139765-96-1

Basic information

• Product Name: Isoquinoline, 3-cyclohexyl-
• CAS NO: 139765-96-1
• Molecular Formula: C15H17N
• Molecular Weight: 211.307
• Mol File: 139765-96-1.mol

Chemical Properties

• CAS DataBase Reference: Isoquinoline, 3-cyclohexyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Isoquinoline, 3-cyclohexyl-(139765-96-1)
• EPA Substance Registry System: Isoquinoline, 3-cyclohexyl-(139765-96-1)

Safety Data

• Hazardous Substances Data: 139765-96-1(Hazardous Substances Data)

Upstream product

• 119-65-3 isoquinoline 
• 446065-11-8 cyclohexyltrifluoro-λ⁴-borane potassium salt 
• 931-48-6 2-cyclohexylacetylene 
• 6630-33-7 ortho-bromobenzaldehyde 
• 396717-17-2 2-(2-cyclohexylethynyl)benzaldehyde 
• 41320-40-5 <<(methylthio)thiocarbonyl>oxy>cyclohexane 

Relevant articles and documents

Synthesis of isoquinolines and naphthyridines by electrophilic ring closure of iminoalkynes.

Substituted isoquinolines and naphthyridines have been prepared in good to excellent yields by the reaction of iminoalkynes with a variety of electrophiles under mild reaction conditions. Reaction: see text.

Synthesis of isoquinolines and pyridines by the palladium- and copper-catalyzed coupling and cyclization of terminal acetylenes

(Matrix presented) 3-Substituted isoquinolines have been synthesized by the coupling of aryl- and alkenyl-substituted terminal acetylenes with the tert-butylimine of o-iodobenzaldehyde in the presence of a palladium catalyst. Alkyl-substituted acetylenes

Development of a Quinolinium/Cobaloxime Dual Photocatalytic System for Oxidative C-C Cross-Couplings via H2Release

Designing molecular photocatalysts for potent photochemical reactivities ranks among the most challenging but rewarding endeavors in synthetic photochemistry. Herein, we document a quinoline-based organophotoredox catalyst, 2,4-bis(4-methoxyphenyl)quinoli

A room-temperature protocol to access isoquinolines through Ag(i) catalysed annulation of o-(1-alkynyl)arylaldehydes and ketones with NH4OAc: Elaboration to berberine and palmatine

An efficient and mild protocol for the direct construction of aryl- and alkyl-substituted isoquinolines has been realized through silver nitrate catalyzed aromatic annulation of o-(1-alkynyl)arylaldehydes and ketones with ammonium acetate. The salient feature of this methodology is that this annulation could be effected at room temperature leading to a wide range of isoquinoline derivatives in good to excellent yields. Additionally, this approach has been employed to the synthesis of biologically important isoquinoline alkaloids such as berberine and palmatine.

Facile synthesis of 3-substituted isoquinolines derivatives via microwave-assisted tandem three-component coupling cyclization

A novel three-component reaction of o-bromobenzaldehyde, terminal alkynes and tert-butyl amine has been established, which proceeded smoothly to give 3-substituted isoquinolines in good yields in the presence of palladium/copper catalysts under microwave irradiation.

Synthesis of isoquinolines and pyridines by the palladium/copper-catalyzed coupling and cyclization of terminal acetylenes and unsaturated imines: The total synthesis of decumbenine B

Monosubstituted isoquinolines and pyridines have been prepared in good to excellent yields via coupling of terminal acetylenes with the tert-butylimines of o-iodobenzaldehydes and 3-halo-2-alkenals in the presence of a palladium catalyst and subsequent copper-catalyzed cyclization of the intermediate iminoalkynes. In addition, isoquinoline heterocycles have been prepared in excellent yields via copper-catalyzed cyclization of iminoalkynes. The choice of cyclization conditions is dependent upon the nature of the terminal acetylene that is employed, as only aryl and alkenyl acetylenes cyclize under the palladium-catalyzed reaction conditions that have been developed. However, aryl-, vinylic-, and alkyl-substituted acetylenes undergo palladium-catalyzed coupling and subsequent copper-catalyzed cyclization in excellent yields. The total synthesis of the isoquinoline natural product decumbenine B has been accomplished in seven steps and 20% overall yield by employing this palladium-catalyzed coupling and cyclization methodology.

Synthesis of substituted isoquinolines by electrophilic cyclization of iminoalkynes

The tert-butylimines of o-(1-alkynyl)benzaldehydes and analogous pyridinecarbaldehydes have been cyclized under very mild reaction conditions in the presence of I2, ICl, PhSeCl, PhSCl, and p-O2-NC6H4SCl to give the corresponding halogen-, selenium-, and sulfur-containing disubstituted isoquinolines and naphthyridines, respectively. This methodology accommodates a variety of iminoalkynes and affords the anticipated heterocycles in moderate to excellent yields. Monosubstituted isoquinolines and naphthyridines have been synthesized by the metal-catalyzed ring closure of these same iminoalkynes. The silver-catalyzed ring closure is highly effective in cyclizing aryl-, alkenyl-, and alkyl-substituted iminoalkynes at 50°C.

A novel radical reaction of alkyl xantates useful for the selective substitution of heteroaromatic bases

Cyclohexyl radical is generated from cyclohexyldithiocarbonate and benzoyl peroxide. The radical source is used for the alkylation of heteroaromatic bases.