GB975596A - Preparation of steroids and d-homo-steroids related to oestrone - Google Patents
Preparation of steroids and d-homo-steroids related to oestroneInfo
- Publication number
- GB975596A GB975596A GB4056060A GB4056060A GB975596A GB 975596 A GB975596 A GB 975596A GB 4056060 A GB4056060 A GB 4056060A GB 4056060 A GB4056060 A GB 4056060A GB 975596 A GB975596 A GB 975596A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oestrone
- homo
- methyl
- methyl ether
- oestradiol
- 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
- DNXHEGUUPJUMQT-CBZIJGRNSA-N Estrone Chemical compound OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 DNXHEGUUPJUMQT-CBZIJGRNSA-N 0.000 title abstract 4
- 229960003399 estrone Drugs 0.000 title abstract 4
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 title abstract 2
- 150000000795 D-homosteroids Chemical class 0.000 title 1
- 150000003431 steroids Chemical class 0.000 title 1
- VOXZDWNPVJITMN-ZBRFXRBCSA-N 17β-estradiol Chemical compound OC1=CC=C2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 VOXZDWNPVJITMN-ZBRFXRBCSA-N 0.000 abstract 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 3
- 229930182833 estradiol Natural products 0.000 abstract 3
- -1 hydroxymethylene Chemical group 0.000 abstract 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 abstract 2
- 239000005977 Ethylene Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- BCWWDWHFBMPLFQ-VXNCWWDNSA-N (8r,9s,13s,14s)-3-methoxy-13-methyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-17-one Chemical compound C1C[C@]2(C)C(=O)CC[C@H]2[C@@H]2CCC3=CC(OC)=CC=C3[C@H]21 BCWWDWHFBMPLFQ-VXNCWWDNSA-N 0.000 abstract 1
- 239000003377 acid catalyst Substances 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 238000006210 cyclodehydration reaction Methods 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 238000007336 electrophilic substitution reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 150000005217 methyl ethers Chemical class 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J1/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, not substituted in position 17 beta by a carbon atom, e.g. estrane, androstane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Steroid Compounds (AREA)
Abstract
Compounds of formula <FORM:0975596/C1/1> or <FORM:0975596/C1/2> wherein each R is H or alkyl, R1 is alkyl, Q is methylene or ethylene, Y is carbonyl, hydroxymethylene or a group convertible by hydrolysis into carbonyl or hydroxymethylene and E is a group (such as alkoxy, hydroxy, acyloxy, acylamino, amino, monoalkylamino or dialkylamino) which activates the aromatic ring in electrophilic substitution and is predominantly o- and p-directing, are produced by cyclodehydration of a compound of structure <FORM:0975596/C1/3> e.g. by use of an acid catalyst. H in the formula is preferably trans. to R1. In examples, D-homo-8- and -9(11)-dehydro-oestrone methyl ethers (R=H, R1=methyl, Q=ethylene, Y=carbonyl, E=methoxy) were prepared and converted by reduction to O-homo oestradiol methyl ether, which was oxidised to D-homo oestrone methyl ether for identification; the analogous methyl ethers of 9(11)-dehydro-oestrone, oestradiol and oestrone were similarly made. Dehydrooestradiol methyl ether was prepared directly from the starting material in which Y is hydroxymethylene and was hydrogenated to oestradiol methyl ether. Specifications 975,591, 975,592, 975,593 and 975,594 also are referred to.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4056060A GB975596A (en) | 1959-09-25 | 1959-09-25 | Preparation of steroids and d-homo-steroids related to oestrone |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4056060A GB975596A (en) | 1959-09-25 | 1959-09-25 | Preparation of steroids and d-homo-steroids related to oestrone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB975596A true GB975596A (en) | 1964-11-18 |
Family
ID=10415505
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4056060A Expired GB975596A (en) | 1959-09-25 | 1959-09-25 | Preparation of steroids and d-homo-steroids related to oestrone |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB975596A (en) |
-
1959
- 1959-09-25 GB GB4056060A patent/GB975596A/en not_active Expired
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