14003-77-1

Basic information

• Product Name: Phenol, 2-(2-cyclohexen-1-yl)-
• CAS NO: 14003-77-1
• Molecular Formula: C12H14O
• Molecular Weight: 174.243
• Mol File: 14003-77-1.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Phenol, 2-(2-cyclohexen-1-yl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 2-(2-cyclohexen-1-yl)-(14003-77-1)
• EPA Substance Registry System: Phenol, 2-(2-cyclohexen-1-yl)-(14003-77-1)

Safety Data

• Hazardous Substances Data: 14003-77-1(Hazardous Substances Data)

Upstream product

• 822-67-3 Cyclohex-2-enol 
• 108-95-2 phenol 
• 1165952-91-9 cyclohexa-1,3-diene 
• 1521-51-3 rac-3-bromocyclohexene 
• 76644-52-5 rac-3-acetoxycyclohexene 
• 7429-37-0 trans-1,2-dibromocyclohexane 
• 139-02-6 sodium phenoxide 
• 5614-35-7 3-phenoxycyclohexene 

Downstream Products

• 13524-79-3 1,2,3,4,4a,9b-hexahydrodibenzo[b,d]furan 
• 13130-19-3 1,2,3,4-tetrahydrodibenzo[b,d]furan 
• 56821-94-4 (4aS,9bS)-1,2,4a,9b-Tetrahydro-dibenzofuran 
• 13524-72-6 1-(2-hydroxyphenyl)cyclohexene 
• 27124-70-5 1-(cyclohex-2-enyl)-2-methoxybenzene 
• 59457-19-1 (2-cyclohex-2-enyl-phenoxy)-acetic acid 

Relevant articles and documents

Gold catalysis: Experimental mechanistic insights into the anellation of phenols with 1,3-dienes Dedicated to Prof. Hubert Schmidbaur on the occasion of his 80th birthday.

An intermediate of the anellation reaction of phenols and 1,3-dienes could be detected, isolated and characterized as the hydroarylation product. The other conceivable intermediate, the hydroaryloxylation product, was prepared via Pd-catalysis and converted under the conditions of the gold catalysis, too. Under exactly the same conditions a very fast Claisen rearrangement took place delivering the formal hydroarylation product as well. After this fast intermolecular formation of the intermediate (formed either directly via the hydroarylation pathway or via a hydroaryloxylation/Claisen rearrangement sequence) the subsequent intramolecular reaction leading to the product turned out to be significantly slower. The major product is the cis-diastereomer (cis-3/trans-3 = 12:1).

Calcium-catalyzed friedel-crafts alkylation at room temperature

Chemical Equatation Representation A novel calcium catalyst was found to efficiently functionalize electron-rich arenes with secondary and tertiary benzylic, propargylic, and allylic alcohols under very mild reaction conditions. The new catalyst system significantly enlarges the scope of the reaction, which was previously limited except for the few examples with secondary benzylic alcohols.

Photogeneration of o-Quinone Methides from o-Cycloalkenylphenols

6-Alkylidenecyclohexa-2,4-dienones (o-quinone methides II) have been generated by photolysis of 2-(2′-cycloalkenyl)phenols 1 and trapped by methanol to give the ring-opened products 2. The best results have been obtained with the cyclohexenyl derivatives 1a, 1e, and 1f. In the case of the cyclopentenyl derivative 1b, photoproduct 2b was not observed, whereas only small amounts of 2c and 2d were formed from the seven- and eight-membered ring analogues 1c and 1d. Thus, ring size appears to be a key factor in the formation of o-quinone methides. This experimental result has been rationalized by means of density-functional theory (DFT) calculations. On the other hand, phenol substitution also appears to play a role in the process. Thus, electron-withdrawing groups such as CF3 (1f) accelerate the reaction, whereas the opposite is true for electron-donating groups such as OCH 3 (1e). This is explained by an excited-state intramolecular proton transfer (ESIPT) mechanism, as the above results are consistent with the excited-state acidities of the different phenols. The lack of reactivity in the case of ketone 1g, where the intersystem crossing quantum yield is close to unity, allows us to rule out a mechanism involving the triplet state.