GB1306244A - - Google Patents
Info
- Publication number
- GB1306244A GB1306244A GB4058970A GB4058970A GB1306244A GB 1306244 A GB1306244 A GB 1306244A GB 4058970 A GB4058970 A GB 4058970A GB 4058970 A GB4058970 A GB 4058970A GB 1306244 A GB1306244 A GB 1306244A
- Authority
- GB
- United Kingdom
- Prior art keywords
- adamantyl
- reaction
- prepared
- ethane
- methoxyphenyl
- 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
- 238000006243 chemical reaction Methods 0.000 abstract 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 6
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 abstract 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- -1 benzene compound Chemical class 0.000 abstract 3
- 230000005494 condensation Effects 0.000 abstract 3
- 238000009833 condensation Methods 0.000 abstract 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 abstract 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 3
- KMMVASCGYGKYEI-UHFFFAOYSA-N 1-[bromo-(4-methoxyphenyl)methyl]-4-methoxybenzene Chemical compound C1=CC(OC)=CC=C1C(Br)C1=CC=C(OC)C=C1 KMMVASCGYGKYEI-UHFFFAOYSA-N 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 abstract 2
- 239000007818 Grignard reagent Substances 0.000 abstract 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 abstract 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 abstract 2
- DZULQZKFBAHSRX-UHFFFAOYSA-N adamantane-1-carbaldehyde Chemical compound C1C(C2)CC3CC2CC1(C=O)C3 DZULQZKFBAHSRX-UHFFFAOYSA-N 0.000 abstract 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 abstract 2
- 238000003379 elimination reaction Methods 0.000 abstract 2
- 150000004795 grignard reagents Chemical class 0.000 abstract 2
- JBFYUZGYRGXSFL-UHFFFAOYSA-N imidazolide Chemical compound C1=C[N-]C=N1 JBFYUZGYRGXSFL-UHFFFAOYSA-N 0.000 abstract 2
- 239000011777 magnesium Substances 0.000 abstract 2
- 229910052749 magnesium Inorganic materials 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- VYMPLPIFKRHAAC-UHFFFAOYSA-N 1,2-ethanedithiol Chemical compound SCCS VYMPLPIFKRHAAC-UHFFFAOYSA-N 0.000 abstract 1
- DIVQLVHVBIQZCX-UHFFFAOYSA-N 1-(1-adamantyl)-2,2-bis(4-methoxyphenyl)ethanone Chemical compound C12(CC3CC(CC(C1)C3)C2)C(=O)C(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC DIVQLVHVBIQZCX-UHFFFAOYSA-N 0.000 abstract 1
- SHRFSUUHTIYCGS-UHFFFAOYSA-N 1-(2-adamantyl)-2,2-bis(4-methoxyphenyl)ethanone Chemical compound C12C(C3CC(CC(C1)C3)C2)C(=O)C(C2=CC=C(C=C2)OC)C2=CC=C(C=C2)OC SHRFSUUHTIYCGS-UHFFFAOYSA-N 0.000 abstract 1
- RLRBYCAVZBQANU-UHFFFAOYSA-N 1-(bromomethyl)adamantane Chemical compound C1C(C2)CC3CC2CC1(CBr)C3 RLRBYCAVZBQANU-UHFFFAOYSA-N 0.000 abstract 1
- WMSOXJBCEGWIQV-UHFFFAOYSA-N 1-[2,2-dibromo-2-(4-methoxyphenyl)ethyl]adamantane Chemical compound BrC(CC12CC3CC(CC(C1)C3)C2)(C2=CC=C(C=C2)OC)Br WMSOXJBCEGWIQV-UHFFFAOYSA-N 0.000 abstract 1
- VHPXXRPMERWMLT-UHFFFAOYSA-N 1-[2,2-diiodo-2-(4-methoxyphenyl)ethyl]adamantane Chemical compound IC(CC12CC3CC(CC(C1)C3)C2)(C2=CC=C(C=C2)OC)I VHPXXRPMERWMLT-UHFFFAOYSA-N 0.000 abstract 1
