33357-38-9

Basic information

• Product Name: Quinoline, 4-cyclohexyl-
• CAS NO: 33357-38-9
• Molecular Formula: C15H17N
• Molecular Weight: 211.307
• Mol File: 33357-38-9.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: Quinoline, 4-cyclohexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Quinoline, 4-cyclohexyl-(33357-38-9)
• EPA Substance Registry System: Quinoline, 4-cyclohexyl-(33357-38-9)

Safety Data

• Hazardous Substances Data: 33357-38-9(Hazardous Substances Data)

Upstream product

• 91-22-5 quinoline 
• 108-85-0 1-bromocyclohexane 
• 110-82-7 cyclohexane 
• 626-62-0 Cyclohexyl iodide 
• 41320-40-5 <<(methylthio)thiocarbonyl>oxy>cyclohexane 
• 98-89-5 Cyclohexanecarboxylic acid 
• 1613-37-2 Quinoline N-oxide 
• 51342-20-2 N-methoxyquinolinium methosulfate 
• 611-35-8 4-chloroquinoline 
• 931-51-1 cyclohexylmagnesiumchloride 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 1035458-54-8 4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)quinoline 
• 2177-34-6 1-cyclohexylprop-2-en-1-one 
• 1384467-06-4 C₂₀H₂₉NO₃ 

Relevant articles and documents

Rearomatization of trifluoromethyl sulfonyl dihydropyridines: Thermolysis vs photolysis

In this article, we describe the static gas-phase pyrolysis, microwave-induced pyrolysis, and photolysis reactions of trifluoromethyl sulfonyl dihydropyridines. The goal of this work was to find a methodology that allows obtaining of substituted pyridines-which are known to be difficult to synthesize-to be reused in a new substitution reaction. We demonstrated that it is possible to achieve the rearomatization process by the elimination of the trifluoromethyl sulfonyl moiety through the 3 processes, with the static pyrolysis being the best method to obtain the substituted pyridines. In addition, we propose the 1,4-elimination (CF3SO2 + H) as the first step, since it is the less energetic process, as has also been corroborated by calculations. A competitive reaction (CO2 extrusion) also occurs, yielding undesired products. Copyright

Dearomative Photocatalytic Construction of Bridged 1,3-Diazepanes

The construction of diverse sp3-rich skeletal ring systems is of importance to drug discovery programmes and natural product synthesis. Herein, we report the photocatalytic construction of 2,7-diazabicyclo[3.2.1]octanes (bridged 1,3-diazepanes) via a reductive diversion of the Minisci reaction. The fused tricyclic product is proposed to form via radical addition to the C4 position of 4-substituted quinoline substrates, with subsequent Hantzsch ester-promoted reduction to a dihydropyridine intermediate which undergoes in situ two-electron ring closure to form the bridged diazepane architecture. A wide scope of N-arylimine and quinoline derivatives was demonstrated and good efficiency was observed in the construction of sterically congested all-carbon quaternary centers. Computational and experimental mechanistic studies provided insights into the reaction mechanism and observed regioselectivity/diastereoselectivity.

Visible-Light-Initiated Manganese Catalysis for C?H Alkylation of Heteroarenes: Applications and Mechanistic Studies

A visible-light-driven Minisci protocol that employs an inexpensive earth-abundant metal catalyst, decacarbonyldimanganese Mn2(CO)10, to generate alkyl radicals from alkyl iodides has been developed. This Minisci protocol is compatible with a wide array of sensitive functional groups, including oxetanes, sugar moieties, azetidines, tert-butyl carbamates (Boc-group), cyclobutanes, and spirocycles. The robustness of this protocol is demonstrated on the late-stage functionalization of complex nitrogen-containing drugs. Photophysical and DFT studies indicate a light-initiated chain reaction mechanism propagated by .Mn(CO)5. The rate-limiting step is the iodine abstraction from an alkyl iodide by .Mn(CO)5.