125627-55-6

Basic information

• Product Name: (1S,2S,4R)-4-isopropyl-1-methyl-2-phenylselenenylcyclohexan-1-ol
• Synonyms: (1S,2S,4R)-4-isopropyl-1-methyl-2-phenylselenenylcyclohexan-1-ol
• CAS NO: 125627-55-6
• Molecular Weight: 311.326
• Mol File: 125627-55-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (1S,2S,4R)-4-isopropyl-1-methyl-2-phenylselenenylcyclohexan-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,4R)-4-isopropyl-1-methyl-2-phenylselenenylcyclohexan-1-ol(125627-55-6)
• EPA Substance Registry System: (1S,2S,4R)-4-isopropyl-1-methyl-2-phenylselenenylcyclohexan-1-ol(125627-55-6)

Safety Data

• Hazardous Substances Data: 125627-55-6(Hazardous Substances Data)

Upstream product

• 851520-66-6 (+)-dihydrolimonene oxide 
• 1666-13-3 diphenyl diselenide 
• 5707-04-0 Phenylselenyl chloride 
• 1195-31-9 (+)-p-menth-1-ene 
• 203719-54-4 (1RS,2SR,4R)-limonene-1,2-epoxide 
• 5989-27-5 D-limonene 
• 851520-66-6 (3R)-3-isopropyl-6-methyl-7-oxabicyclo[4.1.0]heptane 
• 68395-72-2 N-phenylselenenyl succinimide 
• 112238-64-9 phenylselenyl triflate 

Downstream Products

• 125627-58-9 (1S,2S,4R)-2-Chloro-4-isopropyl-1-methyl-cyclohexanol 
• 25437-28-9 trans-p-menth-1-en-3-ol 
• 34350-53-3 cis-p-menth-1-en-3-ol 
• 117556-62-4 (1S,4S)-4-isopropyl-1-methyl-2-cyclohexen-1-ol 
• 619-62-5 (1R,4S)-4-isopropyl-1-methyl-2-cyclohexen-1-ol 
• 4031-57-6 (1S,2S,4R)-4-isopropyl-1-methylcyclohexane-1,2-diol 
• 5729-92-0 (1S,2R,4R)-4-isopropyl-1-methylcyclohexane-1,2-diol 

Relevant articles and documents

Stereoselective Synthesis of Nonpsychotic Natural Cannabidiol and Its Unnatural/Terpenyl/Tail-Modified Analogues

Here, we report a three-step concise and stereoselective synthesis route to one of the most important phytocannabinoids, namely, (-)-cannabidiol (-CBD), from inexpensive and readily available starting material R-(+)-limonene. The synthesis involved the diastereoselective bifunctionalization of limonene, followed by effective elimination leading to the generation of key chiral p-mentha-2,8-dien-1-ol. The chiral p-mentha-2,8-dien-1-ol on coupling with olivetol under silver catalysis provided regiospecific (-)-CBD, contrary to reported ones which gave a mixture. The newly developed approach was further extended to its structural analogues cannabidiorcin and other tail/terpenyl-modified analogues. Moreover, its opposite isomer (+)-cannabidiol was also successfully synthesized from S-(-)-limonene.

Diastereo and enantioselective synthesis of 1,2-diols promoted by electrophilic selenium reagents

Here we report the first example in which the phenylseleno group is directly substituted by a hydroxy function. The reaction is promoted by the PhSeOSO3H generated "in situ" by oxidation of (PhSe)2 with (NH4)2S2O8 at reflux in a 3:1 mixture of MeCN-H2O. I

TRANS 1,2-FUNCTIONALIZATION OF CYCLOALKENES USING SELENIUM INTERMEDIATES

The reaction of excess phenylselenenyl halides with trisubstituted cyclic olefins in aqueous acetonitrile is regio- and stereospecific and affords trans halohydrins in excellent yields.The reaction proceeds through the formation of a β-hydroxyalkyl phenyl selenide which evolves to halohydrin presumably via an epoxy-intermediate.