5976-62-5

Usage

InChI:InChI=1/C19H24O3/c1-19-10-9-12-11-5-7-16(22-2)18(21)14(11)4-3-13(12)15(19)6-8-17(19)20/h5,7,12-13,15,21H,3-4,6,8-10H2,1-2H3

Upstream product

• 186581-53-3 diazomethane 
• 3131-23-5 4-hydroxyestrone 
• 26624-38-4 3,4-Dimethoxy-1,3,5⁽¹⁰⁾-estratrien-17-one 
• 88016-84-6 4-benzyloxy-3-methoxy-1,3,5⁽¹⁰⁾-estratrien-17-one 
• 1624-62-0 estrone 3-methyl ether 
• 88016-81-3 4-benzyloxy-3-hydroxy-1,3,5⁽¹⁰⁾-estratrien-17-one 
• 85359-09-7 methyl (3-methoxy-17-oxo-1,3,5(10)-estatrien-4-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 85359-02-0 methyl (3-hydroxy-17-oxo-1,3,5(10)-estatrien-4-yl-2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 360771-99-9 3-methoxy-4-hydroxy-17,17-ethylenedioxy-1,3,5⁽¹⁰⁾-estratrien-6-one acetate 
• 360771-98-8 3-methoxy-4-hydroxy-17,17-ethylenedioxy-1,3,5⁽¹⁰⁾-estratrien-6-one 
• 360771-96-6 3,4-dihydroxy-1,3,5⁽¹⁰⁾-estratriene-6,17-dione 
• 360771-97-7 3-methoxy-4-hydroxy-1,3,5⁽¹⁰⁾-estratriene-6,17-dione 
• 14776-82-0 3-methoxy-17,17-ethylenedioxy-1,3,5⁽¹⁰⁾-estratrien-4-ol 
• 85359-10-0 sodium (3-methoxy-17-oxo-1,3,5(10)-estatrien-4-yl-β-D-glucopyranosid)uronate 

Downstream Products

• 26624-38-4 3,4-Dimethoxy-1,3,5⁽¹⁰⁾-estratrien-17-one 
• 85359-18-8 sodium 4-hydroxy-3-methoxy-1,3,5(10)-estatrien-17-one 4-sulfate 

Relevant academic research and scientific papers

Pyridazine N-Oxides as Photoactivatable Surrogates for Reactive Oxygen Species

A method for the photoinduced evolution of atomic oxygen from pyridazine N-oxides was developed. This underexplored oxygen allotrope mediates arene C-H oxidation within complex, polyfunctional molecules. A water-soluble pyridazine N-oxide was also developed and shown to promote photoinduced DNA cleavage in aqueous solution. Taken together, these studies highlight the utility of pyridazine N-oxides as photoactivatable O(3P) precursors for applications in organic synthesis and chemical biology.

Tuning the Reactivity of Peroxo Anhydrides for Aromatic C-H Bond Oxidation

Phenol moieties are key structural motifs in many areas of chemical research from polymers to pharmaceuticals. Herein, we report on the design and use of a structurally demanding cyclic peroxide (spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aromatic substrates. The new peroxide benefits from high thermal stability and can be synthesized from readily available starting materials. The aromatic C-H oxidation using P4 exhibits generally good yields (up to 96%) and appreciable regioselectivities.

Selective synthesis of 4-methoxyestrogen from 4-hydroxyestrogen

The introduction of an oxygen atom into the C-6 position of 4-hydroxyestrogen allowed for the selective methylation of the two phenolic hydroxyl groups. When the 6-oxo derivative of 4-hydroxyestrone was benzylated in ethanol, only the 3-monobenzyl ether was obtained without formation of the 4-monobenzyl ether. Moreover, the 6-carbonyl group was further reduced to methylene almost quantitatively in the reaction of 4-acetoxy-6-oxoestrone 3-benzyl ether derivative with sodium borohydride. Therefore, 4-methoxyestrogen was synthesized by essentially combining these two reactions. Copyright

Methylation of catechol estrogen with diazomethane

Dynamic aspects of methylation of catechol estrogen with diazomethane were investigated by means of thin-layer chromatography. The methylation rate of the hydroxyl group at the C-3 position was almost the same as that of the C-2 hydroxyl group in the reaction of 2-hydroxyestrogen, and 2-3 times that of the C-4 hydroxyl group in the reaction of 4-hydroxyestrogen. In these experiments, the maximum yields of 2-methoxyestrone, 2-hydroxyestrone 3-methyl ether, 4-methoxyesterone and 4-hydroxyesterone 3-methyl ether were 32, 39, 13, and 70%, respectively. In addition, demethylation of catechol estrogen dimethyl ethers with boron tribromide and synthesis of 4-hydroxyestrone monomethyl ethers are described.