GB777681A - Polyhydrophenanthrene compounds - Google Patents
Polyhydrophenanthrene compoundsInfo
- Publication number
- GB777681A GB777681A GB23130/53A GB2313053A GB777681A GB 777681 A GB777681 A GB 777681A GB 23130/53 A GB23130/53 A GB 23130/53A GB 2313053 A GB2313053 A GB 2313053A GB 777681 A GB777681 A GB 777681A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- dodecahydrophenanthrene
- methallyl
- compounds
- ethylenedioxy
- 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 compounds of the formul : <FORM:0777681/IV(b)/1> <FORM:0777681/IV(b)/2> wherein R is hydroxyl or keto, R1 is an unsaturated aliphatic hydrocarbon radical, and R11 is a substituted or unsubstituted unsaturated aliphatic hydrocarbon radical, and which contain in position 7 in I either a divalent group or a pair of univalent groups which yield a keto group on acid hydrolysis, and in II a single univalent group convertible to keto on acid hydrolysis. The invention also comprises the corresponding 7-keto compounds (III), their preparation by acid hydrolysis of compounds I or II, and a process for the preparation of compounds having in ring C the structure: <FORM:0777681/IV(b)/3> by reacting the corresponding 1-keto compounds with an unsaturated aliphatic metallo-organic compound, and hydrolysing the reaction product. Rings A and B can be substituted by hydroxy, acyloxy, alkyl, ether and ketal groups. Specified groups in the 7-position of compounds I and II are ethylene dioxy, ethylene dithioketal, ethylene hemi-thioketal, dimethyl ketal or ethyl enol ether. In examples: (1) 2,4b - dimethyl - 2 - methallyl - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene - 1,4 - dione (IV) is added to ethoxyacetylene magnesium bromide in benzene and the product decomposed with ice-water, yielding 1-ethoxyethinyl - 2,4b - dimethyl - 2-methallyl - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene - 1 - ol-4-one. Similarly, using a stereoisomer of IV, two stereochemical modifications of the 1-ethoxyethinyl derivative are obtained. (2) 2,4b-dimethyl - 2 - methallyl - 7 - ethylenedioxy-1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene - 1 - one - 4 - ol (V) is treated as in (1) to give the corresponding 1-ethoxyethinyl-1,4-diol. (3) Treatment of V with ethereal allyl magnesium bromide gives the corresponding 1-allyl-1,4-diol, which after acid hydrolysis yields 1 - allyl - 2,4b - dimethyl - 2 - methallyl - 1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene 1,4-diol-7-one. (4) Treatment of IV with lithium or potassium acetylide in liquid ammonia, or with acetylene and potassium in t-butanolbenzene gives 1 - ethinyl - 2,4b - dimethyl - 2-methallyl - 7 - ethylenedioxy - 1,2,3,4,4a,4b,5,6,7,8,10,10a - dodecahydrophenanthrene - 1 - ol- 4 - one. (5) Oxidation of the 1 - allyl - 7-ethylenedioxy - 1,4 - diol obtained in (3), using chromium trioxide-pyridine, produces the corresponding 1-ol-4-one, which is then hydrolysed with acid to 1-allyl-2,4b-dimethyl-2-methallyl-1,2,3,4,4a,4b,5,6,7,9,10,10a - dodecahydrophenanthrene - 1 - ol - 4,7 - dione. Specifications 763,204 and 763,208 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US777681XA | 1952-09-05 | 1952-09-05 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB777681A true GB777681A (en) | 1957-06-26 |
Family
ID=22139935
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB23130/53A Expired GB777681A (en) | 1952-09-05 | 1953-08-21 | Polyhydrophenanthrene compounds |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB777681A (en) |
-
1953
- 1953-08-21 GB GB23130/53A patent/GB777681A/en not_active Expired
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