- NDQLATFKOXRKEH-UHFFFAOYSA-N 1-[2-(4-methoxyphenyl)ethyl]adamantane Chemical compound C1=CC(OC)=CC=C1CCC1(C2)CC(C3)CC2CC3C1 NDQLATFKOXRKEH-UHFFFAOYSA-N 0.000 abstract 1
- JCUYQPMSTIALNF-UHFFFAOYSA-N 1-[2-iodo-2-(4-methoxyphenyl)ethenyl]adamantane Chemical group IC(=CC12CC3CC(CC(C1)C3)C2)C2=CC=C(C=C2)OC JCUYQPMSTIALNF-UHFFFAOYSA-N 0.000 abstract 1
- DIVAPEOWCSENNN-UHFFFAOYSA-M 1-adamantylmethyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C1C(C2)CC(C3)CC2CC13C[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 DIVAPEOWCSENNN-UHFFFAOYSA-M 0.000 abstract 1
- BLQURGBJSSSGAU-UHFFFAOYSA-N 2-(1-adamantyl)acetaldehyde Chemical compound C1C(C2)CC3CC2CC1(CC=O)C3 BLQURGBJSSSGAU-UHFFFAOYSA-N 0.000 abstract 1
- JOVAVHRMZHYOFZ-UHFFFAOYSA-N 3,7-dimethoxythiopyrano[3,2-b]chromene Chemical compound COC1=CSC2=CC3=CC=C(C=C3OC2=C1)OC JOVAVHRMZHYOFZ-UHFFFAOYSA-N 0.000 abstract 1
- WFUDMQYKTSWADB-UHFFFAOYSA-N 4-[2-(1-adamantyl)-1-(4-hydroxyphenyl)ethyl]phenol Chemical compound OC1=CC=C(C=C1)C(CC12CC3CC(CC(C1)C3)C2)C2=CC=C(C=C2)O WFUDMQYKTSWADB-UHFFFAOYSA-N 0.000 abstract 1
- QJPJQTDYNZXKQF-UHFFFAOYSA-N 4-bromoanisole Chemical compound COC1=CC=C(Br)C=C1 QJPJQTDYNZXKQF-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- 239000005977 Ethylene Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 241000124008 Mammalia Species 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 abstract 1
- JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 abstract 1
- VGBBJZYOAOCLLS-UHFFFAOYSA-N adamantane-2-carbaldehyde Chemical compound C1C(C2)CC3CC1C(C=O)C2C3 VGBBJZYOAOCLLS-UHFFFAOYSA-N 0.000 abstract 1
- UNGMXQVELCJRIH-UHFFFAOYSA-N adamantane-2-carboxylic acid Chemical compound C1C(C2)CC3CC1C(C(=O)O)C2C3 UNGMXQVELCJRIH-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 238000005661 deetherification reaction Methods 0.000 abstract 1
- 150000004252 dithioacetals Chemical class 0.000 abstract 1
- 230000008030 elimination Effects 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- IBFALXUPJVJGHX-UHFFFAOYSA-N ethyl 2,2-bis[4-(2-ethoxyethoxy)phenyl]acetate Chemical compound C(C)OCCOC1=CC=C(C=C1)C(C(=O)OCC)C1=CC=C(C=C1)OCCOCC IBFALXUPJVJGHX-UHFFFAOYSA-N 0.000 abstract 1
- UQQNVEPAFVPKIM-UHFFFAOYSA-N ethyl 3-(1-adamantyl)-3-hydroxy-2,2-bis(4-hydroxyphenyl)propanoate Chemical compound OC1=CC=C(C=C1)C(C(=O)OCC)(C(C12CC3CC(CC(C1)C3)C2)O)C2=CC=C(C=C2)O UQQNVEPAFVPKIM-UHFFFAOYSA-N 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 abstract 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000012280 lithium aluminium hydride Substances 0.000 abstract 1
- MZIVXJGBKLZCKF-UHFFFAOYSA-N methyl 2-(1-adamantyl)acetate Chemical compound C1C(C2)CC3CC2CC1(CC(=O)OC)C3 MZIVXJGBKLZCKF-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000546 pharmaceutical excipient Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 150000004714 phosphonium salts Chemical class 0.000 abstract 1
- 230000035935 pregnancy Effects 0.000 abstract 1
- 238000007127 saponification reaction Methods 0.000 abstract 1
- 229910000029 sodium carbonate Inorganic materials 0.000 abstract 1
