450406-20-9

Basic information

• Product Name: 3-hydroxy-3-methylcyclohex-1-ene-1-carbonitrile
• Synonyms: 3-hydroxy-3-methylcyclohex-1-ene-1-carbonitrile
• CAS NO: 450406-20-9
• Molecular Weight: 137.181
• Mol File: 450406-20-9.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-hydroxy-3-methylcyclohex-1-ene-1-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-3-methylcyclohex-1-ene-1-carbonitrile(450406-20-9)
• EPA Substance Registry System: 3-hydroxy-3-methylcyclohex-1-ene-1-carbonitrile(450406-20-9)

Safety Data

• Hazardous Substances Data: 450406-20-9(Hazardous Substances Data)

Upstream product

• 60274-60-4 1-chloro-5-iodopentane 
• 25017-78-1 3-cyano-2-cyclohexenone 
• 676-58-4 methylmagnesium chloride 
• 615265-46-8 1-(1,1-dimethyl-1-silaethoxy)-3-methylcyclohex-2-ene-1-carbonitrile 
• 1193-18-6 3-methylcyclohexen-2-one 
• 615265-49-1 3-methyl-3-methylsulfanylmethoxy-cyclohex-1-enecarbonitrile 

Downstream Products

• 450406-25-4 (1SR,5RS,6SR)-5-hydroxy-5-methyl-7-methylidenebicyclo[4.3.0]nonane-1-carbonitrile 

Relevant articles and documents

Metalated nitriles: stereodivergent cation-controlled cyclizations

Stereodivergent cyclizations of γ-hydroxy cyclohexanecarbonitriles are controlled simply through judicious choice of cation in the alkylmetal base. Deprotonating a series of cyclic γ-hydroxy nitriles with i-PrMgBr generates C-magnesiated nitriles that cyclize under stereoelectronic control to cis-fused hydrindanes, decalins, and bicyclo[5.4.0]undecanes. An analogous deprotonation with BuLi triggers cyclization to trans-fused hydrindanes, decalins, and bicyclo[5.4.0]undecanes consistent with a sterically controlled electrophilic attack on an equatorial nitrile anion. Using cations to control the geometry of metalated nitriles provides a versatile, stereodivergent cyclization to cis- and trans-hydrindanes, decalins, and [5.4.0]undecanes, and reveals the key geometric requirements for intramolecular SN2 and SN2′ displacements.