10003-03-9

Basic information

• Product Name: (+/-)-oestrone methyl ester
• CAS NO: 10003-03-9
• Molecular Weight: 284.398
• Mol File: 10003-03-9.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (+/-)-oestrone methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-oestrone methyl ester(10003-03-9)
• EPA Substance Registry System: (+/-)-oestrone methyl ester(10003-03-9)

Safety Data

• Hazardous Substances Data: 10003-03-9(Hazardous Substances Data)

Upstream product

• 1187829-63-5 (+-)-estrone 
• 616-38-6 carbonic acid dimethyl ester 
• 53-16-7 estrone 
• 74-88-4 methyl iodide 
• 35616-23-0 N,N,N,2-tetramethylbenzenaminium iodide 
• 68574-56-1 (1-Methyl-2-oxo-5-vinyl-cyclopentyl)-acetic acid methyl ester 
• 586-37-8 1-(3-Methoxyphenyl)ethanone 
• 818-57-5 Methyl 4-pentenoate 
• 82794-26-1 [(1R,2R)-2-((S)-6-Methoxy-1-methylene-1,2,3,4-tetrahydro-naphthalen-2-yl)-1-methyl-5-methylene-cyclopentyl]-acetaldehyde 
• 83747-48-2 1-(6-Methoxy-3,4-dihydro-naphthalen-1-ylmethyl)-2-methyl-cyclopent-2-enecarboxylic acid methyl ester 
• 83747-50-6 7-Methoxy-4-(2-methyl-1-vinyloxymethyl-cyclopent-2-enylmethyl)-1,2-dihydro-naphthalene 
• 83747-49-3 [1-(6-Methoxy-3,4-dihydro-naphthalen-1-ylmethyl)-2-methyl-cyclopent-2-enyl]-methanol 
• 83747-47-1 4-Bromomethyl-7-methoxy-1,2-dihydro-naphthalene 
• 91044-44-9 (6-Methoxy-3,4-dihydro-naphthalen-1-yl)-methanol 

Downstream Products

• 83782-05-2 (2S,3S)-2-[3-(2-Dimethylaminomethyl-3-methoxy-phenyl)-3-trimethylsilanyl-propyl]-2-methyl-3-vinyl-cyclopentanone 
• 28336-31-4 3-Methoxy-oestratetraen-(1.3.5(10).16) 
• 83782-06-3 {2-Methoxy-6-[3-((1S,5S)-1-methyl-2-oxo-5-vinyl-cyclopentyl)-1-trimethylsilanyl-propyl]-benzyl}-trimethyl-ammonium; iodide 
• 89211-10-9 C₂₆H₃₀O₄S 
• 60727-74-4 2-[3-Methoxy-13-methyl-6,7,8,9,11,12,13,14,15,16-decahydro-cyclopenta[a]phenanthren-(17E)-ylidene]-propionitrile 
• 1229-32-9 (+/-)-3-methoxy-13-methyl-(13r,14c)-11,12,13,14,15,16-hexahydro-cyclopenta[a]phenanthren-17-one 

Relevant articles and documents

A Synthesis of (+/-)-Estrone Methyl Ether via the Tandem Cope-Claisen Rearrangement

A synthesis of (+/-)-estrone methyl ether (7b) is described that employs a new approach to the construction of the estrogen skeleton invoking the tandem Cope-Claisen rearrangement.

Formal total synthesis of (±)-estrone and zirconocene-promoted cyclization of 2-fluoro-1,7-octadienes and ru-catalyzed ring closing metathesis

(Chemical Equation Presented) A new and diastereoselective method for the synthesis of the estrone skeleton from a substituted styrene based on sequential 3-fold use of Cp2ZrBu2 (oxidative addition-alkylation and two cyclization-alkylation sequences) and a ruthenium complex catalyzed RC-metathesis of a sterically hindered diene was developed. The prepared estratetraene was obtained in 7 steps from a commercially available starting material and thus the overall synthesis of estrone could be accomplished in 9 steps. Moreover, we have also found that the course of the reaction of substrates bearing the 2-halo-1,7-diene moiety with Cp2ZrBu 2, i.e., cyclization or oxidative addition to the C-X bond, could be controlled by the nature of the halogen leaving group.

Total synthesis with a chirogenic opening move demonstrated on steroids with estrane or 18a-homoestrane skeleton

A concept of first choice for the synthesis of the title compounds had been proposed by Dane in the late 1930s. It was soon turned down, because the opening move - a chirogenic Diels-Alder reaction - did not work. With Lewis acids as mediators, however, a successful start has been achieved now. With Ti complexes of chelating ligands (Seebach's TADDOLs (= α,α,α',α'-tetraaryl-1,3-dioxolane-4,5-dimethanols)), enantioselective formation of the desired adducts does occur. Efficient total syntheses of 2 and 3a have been accomplished.