1235-98-9

Usage

Classification

Naturally occurring steroid hormone

Role

Precursor to cortisol and androstenedione

Production sites

Adrenal glands and gonads

Physiological processes involved

Regulation of menstrual cycle
Pregnancy
Development of secondary sexual characteristics

Medical uses

Treatment of congenital adrenal hyperplasia
Support of pregnancy in women at risk of preterm birth

Industrial significance

Important intermediate compound in the synthesis of corticosteroids and sex hormones

Relevance

Significant molecule in endocrinology and steroid chemistry

Upstream product

• 157196-48-0 17β-Hydroxy-17α-(Z-2-tributylstannylvinyl)-4-androsten-3-one 
• 157196-48-0 C₃₃H₅₆O₂Sn 
• 3604-60-2 17alpha-ethynyl-3beta,17beta-dihydroxy-androst-5-ene 
• 434-03-7 levonorgestrel 
• 10291-86-8 17βH-pregna-5,20-diene-3ξ,17-diol 
• 434-03-7 ethisterone 

Relevant academic research and scientific papers

cis-Selective Transfer Semihydrogenation of Alkynes by Merging Visible-Light Catalysis with Cobalt Catalysis

Herein, the first example of visible-light-driven, cobalt-catalyzed transfer semihydrogenation of alkynes to alkenes is reported. It is carried out by using Ir[dF(CF3)ppy]2(dtbbpy)]PF6 as photosensitizer, CoBr2/n-Bu3P as proton-reducing catalyst, and i-Pr2NEt/AcOH as the hydrogen source. Under the established catalytic system, the semihydrogenation proceeds with Z as the major selectivity and with inhibition of over-reduction. Under mild reaction conditions, both internal and terminal alkynes, as well as reducible functional groups such as halogen, cyano, and ester, are tolerated. Preliminary mechanistic studies revealed the dual role of the photosensitizer in initiating the reaction via a single-electron transfer process and controlling the stereoselectivity via an energy transfer process. (Figure presented.).

Method for catalytically reducing alkynes into olefins through visible light induction

The invention discloses a method for catalytically reducing alkynes into olefins through visible light induction. The method can avoid generation of over-reduced alkane products and the highest yieldis 99%. The method comprises the following steps: by taking an alkyne as a raw material, adding a photosensitizer and a cobalt catalyst, then adding a phosphine ligand or bipyridine ligand, an electronic sacrificial reagent, acetic acid and an organic solvent under inert gas protection, and irradiating with blue light at room temperature for 7-14 hours; and after the reaction is finished, spin-drying an obtained reaction solution, and carrying out silica gel column chromatography separation to obtain an olefin product; wherein the organic solvent is 1, 4-dioxane or tetrahydrofuran, and the alkyne is an aliphatic alkyne or an aromatic alkyne. Reduction of alkyne is realized through a hydrogen transfer strategy, use of dangerous hydrogen is avoided, generation of overreduction products is avoided, reaction conditions are mild, the reaction yield is high, and the method has a good application prospect.

Novel steroidal antiestrogens and antiandrogens and uses thereof

The present invention comprises the design, synthesis and development of a new class of chemotherapeutic agents for prophylactic and therapeutic treatments in a mammal, particularly a human, believed to be at risk of suffering from a hormone-responsive di

STEROID SPIROLACTONIZATION

A steroid comprising a 17-spirolactone or corresponding open lactone structure is obtained by carbonylation of a 17-alkenyl or 17-alkynyl substrate. A 17-alkenyl intermediate may be prepared by semi-hydrogenation of a 17-alkynyl group. Multiple reaction schemes are disclosed for preparation of a 3-keto-9,11-epoxy-17-spirolactone steroid such as eplerenone. Novel intermediates are also disclosed, as well as steps for forming such novel intermediates, or converting them to further intermediates or products, by semi-hydrogenation, carbonylation, 6,7-dehydrogenation, furylation or other transformations or combinations thereof.

Preparation of 17α-iodoethynylandrosta- And 17α-(2-iodoethenyl) androsta-4,6-dien-17β-ol-3-ones as active site-directed photoaffinity ligands for androgen-binding proteins

Unsaturated analogues of androst-4-en-17β-ol-3-one, each with a 17α-iodoethynyl or 17α-(2-iodoethenyl) substituent, were prepared, and their relative binding affinities (RB As) for androgen-binding protein (ABP) were compared with those of 5α-androstan-17β-ol-3-one, androst-4-en-17β-ol-3-one, androsta-4, 6-dien-17β-ol-3-one, and androsta-1,4,6-trien-17β-ol-3-one. These binding studies indicate that the iodine[125I] analogues of 17α-iodoethynyl and 17α-[(E)-2-iodoethenyl] derivatives of androsta-4,6-dien-17β-ol-3-one and androsta-1,4,6-trien-17β-ol-3-one will have RBAs at least twice as great as that of 5α-androstan-17β-ol-3-one. They can be prepared from 17α-ethynylandrosta-4-en-17β-ol-3-one, the final synthetic step using N-[125I]iodosuccinimide, and are potential radioiodinated, active site-directed photoaffinity ligands for ABP and testosterone-binding globulin.