GB763949A - Polyhydrophenanthrene compounds and their preparation - Google Patents
Polyhydrophenanthrene compounds and their preparationInfo
- Publication number
- GB763949A GB763949A GB34066/55A GB3406655A GB763949A GB 763949 A GB763949 A GB 763949A GB 34066/55 A GB34066/55 A GB 34066/55A GB 3406655 A GB3406655 A GB 3406655A GB 763949 A GB763949 A GB 763949A
- Authority
- GB
- United Kingdom
- Prior art keywords
- keto
- dimethyl
- acid
- ethylenedioxy
- hydrolysis
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises 2,4b-dimethyl-polyhydro phenanthrenes of the formul <FORM:0763949/IV(b)/1> <FORM:0763949/IV(b)/2> (where R represents <FORM:0763949/IV(b)/3> or = O; and in formula I the 7-position is occupied by a divalent group (or a pair of univalent groups) convertible to a keto group by acid hydrolysis; and in formula II by a univalent group convertible to a keto group by acid hydrolysis); the corresponding 7-keto compounds, and processes for the preparation of I and II by (a) ozonizing the corresponding 2-methyl-2-methallyl compounds and reducing the ozonide produced, or (b) treating the corresponding 2 - methyl - 2 - (b : g - dihydroxyisobutyl)-compounds with a glycolsplitting agent, e.g. periodic acid, lead tetraacetate, phenyliodoso acetate. The substituent(s) in position 7, e.g. ethylene ketal, ethylene hemithioketal, dimethyl ketal, or ethyl enol ether, can then be converted to a keto group by hydrolysis with acid. In examples: (1) 2,4b - dimethyl - 2 - methyallyl - 1 - keto - 4 - hydroxy - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6, 7,8,10,10a - dodecahydrophenanthtene in ethyl acetate-methanol is ozonized at - 75 DEG C., the product decomposed with zinc and acetic acid and 2,4b-dimethyl-2-acetonyl-1-keto-4-hydroxy-7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene isolated with ether and purified by chromatography on alumina. Acid hydrolysis yields the corresponding 7-keto compound; (2) 2,4b-dimethyl-2-(b ,g -dihydroxyisobutyl) - 1,4 - diketo - 7 - ethylenedioxy - 1,2,3, 4,4a,4b,5,6,7,8,10,10a-dodecahydrophenanthrene in methanol-pyridine is oxidized with periodic acid to the corresponding 2,4b-dimethyl-2-acetonyl-derivative which is then hydrolysed with acid to the 1,4,7-triketo compound; (3) 2,4b - dimethyl - 2 - (b ,g - dihydroxy-isobutyl) - 1 - keto - 4 - hydroxy - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene is treated as in (2) giving the corresponding 2-acetonyl derivative and on hydrolysis the 1,7-diketo compound. Specification 763,204, 763,208 and 763,950 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US763949XA | 1952-08-30 | 1952-08-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB763949A true GB763949A (en) | 1956-12-19 |
Family
ID=22131732
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB34066/55A Expired GB763949A (en) | 1952-08-30 | 1953-08-21 | Polyhydrophenanthrene compounds and their preparation |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB763949A (en) |
-
1953
- 1953-08-21 GB GB34066/55A patent/GB763949A/en not_active Expired
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