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  • 19-去甲孕酮

    19-Norprogesterone

化合物简介

19-Norprogesterone, also known as 19-norpregn-4-ene-3,20-dione, is a close analogue of the steroid progesterone, lacking only the C-19 methyl group of that molecule. The 1953 discovery that a preparation of 19-norprogesterone gave results equivalent to progesterone in assays detecting inhibitors of ovulation led to the birth of an ultimately successful industrial-academic program of medicinal chemistry-driven research into contraception; when arduous preparation of synthetic 19-norprogesterone was streamlined and crystalline material was obtained, the norsteroid proved 4- to 8-fold more active than the natural steroid. Chemistry used in 1938 to increase the bioavailability of ethisterone was cross-applied by Carl Djerassi and coworkers at Syntex in Mexico City in 1951 to prepare norethisterone, a synthetic norsteroid that was the first orally bioavailable progestin highly active in preventing ovulation. First human trials regarding contraceptive safety and efficacy were conducted using the related noretynodrel from G.D. Searle & Co.

基本信息

CAS:472-54-8
中文别名:19-去甲孕甾-4-烯-3,20-二酮;
英文别名:10-Norprogesterone;17β-Acetylestr-4-en-3-one;(8R,9S,10R,13S,14S,17S)-17-acetyl-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one;19-Norpregn-4-ene-3,20-dione;
分子式:C20H28O2
分子量:300.435
精确质量:300.209
Psa:34.14
Logp:4.3334

编号系统

物化性质

密度:1.1g/cm3
沸点:447.4ºC at 760mmHg
熔点:144-145 °C
闪点:166.8ºC
折射率:1.545
蒸汽压:3.38E-08mmHg at 25°C

安全信息

生产方法及用途

合成路线

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图谱

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