GB805607A - New hydrophenanthrene compounds - Google Patents
New hydrophenanthrene compoundsInfo
- Publication number
- GB805607A GB805607A GB23783/57A GB2378357A GB805607A GB 805607 A GB805607 A GB 805607A GB 23783/57 A GB23783/57 A GB 23783/57A GB 2378357 A GB2378357 A GB 2378357A GB 805607 A GB805607 A GB 805607A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methallyl
- group
- allyl
- methyl
- compounds
- 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
Abstract
The invention comprises polyhydrophenanthrene compounds of the formula <FORM:0805607/IV (b)/1> in which R is an alkyl group of at most eight carbon atoms and X1 is a ketalized oxo group, R1 is a hydrogen atom or a methyl group, and X is an oxo or hydroxy group. The compounds are prepared by introducing an allyl or methallyl group into the 2-position of the corresponding 1-keto-polyhydrophenanthrenes bearing in the 2-position only a carbo-alkoxy group, preferably by means of an allyl or methallyl halide in the presence of an alkaline condensing agent such as alkali metal alcoholates, amides, hydrides or carbonates or quaternary ammonium bases. The keto group in the 1-position may subsequently be reduced with a complex hydride of boron, e.g. sodium borohydride, to give the corresponding 1-ol. In examples: (1) 4bb - methyl - 2 - carbethoxy - 4b - ethoxycarboxy - 7 - ethylenedioxy - 1,2,3,4,4aa ,4b,5,6,7,8, 10,10ab - dodecahydrophenanthrene - 1 - one in dioxane is treated under nitrogen with sodium hydride and then methallyl iodide yielding a mixture of two 4bb -methyl-2-carbethoxy-2-methallyl - 4b - ethoxycarboxy - 7 - ethylenedioxy - 1,2,3,4,4aa ,4b,5,6,7,8,10,10ab - dodecahydrophenanthrene - 1 - ones, isomeric at carbon atom 2; (2) as in (1) using methallyl iodide and potassium carbonate, and separating the isomeric mixture by chromatography on alumina; (3) as in (2) but using allyl iodide (or allyl chloride and KI) to yield the corresponding 2-allyl compounds; (4) 2a -methallyl-2b -carbethoxy - 4b - ethoxycarboxy - 4bb - methyl - 7 - ethylenedioxy - 1,2,3,4,4aa ,4b,5,6,7,8,10,10ab -dodecahydrophenanthrene-1-one is reduced with sodium borohydride in ethanol and the product chromatographed on alumina, giving the corresponding 1-ol compound. Specifications 805,605, 805,606, 805,608 and 805,609 also are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH805607X | 1954-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB805607A true GB805607A (en) | 1958-12-10 |
Family
ID=4538032
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB23783/57A Expired GB805607A (en) | 1954-02-05 | 1955-01-14 | New hydrophenanthrene compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB805607A (en) |
-
1955
- 1955-01-14 GB GB23783/57A patent/GB805607A/en not_active Expired
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