- 235000009518 sodium iodide Nutrition 0.000 abstract 1
- 239000001117 sulphuric acid Substances 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
- C07C43/21—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
- C07D335/12—Thioxanthenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85290669A | 1969-08-25 | 1969-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1306244A true GB1306244A (enExample) | 1973-02-07 |
Family
ID=25314538
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4058970A Expired GB1306244A (enExample) | 1969-08-25 | 1970-08-24 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US3663602A (enExample) |
| JP (1) | JPS5012432B1 (enExample) |
| AU (1) | AU1911070A (enExample) |
| BE (1) | BE755235A (enExample) |
| CH (1) | CH544049A (enExample) |
| DE (1) | DE2041908A1 (enExample) |
| ES (1) | ES382993A1 (enExample) |
| FR (1) | FR2068517B1 (enExample) |
| GB (1) | GB1306244A (enExample) |
| IL (1) | IL35160A0 (enExample) |
| NL (1) | NL7012480A (enExample) |
| ZA (1) | ZA705794B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE795743A (fr) * | 1972-03-15 | 1973-06-18 | Politechnika Warszawska | Procede de preparation de feuilles et de revetements a base de polyarylates, et produits obtenus |
| US4139721A (en) * | 1978-05-01 | 1979-02-13 | General Electric Company | Process for preparing diphenyl haloethylenes |
| US5157164A (en) * | 1990-07-10 | 1992-10-20 | Copolymer Rubber & Chemical Corp. | Polymerizable antioxidant composition |
| US5017727A (en) * | 1990-07-10 | 1991-05-21 | Copolymer Rubber & Chemical Corporation | Polymerizable antioxidant composition |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL6716437A (enExample) * | 1967-12-02 | 1969-06-04 |
-
0
- BE BE755235D patent/BE755235A/xx unknown
-
1969
- 1969-08-25 US US852906A patent/US3663602A/en not_active Expired - Lifetime
-
1970
- 1970-08-24 CH CH1270770A patent/CH544049A/de not_active IP Right Cessation
- 1970-08-24 NL NL7012480A patent/NL7012480A/xx unknown
- 1970-08-24 AU AU19110/70A patent/AU1911070A/en not_active Expired
- 1970-08-24 GB GB4058970A patent/GB1306244A/en not_active Expired
- 1970-08-24 ES ES382993A patent/ES382993A1/es not_active Expired
- 1970-08-24 DE DE19702041908 patent/DE2041908A1/de active Pending
- 1970-08-24 ZA ZA705794A patent/ZA705794B/xx unknown
- 1970-08-24 IL IL35160A patent/IL35160A0/xx unknown
- 1970-08-25 JP JP45073908A patent/JPS5012432B1/ja active Pending
- 1970-08-25 FR FR7031057A patent/FR2068517B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AU1911070A (en) | 1972-03-02 |
| ES382993A1 (es) | 1973-05-01 |
| US3663602A (en) | 1972-05-16 |
| DE2041908A1 (de) | 1971-03-04 |
| FR2068517A1 (enExample) | 1971-08-27 |
| ZA705794B (en) | 1971-04-28 |
| NL7012480A (enExample) | 1971-03-01 |
| CH544049A (de) | 1973-11-15 |
| IL35160A0 (en) | 1970-10-30 |
| JPS5012432B1 (enExample) | 1975-05-12 |
| FR2068517B1 (enExample) | 1973-12-21 |
| BE755235A (fr) | 1971-02-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |