81036-91-1

Basic information

• Product Name: 2-Cyclohexen-1-one, 3-(hydroxyphenylmethyl)-
• CAS NO: 81036-91-1
• Molecular Formula: C13H14O2
• Molecular Weight: 202.253
• Mol File: 81036-91-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2-Cyclohexen-1-one, 3-(hydroxyphenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Cyclohexen-1-one, 3-(hydroxyphenylmethyl)-(81036-91-1)
• EPA Substance Registry System: 2-Cyclohexen-1-one, 3-(hydroxyphenylmethyl)-(81036-91-1)

Safety Data

• Hazardous Substances Data: 81036-91-1(Hazardous Substances Data)

Upstream product

• 81770-76-5 3-bromocyclohexenone 1,2-ethanediyl dithioketal 
• 504-02-9 1,3-cylohexanedione 
• 56671-81-9 3-bromo-2-cyclohexen-1-one 
• 100-52-7 benzaldehyde 
• 930-68-7 cyclohexenone 
• 65825-82-3 3-(Phenylsulfonyl)cyclohex-2-en-1-ol 
• 138832-42-5 (7-Benzenesulfonyl-1,4-dioxa-spiro[4.5]dec-7-yl)-phenyl-methanol 
• 81036-84-2 3-bromocyclohex-2-en-1-one ethylene ketal 
• 75700-18-4 3-<(Methanesulfonyl)oxy>-2-cyclohexenone 
• 56671-82-0 3-Iodocyclohex-2-enone 
• 81770-89-0 7-(α-hydroxybenzyl)-1,4-dithiaspiro<4.5>dec-6-ene 
• 163332-59-0 (3-Methoxy-cyclohex-1-enesulfonyl)-benzene 

Downstream Products

• 58753-28-9 3-benzoylcyclohexan-1-one 
• 100515-02-4 3-benzoylcyclohex-2-en-1-one 

Relevant articles and documents

Synthesis of 3-substituted 2-cyclohexenones through umpoled functionalization

A new protocol to obtain 3-substituted 2-cyclohexenones, was developed by reversing the chemical reactivity of 2-cyclohexenone. One-pot synthesis of 3-substituted 2-cyclohexenones can be achieved by treatment of 3-phenylthiosilyl enol ether with a mixture of t-BuLi/HMPA that allows hydrogen-selective exchange in presence of reactive electrophiles such as aldehydes, ketones and alkyl halides. This affords the corresponding product in moderate overall yield, after silyl enol ether cleavage and concomitant thiophenol elimination initiated with TBAF.

PREPARATION AND REACTIVITY OF FUNCIONALIZED ALKENYL-ZINC, -COPPER, AND -CHROMIUM ORGANOMETALLICS

β-Halogeno-α,β-unsaturated carbonyl derivatives were converted to the corresponding zinc organometallics 2a under mild conditions in THF (Zn dust, 25-45 deg C, 1-4h).These funcionalized alkenylzinc iodides react with a variety of alkenyl and aromatic iodides affording the desired coupling products in 40-97percent yield.The addition of a THF solution of CuCN*2LiCl to 2a affords the corresponding organocopper derivatives 2b which rect with electophiles, such as alkynyl and allylic halides, nitro olefins, enones, and chlorotrimethylstannane providing polyfuncional unsaturated carbonyl compounds in 71-95percent yield.The insertion of chromium (II) chloride to β-iodo and to some β-(p-tosyl)enones in DMF furnishes new funcionalized chromium (III) organometallics 2c which react with aldehydes providing γ-hydroxy unsaturated carbonyl derivatives in 40-91percent yield.The synthetic scope and the limitations of this methodology are discussed. Key words: funcionalized organozinc halides, alkenylchromium(III) compounds, copper-zinc organometallics.

NEW METHODS FOR β-CONJUGATE ADDITION AND β-HYDROXYALKYLATION OF ENONES

β-Conjugate addition and β-hydroxyalkylation of enones have been accomplished by the reaction of ylides, derivated from enones via phosphoniosilylation, with activated olefins and aldehydes in the presence of trimethylsilyl triflate in tetrahydrofuran at