ES255182A1 - Un procedimiento para preparar trioxo-octahidroantracenos y octahidronaftacenos sustituidos - Google Patents
Un procedimiento para preparar trioxo-octahidroantracenos y octahidronaftacenos sustituidosInfo
- Publication number
- ES255182A1 ES255182A1 ES0255182A ES255182A ES255182A1 ES 255182 A1 ES255182 A1 ES 255182A1 ES 0255182 A ES0255182 A ES 0255182A ES 255182 A ES255182 A ES 255182A ES 255182 A1 ES255182 A1 ES 255182A1
- Authority
- ES
- Spain
- Prior art keywords
- chloro
- oxo
- prepared
- tetrahydro
- acid
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 238000006798 ring closing metathesis reaction Methods 0.000 abstract 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- HKGXTOYARVUWQO-UHFFFAOYSA-N 1,2,3,4,4a,5,5a,6-octahydrotetracene Chemical class C1=CC=C2CC(CC3C(CCCC3)=C3)C3=CC2=C1 HKGXTOYARVUWQO-UHFFFAOYSA-N 0.000 abstract 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 150000001454 anthracenes Chemical class 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical group 0.000 abstract 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 2
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 2
- 239000012312 sodium hydride Substances 0.000 abstract 2
- SDGMUBWPXBSKCT-UHFFFAOYSA-N 1-chloro-4-methoxy-2-methylbenzene Chemical compound COC1=CC=C(Cl)C(C)=C1 SDGMUBWPXBSKCT-UHFFFAOYSA-N 0.000 abstract 1
- PRPINYUDVPFIRX-UHFFFAOYSA-N 1-naphthaleneacetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CC=CC2=C1 PRPINYUDVPFIRX-UHFFFAOYSA-N 0.000 abstract 1
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 abstract 1
- FWNPLUAKSHYNJT-UHFFFAOYSA-N 2-(8-chloro-10-methoxy-4-oxo-5-phenylmethoxy-2,3-dihydro-1H-anthracen-1-yl)acetic acid Chemical compound COC1=C2C(=O)CCC(CC(O)=O)C2=CC2=C(Cl)C=CC(OCC3=CC=CC=C3)=C12 FWNPLUAKSHYNJT-UHFFFAOYSA-N 0.000 abstract 1
- LKILPWMVWYSTAV-UHFFFAOYSA-N 2-(8-chloro-5-methoxy-4-oxo-2,3-dihydro-1H-naphthalen-1-yl)acetyl chloride Chemical compound ClC=1C=CC(=C2C(CCC(C12)CC(=O)Cl)=O)OC LKILPWMVWYSTAV-UHFFFAOYSA-N 0.000 abstract 1
- CFBAMZFGESXMKL-UHFFFAOYSA-N 2-(8-chloro-5-methoxy-4-oxo-2,3-dihydro-1H-naphthalen-2-yl)acetaldehyde Chemical compound ClC=1C=CC(=C2C(CC(CC12)CC=O)=O)OC CFBAMZFGESXMKL-UHFFFAOYSA-N 0.000 abstract 1
- OSZLSWCRQXWFTQ-UHFFFAOYSA-N 2-(8-chloro-5-methoxy-4-oxo-2,3-dihydro-1H-naphthalen-2-yl)acetic acid Chemical compound ClC=1C=CC(=C2C(CC(CC12)CC(=O)O)=O)OC OSZLSWCRQXWFTQ-UHFFFAOYSA-N 0.000 abstract 1
- GUUZXORJVABSSF-UHFFFAOYSA-N 2-benzylpentanedioic acid Chemical class OC(=O)CCC(C(O)=O)CC1=CC=CC=C1 GUUZXORJVABSSF-UHFFFAOYSA-N 0.000 abstract 1
- CANKJQUHJPTTNE-UHFFFAOYSA-N 3-[(8-chloro-4-oxo-5-phenylmethoxy-2,3-dihydro-1H-naphthalen-2-yl)methyl]pentanedioic acid Chemical compound ClC=1C=CC(=C2C(CC(CC12)CC(CC(=O)O)CC(=O)O)=O)OCC1=CC=CC=C1 CANKJQUHJPTTNE-UHFFFAOYSA-N 0.000 abstract 1
- FBXMWAWEEWPDQK-UHFFFAOYSA-N 3-[(8-chloro-5-hydroxy-4-oxo-2,3-dihydro-1H-naphthalen-2-yl)methyl]pentanedioic acid Chemical compound ClC=1C=CC(=C2C(CC(CC12)CC(CC(=O)O)CC(=O)O)=O)O FBXMWAWEEWPDQK-UHFFFAOYSA-N 0.000 abstract 1
- 235000011054 acetic acid Nutrition 0.000 abstract 1
- 150000001243 acetic acids Chemical class 0.000 abstract 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 abstract 1
- 239000012346 acetyl chloride Substances 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000004703 alkoxides Chemical class 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 abstract 1
