17521-83-4

Basic information

• Product Name: 3-methoxygona-1,3,5(10),8,11,13-hexaen-17-one
• CAS NO: 17521-83-4
• Molecular Formula: C₁₈H₁₆O₂
• Molecular Weight: 264.3184
• Mol File: 17521-83-4.mol

Chemical Properties

• Boiling Point: 463.5°C at 760 mmHg
• Flash Point: 217.9°C
• Density: 1.225g/cm³
• Vapor Pressure: 9.03E-09mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: 3-methoxygona-1,3,5(10),8,11,13-hexaen-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxygona-1,3,5(10),8,11,13-hexaen-17-one(17521-83-4)
• EPA Substance Registry System: 3-methoxygona-1,3,5(10),8,11,13-hexaen-17-one(17521-83-4)

Safety Data

• Hazardous Substances Data: 17521-83-4(Hazardous Substances Data)

Upstream product

• 2811-50-9 7-methoxy-4-vinyl-1,2-dihydronaphthalene 
• 71996-27-5 2-(phenylselenenyl)-2-cyclopentenone 
• 115338-42-6 3-methoxy-6,7,16,17-tetrahydro-15H-cyclopenta-phenanthrene 
• 98656-35-0 16,17-dihydro-3-methoxy-15H-cyclopentaphenanthren-17-one 

Downstream Products

• 143216-82-4 3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one methoxime 
• 143216-83-5 3,4,15,16-tetrahydro-trans-3,4-bis<(tert-butyldimethylsilyl)oxy>cyclopentaphenanthren-17-one 
• 143216-84-6 (+/-)-2α-bromo-1,2,3,4,15,16-hexahydro-trans-1β,3α,4β-trihydroxycyclopentaphenanthren-17-one 
• 143216-80-2 15,16-dihydrocyclopentaphenanthren-3,4,17-trione 17-methoxime 
• 143216-81-3 (3S,4S)-3,4-Dihydroxy-3,4,15,16-tetrahydro-cyclopenta[a]phenanthren-17-one O-methyl-oxime 
• 143290-36-2 3,4,15,16-tetrahydro-trans-3,4-dihydroxycyclopentaphenanthren-17-one 
• 143216-79-9 15,16-dihydro-3-hydroxycyclopentaphenanthren-17-one methoxime 
• 24684-50-2 15,16-dihydro-3-hydroxycyclopentaphenanthren-17-one 

Relevant articles and documents

New Synthetic Approaches to Cyclopentaphenanthrenes and Their Carcinogenic Derivatives

A new general synthetic approach to cyclopentaphenanthrenes including their carcinogenic 11-methyl (1b) and 17-keto (2d and 2b) derivatives is reported.The simplest example entails alkylation of the bromomagnesium salt of an enamine derivative of cyclo

A NEW SYNTHESIS OF CYCLOPENTA PHENANTHRENE AND ITS CARCINOGENIC DERIVATIVES

A novel synthesis of ciclopenta phenanthrene and its carcinogenic 11-methyl and 17-keto derivatives is described.

Diels-Alder Reaction of (S)-2-p-Tolylsulfinyl-2-cyclopentenone with Dane's Diene: an Efficient Approach to the Enantioselective Preparation of Perhydro-cyclopentaphenanthrenes

The reactions of (S)-2-p-tolylsulfinyl-2-cylopentenone with Dane's diene catalyzed by EtAlCl2 yields adducts easily desulfinylated into optically pure perhydro-cyclopentaphenanthrenes.The endo-(controlled by CO group) and regio- (controlled by the subs

Synthesis of the Putative Active Metabolites of the Cyclopentaphenanthrenes. Synthesis of the trans-3,4-Dihydro 3,4-Diol and syn-3,4-Diol 1,2-Epoxide Derivatives of the Mutagen 15,16-Dihydrocyclopentaphenanthren-17-one

The first synthesis of the trans-dihydro diol and syn-diol epoxide derivatives of a biologically active cyclopentaphenanthrene is described.The cyclopentaphenanthrene skeleton is rapidly and efficiently assembled utilizing the Lewis acid-catalyzed Diels-Alder reaction of 1,2-dihydro-7-methoxy-4-vinylnaphthalene (5) with an α-heterosubstituted cyclopentenone, a "cyclopentynone" equivalent.It was found that the Diels-Alder reaction of α-(phenylselenenyl)- (6a) or α-bromocyclopentenone (6b) with 5 in the presence of 1.5 equiv of SnCl4 followed by elimination with hydrogen peroxide or DBU produced the key intermediate 15,16-dihydro-3-methoxycyclopentaphenanthren-17-one (10) in 28percent or 59percent overall yield, respectively.The synthesis of the A-ring metabolites features the use of a unique methoxime protecting group for the 17-ketone.The deprotection of the 17-methoxime group of the highly acid-sensitive 3,4-trans-dihydro 3,4-diol bis(TBDMS) ether 15b was achieved through the use of the low-valent titanium reagent produced upon reduction of TiCl3-3THF by DIBAL-H (51percent).Treatment of bis-(TBDMS) ether 16 with TBAF in THF provided the desired 3,4-trans-dihydro 3,4-diol (3) (83percent), thus achieving the synthesis of 3 in 10 steps in 9.6percent overall yield from 6b.In addition, the bay-region syn-3,4-diol 1,2-epoxide (4a) was also synthesized from 3 in two steps in 59percent overall yield.