13669-35-7

Basic information

• Product Name: Pyridine, 4-cyclohexyl-
• CAS NO: 13669-35-7
• Molecular Formula: C11H15N
• Molecular Weight: 161.247
• Mol File: 13669-35-7.mol
• Article Data: 27

Chemical Properties

• CAS DataBase Reference: Pyridine, 4-cyclohexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 4-cyclohexyl-(13669-35-7)
• EPA Substance Registry System: Pyridine, 4-cyclohexyl-(13669-35-7)

Safety Data

• Hazardous Substances Data: 13669-35-7(Hazardous Substances Data)

Upstream product

• 91-22-5 quinoline 
• 110-82-7 cyclohexane 
• 1122-54-9 methyl (4-pyridyl) ketone 
• 98-89-5 Cyclohexanecarboxylic acid 
• 91-19-0 2,3-diethynylquinoxaline 
• 201230-82-2 carbon monoxide 
• 181219-01-2 4-pyridineboronic acid pinacol ester 
• 1692-15-5 4-pyridylboronic acid 
• 94356-63-5 4-cyclohex-1-enyl-pyridine 
• 110-86-1 pyridine 
• 126812-30-4 1,3-dioxoisoindolin-2-yl cyclohexanecarboxylate 
• 446065-11-8 cyclohexyltrifluoro-λ⁴-borane potassium salt 
• 59137-44-9 3-carboxy-2-(pyridin-1-ium-1-yl)propanoate 
• 45458-31-9 N-Aminopyridinium 

Downstream Products

• 1012886-77-9 4-cyclohexyl-1-(2-phenyl-allyl)pyridinium bromide 
• 60601-62-9 4-cyclohexenylpiperidine hydrochloride 

Relevant articles and documents

Studies on tertiary amine oxides. LXXXII. The reaction of 1-oxido-4(or 2)-pyridinediazonium tetrafluoroborate with olefins in the presence of palladium complex

-

Practical and Regioselective Synthesis of C-4-Alkylated Pyridines

The direct position-selective C-4 alkylation of pyridines has been a long-standing challenge in heterocyclic chemistry, particularly from pyridine itself. Historically this has been addressed using prefunctionalized materials to avoid overalkylation and mixtures of regioisomers. This study reports the invention of a simple maleate-derived blocking group for pyridines that enables exquisite control for Minisci-type decarboxylative alkylation at C-4 that allows for inexpensive access to these valuable building blocks. The method is employed on a variety of different pyridines and carboxylic acid alkyl donors, is operationally simple and scalable, and is applied to access known structures in a rapid and inexpensive fashion. Finally, this work points to an interesting strategic departure for the use of Minisci chemistry at the earliest possible stage (native pyridine) rather than current dogma that almost exclusively employs Minisci chemistry as a late-stage functionalization technique.

Visible-Light-Driven C4-Selective Alkylation of Pyridinium Derivatives with Alkyl Bromides

Reported herein is a general strategy for the photochemical cross-coupling between N-amidopyridinium salts and various alkyl bromides under photocatalyst-free conditions, granting facile access to various C4-alkylated pyridines. This approach exploits the intriguing photochemical activity of electron donor-acceptor (EDA) complexes between N-amidopyridinium salts and bromide, which provides a photoactive handle capable of generating silyl radicals and driving the alkylation process. The robustness of this protocol was further demonstrated by the late-stage functionalization of complex compounds under mild and metal-free conditions.

Efficient Diastereoselective Three-Component Synthesis of Pipecolic Amides

An efficient Ugi-type three-component reaction (U-3CR) for the synthesis of pipecolic amides is reported. The U-3CR between electronically diverse isocyanides, carboxylic acids and 4-substituted Δ1-piperideines proceeds in a highly diastereoselective fashion. The Δ1-piperideines are obtained by NCS-mediated oxidation of the corresponding 4-substituted piperidines, which in turn are generated by an efficient two-step procedure involving the alkylation of 4-picoline and subsequent catalytic hydrogenation of the pyridine ring. We demonstrate the utility of this U-3CR, in combination with the convertible isocyanide 2-bromo-6-isocyanopyridine, in the synthesis of the anticoagulant argatroban.