88847-87-4

Usage

InChI:InChI=1/C18H23ClO2/c1-18-7-6-11-12(14(18)4-5-17(18)21)3-2-10-8-16(20)15(19)9-13(10)11/h8-9,11-12,14,17,20-21H,2-7H2,1H3/t11-,12+,14-,17-,18-/m0/s1

Upstream product

• 50-28-2 estradiol 
• 5707-04-0 Phenylselenyl chloride 
• 50-28-2 estradiol 
• 133586-87-5 2-phenylselenenylestradiol 
• 116382-88-8 2,10β-dichloro-17β-hydroxyestra-1,4-dien-3-one 
• 1743-60-8 17-β-estradiol 17-acetate 
• 116382-89-9 4,10β-dichloro-17β-hydroxyestra-1,4-dien-3-one 
• 1474-52-8 17β-oestradiol diacetate 

Relevant academic research and scientific papers

Effect of 11β-substituents on the regioselective chlorination of estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone

The reaction of 11β-substituted estrogens with 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone affords exclusively ortho-substituted monochlorinated products including a major 4-chloro and a minor 2-chloro derivative.In the absence of an 11β-substituent, regioselectivity is lost, resulting in a mixture of 10β- and ortho-chlorinated products.Keywords: estradiol derivative; regioselective chlorination; 2,3,4,5,6,6-hexachloro-2,4-cyclohexadienone

Reaction of Benzeneselenyl Halides with Estrogens

The reaction of estradiol and estrone with benzeneselenyl chloride affords mainly 2-phenylselenyl adducts which are readily converted into the corresponding 2-halogenated estrogens upon treatment with a variety of reagents.

Efficient regioselective a-ring functionalization of oestrogens

Complete series of 2-halo- and 2-cyano-oestrogens have been prepared in good to high yields: 2-chloro, 2-bromo, 2-iodo, and 2-cyano derivatives via oestrogen-thallium (III) bis(trifluoroacetate) intermediates, and 2- and 4- fluorooestrogens by direct functionalization using N-fluoropyridinium triflate.

10&β-Chloro-17&β-hydroxyestra-1,4-dien-3-one and its Related Compounds

Chlorination of steroidal ring A phenols with N-chloro imide reagents (e.g.N-chlorosuccinimide and trichloroisocyanuric acid) afforded the 10β-chloroestra-1,4-dien-3-one (2) together with a smaller proportion of 2,4,10β-trichloroestra-1,4-dien-3-one (4), 2,10β-, and 4,10β-dichloroestra-1,4-dien-3-one .In contrast with the results of bromination using N-bromo imide reagents, only substitution of aromatic ring A was observed.The structure of compound (2b) was established by an X-ray diffraction study.Compounds (2a) and (2b) were readily reduced to the original phenol, and compound (2a) underwent dienone-phenol rearrangement with acetic anhydride-sulphuric acid to yield 4-chloroestra-1,3,5(10)-triene-1,17-diyl diacetate (7).