- 229940073608 benzyl chloride Drugs 0.000 abstract 1
- 230000031709 bromination Effects 0.000 abstract 1
- 238000005893 bromination reaction Methods 0.000 abstract 1
- YDVJBLJCSLVMSY-UHFFFAOYSA-N carbamoyl cyanide Chemical group NC(=O)C#N YDVJBLJCSLVMSY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 abstract 1
- 239000008139 complexing agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- DGJMPUGMZIKDRO-UHFFFAOYSA-N cyanoacetamide Chemical compound NC(=O)CC#N DGJMPUGMZIKDRO-UHFFFAOYSA-N 0.000 abstract 1
- XOCWRINMEIMFCW-UHFFFAOYSA-N dimethyl 3-[(8-chloro-4-oxo-5-phenylmethoxy-2,3-dihydro-1H-naphthalen-2-yl)methyl]pentanedioate Chemical compound ClC=1C=CC(=C2C(CC(CC12)CC(CC(=O)OC)CC(=O)OC)=O)OCC1=CC=CC=C1 XOCWRINMEIMFCW-UHFFFAOYSA-N 0.000 abstract 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- UKFXDFUAPNAMPJ-UHFFFAOYSA-N ethylmalonic acid Chemical compound CCC(C(O)=O)C(O)=O UKFXDFUAPNAMPJ-UHFFFAOYSA-N 0.000 abstract 1
- 150000004678 hydrides Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 150000002690 malonic acid derivatives Chemical class 0.000 abstract 1
- 229910021645 metal ion Inorganic materials 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000004702 methyl esters Chemical class 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 abstract 1
- GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US790051A US3002993A (en) | 1959-01-30 | 1959-01-30 | Substituted trioxo-octahydroanthracenes and octahydronaphthacenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES255182A1 true ES255182A1 (es) | 1960-04-16 |
Family
ID=25149498
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES0255182A Expired ES255182A1 (es) | 1959-01-30 | 1960-01-21 | Un procedimiento para preparar trioxo-octahidroantracenos y octahidronaftacenos sustituidos |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3002993A (en, 2012) |
| BE (1) | BE587089A (en, 2012) |
| CH (1) | CH426781A (en, 2012) |
| DK (1) | DK102795C (en, 2012) |
| ES (1) | ES255182A1 (en, 2012) |
| GB (1) | GB927694A (en, 2012) |
| NL (1) | NL247838A (en, 2012) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3219671A (en) * | 1961-04-14 | 1965-11-23 | American Cyanamid Co | Substituted 6-deoxytetracyclines and 6-demethyl-6-deoxytetracyclines |
| BE625366A (en, 2012) * | 1961-11-28 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2744931A (en) * | 1952-10-11 | 1956-05-08 | American Cyanamid Co | Anhydrochlortetracycline |
| US2783261A (en) * | 1953-03-04 | 1957-02-26 | Pfizer & Co C | Polyoxygenated cyclic compounds |
-
0
- NL NL247838D patent/NL247838A/xx unknown
-
1959
- 1959-01-30 US US790051A patent/US3002993A/en not_active Expired - Lifetime
-
1960
- 1960-01-18 GB GB1726/60A patent/GB927694A/en not_active Expired
- 1960-01-21 ES ES0255182A patent/ES255182A1/es not_active Expired
- 1960-01-29 BE BE587089A patent/BE587089A/fr unknown
- 1960-01-29 DK DK34360AA patent/DK102795C/da active
- 1960-01-29 CH CH99260A patent/CH426781A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE587089A (fr) | 1960-05-16 |
| US3002993A (en) | 1961-10-03 |
| GB927694A (en) | 1963-06-06 |
| DK102795C (da) | 1965-10-11 |
| CH426781A (fr) | 1966-12-31 |
| NL247838A (en, 2012) |
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