BE437740A - - Google Patents

Info

Publication number

BE437740A

BE437740A BE437740DA BE437740A BE 437740 A BE437740 A BE 437740A BE 437740D A BE437740D A BE 437740DA BE 437740 A BE437740 A BE 437740A

Authority

BE

Belgium

Prior art keywords

ether

derivatives

estrone

desc

sodium

Prior art date

Links

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• 150000003839 salts Chemical class 0.000 claims description 4
• 238000000034 method Methods 0.000 claims description 2
• 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
• 238000002360 preparation method Methods 0.000 claims description 2
• OELWYQGRQUQQPD-IOMDMTNGSA-N (+)-(3R)-1-(3,4-dihydroxyphenyl)-7-phenyl-(6E)-6-hepten-3-ol Chemical compound C([C@@H](O)CCC=1C=C(O)C(O)=CC=1)C\C=C\C1=CC=CC=C1 OELWYQGRQUQQPD-IOMDMTNGSA-N 0.000 claims 1
• 239000003599 detergent Substances 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
• 229960003399 estrone Drugs 0.000 description 6
• 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 description 5
• DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 4
• KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
• 125000004432 carbon atom Chemical group C* 0.000 description 3
• DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
• DIQMPQMYFZXDAX-UHFFFAOYSA-N Pentyl formate Chemical compound CCCCCOC=O DIQMPQMYFZXDAX-UHFFFAOYSA-N 0.000 description 2
• RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 2
• MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 2
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
• 229910052799 carbon Inorganic materials 0.000 description 2
• -1 for example Chemical class 0.000 description 2
• 239000000203 mixture Substances 0.000 description 2
• 229910052708 sodium Inorganic materials 0.000 description 2
• 239000011734 sodium Substances 0.000 description 2
• 159000000000 sodium salts Chemical class 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• QGXBDMJGAMFCBF-HLUDHZFRSA-N 5α-Androsterone Chemical compound C1[C@H](O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC[C@H]21 QGXBDMJGAMFCBF-HLUDHZFRSA-N 0.000 description 1
• WKRLQDKEXYKHJB-UHFFFAOYSA-N Equilin Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3=CCC2=C1 WKRLQDKEXYKHJB-UHFFFAOYSA-N 0.000 description 1
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
• QGXBDMJGAMFCBF-UHFFFAOYSA-N Etiocholanolone Natural products C1C(O)CCC2(C)C3CCC(C)(C(CC4)=O)C4C3CCC21 QGXBDMJGAMFCBF-UHFFFAOYSA-N 0.000 description 1
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical group CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical group CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
• HZSIFDFXFAXICF-UHFFFAOYSA-N acetolactone Chemical compound O=C1CO1 HZSIFDFXFAXICF-UHFFFAOYSA-N 0.000 description 1
• 239000002253 acid Substances 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 230000001476 alcoholic effect Effects 0.000 description 1
• 239000003513 alkali Substances 0.000 description 1
• RAJWOBJTTGJROA-RNQTWYFASA-N androstane-3,17-dione Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC21 RAJWOBJTTGJROA-RNQTWYFASA-N 0.000 description 1
• 229940061641 androsterone Drugs 0.000 description 1
• 239000007864 aqueous solution Substances 0.000 description 1
• 230000015572 biosynthetic process Effects 0.000 description 1
• 239000003990 capacitor Substances 0.000 description 1
• 238000006243 chemical reaction Methods 0.000 description 1
• 238000009833 condensation Methods 0.000 description 1
• 230000005494 condensation Effects 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• PDRGHUMCVRDZLQ-UHFFFAOYSA-N d-equilenin Natural products OC1=CC=C2C(CCC3(C4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-UHFFFAOYSA-N 0.000 description 1
• 230000008030 elimination Effects 0.000 description 1
• 238000003379 elimination reaction Methods 0.000 description 1
• PDRGHUMCVRDZLQ-WMZOPIPTSA-N equilenin Chemical compound OC1=CC=C2C(CC[C@]3([C@H]4CCC3=O)C)=C4C=CC2=C1 PDRGHUMCVRDZLQ-WMZOPIPTSA-N 0.000 description 1
• 229940106582 estrogenic substances Drugs 0.000 description 1
• JKKFKPJIXZFSSB-CBZIJGRNSA-N estrone 3-sulfate Chemical compound OS(=O)(=O)OC1=CC=C2[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1 JKKFKPJIXZFSSB-CBZIJGRNSA-N 0.000 description 1
• 229910001385 heavy metal Inorganic materials 0.000 description 1
• 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
• 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
• 239000000543 intermediate Substances 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 125000000468 ketone group Chemical group 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 125000004430 oxygen atom Chemical group O* 0.000 description 1
• 235000011118 potassium hydroxide Nutrition 0.000 description 1
• 229960003387 progesterone Drugs 0.000 description 1
• 239000000186 progesterone Substances 0.000 description 1
• ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
• 239000000243 solution Substances 0.000 description 1
• 239000000126 substance Substances 0.000 description 1
• 238000003786 synthesis reaction Methods 0.000 description 1
• 229960003604 testosterone Drugs 0.000 description 1