68247-73-4

Basic information

• Product Name: 3-methoxy-14,15-methyleneestra-1,3,5-triene-17-ol
• Synonyms: 3-methoxy-14,15-methyleneestra-1,3,5-triene-17-ol;(14R,15α)-3',15-Dihydro-3-methoxycycloprop[14,15]estra-1,3,5(10)-trien-17β-ol;STS-593
• CAS NO: 68247-73-4
• Molecular Formula: C20H26O2
• Molecular Weight: 298.41924
• Mol File: 68247-73-4.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 449.7°Cat760mmHg
• Flash Point: 201.5°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 7.1E-09mmHg at 25°C
• Refractive Index: 1.609
• CAS DataBase Reference: 3-methoxy-14,15-methyleneestra-1,3,5-triene-17-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxy-14,15-methyleneestra-1,3,5-triene-17-ol(68247-73-4)
• EPA Substance Registry System: 3-methoxy-14,15-methyleneestra-1,3,5-triene-17-ol(68247-73-4)

Safety Data

• Hazardous Substances Data: 68247-73-4(Hazardous Substances Data)

Usage

Chemical Class

Estratrienes

Structural Features

Methoxy Group: Attached at the 3-position of the estratriene ring.
Methylene Group: Present at the 14 and 15 positions of the estratriene ring.
Hydroxyl Group: Located at the 17 position of the molecule.

Applications

Medicine and Pharmacology: Potential applications in studying estrogen receptors and hormone replacement therapy.
Selective Estrogen Receptor Modulator (SERM): Investigated for its potential as a SERM.

Research Status

Ongoing investigation for understanding pharmacological properties and potential uses.

Further Research Needed

To comprehensively elucidate its pharmacological properties and applications.

This compound's structure and functional groups make it intriguing for studying hormonal interactions and potential therapeutic applications. Its classification within the estratriene group underscores its relevance in hormone-related research, especially concerning estrogen receptors and related pharmacology.

InChI:InChI=1/C20H26O2/c1-19-8-7-16-15-5-4-14(22-2)9-12(15)3-6-17(16)20(19)11-13(20)10-18(19)21/h4-5,9,13,16-18,21H,3,6-8,10-11H2,1-2H3/t13-,16+,17+,18-,19+,20+/m0/s1

Upstream product

• 73860-50-1 3-Methoxy-14β,15β-methylen-oestra-1,3,5(10)-trien-17-on 
• 156810-19-4 3-methoxy-14α,15α-cyclopropa[a]estra-1,3,5(10),8-tetraen-17-one 
• 156810-18-3 3-methoxy-14α,15α-methylenestra-1,3,5(10),8-tetraen-17α-ol 
• 10003-02-8 14-dehydroestrone 3-methyl ether 
• 35644-58-7 17β-hydroxy-3-methoxy-1,3,5(10),14-estratetraene 
• 74-88-4 methyl iodide 
• 75-11-6 diiodomethane 

Relevant articles and documents

Ionic hydrogenation of 3-methoxy-14α,15α-methylenestra-1,3,5(10),8- tetraen-17α-ol: A correction

3-Methoxy-14α,15α-methylenestra-1,3,5(10,8-etraen-17α-ol on hydrogenation with triethylsilane/trifluoroacetic acid yielded 3-methoxy- 14β,15β-methylenestra-1,3,5(10)-trien-17α-ol, not the 14α,15α-methylene- 9β product as previously described.

Synthesis, Reactivity and 1H-NMR-Spectroscopy of 14,15-Methylene Derivatives of the Androstane and Estratriene Series

Under the activating and syn-directing effect of the 17-hydroxy group the Simmons Smith cyclopropanation of 14,15-unsaturated 17-hydroxy steroids of the androstane and estratriene series 1a, 5 and 9 affords the 14,15-methylene steroids 2a, 6 and 10 with cis position of the 14,15-methylene and 17-hydroxy groups in a stereospecific reaction.Oxidation of these compounds yields the 17-keto derivatives 3, 7 and 11, which were reduced to the compounds 4a, 8 and 12 with trans position of the 14,15-methylene and 17-hydroxy groups by complex hydrides or diborane.In a phase transfer catalyzed reaction dichloro- or dibromocarbene was added to 3β,17β-diacetoxy-5α-androst-14-ene 1b forming the 14β,15β-dihalogenmethylene steroids 13 and 14.The 17-keto steroids 7 and 11 were transformed into 17-methyl and 17-ethynyl derivatives 15-20.Cleavage of the cyclopropane ring of 2a, 2b and 3 by catalytic hydrogenation affords the 14β-methyl derivatives 21-23, the acid catalyzed ring opening with hydrogen chloride yields the 14β-chloro, 15β-methyl derivatives 24-29.Structure elucidation has been established by 1H n.m.r. and mass spectroscopy.The configuration at C17, C14 and C15 was also determined by means of 1H n.m.r. spectroscopy, using the chemical shifts of the 18-protons, the coupling constants and the chemical shifts of the 17-protons.The configuration of the 17-disubstituted steroids was established with the aid of an europium shift reagent.

14,15-Methylene derivatives of the estrane series and methods for preparing same

Compounds of the general formula STR1 in which R' is hydrogen or a methyl radical; R is a hydroxyl, acetoxy, arylaminocarbonyloxy, alkylaminocarbonyloxy radical; Z is hydrogen or a lower alkyl, or R and Z together are oxygen. These compounds exhibit a very favorable separation of desirable contraceptive and undesirable uterine and antigonadotrophic properties.