true CA1045164A (fr) | 1978-12-26 |
Family
ID=10071943
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA224,583A Expired CA1045164A (fr) | 1974-04-11 | 1975-04-11 | Procede de preparation de nouveaux terpenophenols |
| CA224,571A Expired CA1055529A (en) | 1974-04-11 | 1975-04-11 | Preparation of terpenophenols |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA224,571A Expired CA1055529A (en) | 1974-04-11 | 1975-04-11 | Preparation of terpenophenols |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4067899A (enExample) |
| JP (2) | JPS5830288B2 (enExample) |
| BE (1) | BE827797A (enExample) |
| CA (2) | CA1045164A (enExample) |
| CH (2) | CH593221A5 (enExample) |
| DE (1) | DE2515382A1 (enExample) |
| DK (2) | DK142358B (enExample) |
| FR (1) | FR2267093B1 (enExample) |
| GB (1) | GB1510302A (enExample) |
| IE (1) | IE40910B1 (enExample) |
| LU (2) | LU72250A1 (enExample) |
| NL (2) | NL7504369A (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4301306A (en) * | 1980-03-27 | 1981-11-17 | The B. F. Goodrich Company | Norbornenyl phenolic compounds |
| JPS59116242A (ja) * | 1982-12-22 | 1984-07-05 | Kao Corp | シクロヘキサノ−ル誘導体および香料組成物 |
| DE3369842D1 (en) * | 1983-05-24 | 1987-04-02 | Dow Chemical Co | Bis-(norbornyl or substituted norbornyl) derivatives of a phenol or a phenylamine, process for their preparation and compositions containing same |
| US5382713A (en) * | 1993-02-05 | 1995-01-17 | Shell Oil Company | Phenolic compounds |
| RU2406487C1 (ru) * | 2009-05-06 | 2010-12-20 | Учреждение Российской академии медицинских наук Научно-исследовательский институт фармакологии Сибирского отделения РАМН | Средство, обладающее ретинопротекторной активностью |
| JP5363693B1 (ja) * | 2010-09-28 | 2013-12-11 | プロメラス， エルエルシー | ノルボルナンベースのｐａｃバラスト、及びｐａｃを含むポジティブ型の感光性樹脂組成物 |
| WO2013006098A2 (ru) * | 2011-07-06 | 2013-01-10 | Федеральное Государственное Бюджетное Учреждение Науки Институт Химии Коми Научного Центра Уральского Отделения Российской Академии Наук | Производные 2,6-диизоборнилфенола |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2289550A (en) * | 1940-08-07 | 1942-07-14 | American Cyanamid Co | Nitro bornyl phenols as insecticides |
| US2537647A (en) * | 1948-02-21 | 1951-01-09 | Firestone Tire & Rubber Co | Rearrangement of terpenyl aryl ethers |
| US3878254A (en) * | 1962-11-28 | 1975-04-15 | Marpha Societe A Responsibilit | 6-isoformyl-3,4-xylenol and a process for its preparation |
| FR1355165A (fr) | 1963-04-11 | 1964-03-13 | Wolfen Filmfab Veb | Procédé de préparation de phénols terpéniques et de leurs éthers, et produits obtenus |
| GB1306217A (enExample) * | 1969-07-04 | 1973-02-07 |
-
1974
- 1974-04-11 GB GB16142/74A patent/GB1510302A/en not_active Expired
-
1975
- 1975-04-01 FR FR7510168A patent/FR2267093B1/fr not_active Expired
- 1975-04-02 CH CH415575A patent/CH593221A5/xx not_active IP Right Cessation
- 1975-04-02 CH CH415475A patent/CH593891A5/xx not_active IP Right Cessation
- 1975-04-07 IE IE773/75A patent/IE40910B1/xx unknown
- 1975-04-09 LU LU72250A patent/LU72250A1/xx unknown
- 1975-04-09 LU LU72249A patent/LU72249A1/xx unknown
- 1975-04-09 DE DE19752515382 patent/DE2515382A1/de not_active Withdrawn
- 1975-04-09 US US05/566,364 patent/US4067899A/en not_active Expired - Lifetime
- 1975-04-10 BE BE155288A patent/BE827797A/xx not_active IP Right Cessation
- 1975-04-10 DK DK154175AA patent/DK142358B/da not_active IP Right Cessation
- 1975-04-10 DK DK154075AA patent/DK142170B/da not_active IP Right Cessation
- 1975-04-11 CA CA224,583A patent/CA1045164A/fr not_active Expired
- 1975-04-11 JP JP50043490A patent/JPS5830288B2/ja not_active Expired
- 1975-04-11 NL NL7504369A patent/NL7504369A/xx not_active Application Discontinuation
- 1975-04-11 JP JP50043491A patent/JPS5830289B2/ja not_active Expired
- 1975-04-11 CA CA224,571A patent/CA1055529A/en not_active Expired
- 1975-04-11 NL NL7504368A patent/NL7504368A/xx not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1055529A (en) | 1979-05-29 |
| JPS50151857A (enExample) | 1975-12-06 |
| DK154075A (enExample) | 1975-10-12 |
| LU72250A1 (enExample) | 1975-08-20 |
| FR2267093A1 (enExample) | 1975-11-07 |
| DK154175A (enExample) | 1975-10-12 |
| DK142358C (enExample) | 1981-07-06 |
| LU72249A1 (enExample) | 1975-08-20 |
| DK142358B (da) | 1980-10-20 |
| IE40910L (en) | 1975-10-11 |
| GB1510302A (en) | 1978-05-10 |
| NL7504368A (nl) | 1975-10-14 |
| JPS5830289B2 (ja) | 1983-06-28 |
| FR2267093B1 (enExample) | 1980-02-22 |
| US4067899A (en) | 1978-01-10 |
| JPS5830288B2 (ja) | 1983-06-28 |
| NL7504369A (nl) | 1975-10-14 |
| DK142170C (enExample) | 1981-02-09 |
| IE40910B1 (en) | 1979-09-12 |
| JPS51118753A (en) | 1976-10-18 |
| CH593891A5 (enExample) | 1977-12-30 |
| BE827797A (fr) | 1975-07-31 |
| DK142170B (da) | 1980-09-15 |
| CH593221A5 (enExample) | 1977-11-30 |
| DE2515382A1 (de) | 1975-11-06 |
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