GB825907A - A novel dodecahydro-phenanthrene derivative and a process for the manufacture thereof - Google Patents
A novel dodecahydro-phenanthrene derivative and a process for the manufacture thereofInfo
- Publication number
- GB825907A GB825907A GB5660/58A GB566058A GB825907A GB 825907 A GB825907 A GB 825907A GB 5660/58 A GB5660/58 A GB 5660/58A GB 566058 A GB566058 A GB 566058A GB 825907 A GB825907 A GB 825907A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxy
- acetyl
- ethylenedioxyethyl
- resulting
- hydrolysing
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
- C07C25/18—Polycyclic aromatic halogenated hydrocarbons
- C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C13/00—Cyclic hydrocarbons containing rings other than, or in addition to, six-membered aromatic rings
- C07C13/28—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof
- C07C13/32—Polycyclic hydrocarbons or acyclic hydrocarbon derivatives thereof with condensed rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C46/00—Preparation of quinones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/26—Phenanthrenes; Hydrogenated phenanthrenes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/52—Ortho- or ortho- and peri-condensed systems containing five condensed rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 2 - acetyl - 7- oxo - 1,2,3,4,4a,4b,5,6,7,9,10,10a - dodecahydrophenanthrene of the formula <FORM:0825907/IV (b)/1> and the preparation thereof by reacting 1-vinyl-6-methoxy-3,4-dihydronaphthalene with methyl vinyl ketone, e.g. in an inert solvent such as a lower aliphatic alcohol, a fatty acid or a saturated hydrocarbon, isomerizing the resulting 2 - acetyl - 7 - methoxy - 1,2,3,9,10,10a - hexahydro-phenanthrene in acid solution, e.g. in an inert solvent using dry hydrogen chloride, ketalizing the 2-acetyl-7-methoxy-1,2,3,4,9,10-hexahydrophenanthrene so obtained with ethylene glycol, and either reducing the resulting 2 - (11 - ethylenedioxyethyl) - 7 - methoxy - 1,2,3,4,9,10 - hexahydrophenanthrene in liquid ammonia with lithium and an alcohol at low temperature and hydrolysing the so-formed 2 - (11 - ethylenedioxyethyl) - 7 - methoxy - 1,2,3,4,4a,5,8,9,10,10a - decahydrophenanthrene in acid solution or reducing the same in liquid ammonia with potassium and ammonium chloride at low temperature, hydrolysing the resulting 2 - (11 - ethylenedioxyethyl) - 7 - methoxy - 1,2,3,4,4a,9,10,10a - octahydrophenanthrene to form 2-acetyl-7-methoxy-1,2,3,4,4a,9,10,10a-octahydrophenanthrene, ketalizing this compound with ethylene-glycol to form the cyclic ketal thereof, reducing the resulting ketal in liquid ammonia with lithium and an alcohol at a low temperature and hydrolysing the so-formed 2 - (11 - ethylenedioxyethyl) - 7 - methoxy - 1,2,3,4,4a,5,8,9,10,10a - decahydrophenanthrene. A detailed example is given.ALSO:A therapeutic composition, which may be administered orally or parenterally, contains as the active ingredient 2-acetyl-7-oxo-1,2,3,4, 4a,4b,5,6,7,9,10,10a - dodecahydrophenanthrene of the formula <FORM:0825907/VI/1> Thus the composition may be in the form of a tablet, syrup, elixir or injectable solution.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US825907XA | 1957-02-21 | 1957-02-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB825907A true GB825907A (en) | 1959-12-23 |
Family
ID=22172135
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5660/58A Expired GB825907A (en) | 1957-02-21 | 1958-02-21 | A novel dodecahydro-phenanthrene derivative and a process for the manufacture thereof |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB825907A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503545A (en) * | 2018-11-30 | 2019-03-22 | 彩客化学(沧州)有限公司 | A kind of preparation method of 1,4- cyclohexanedione monoethylene acetal |
-
1958
- 1958-02-21 GB GB5660/58A patent/GB825907A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109503545A (en) * | 2018-11-30 | 2019-03-22 | 彩客化学(沧州)有限公司 | A kind of preparation method of 1,4- cyclohexanedione monoethylene acetal |
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