156896-96-7

Basic information

• Product Name: γ-Cyano-γ-3,4-dimethoxyphenyl-γ-isopropyl-1-buten
• Synonyms: γ-Cyano-γ-3,4-dimethoxyphenyl-γ-isopropyl-1-buten
• CAS NO: 156896-96-7
• Molecular Weight: 259.348
• Mol File: 156896-96-7.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: γ-Cyano-γ-3,4-dimethoxyphenyl-γ-isopropyl-1-buten(CAS DataBase Reference)
• NIST Chemistry Reference: γ-Cyano-γ-3,4-dimethoxyphenyl-γ-isopropyl-1-buten(156896-96-7)
• EPA Substance Registry System: γ-Cyano-γ-3,4-dimethoxyphenyl-γ-isopropyl-1-buten(156896-96-7)

Safety Data

• Hazardous Substances Data: 156896-96-7(Hazardous Substances Data)

Upstream product

• 583-04-0 vinyl benzoate 
• 20850-49-1 2-(3,4-dimethoxyphenyl)-3-methylbutyronitrile 
• 93-17-4 3,4-dimethoxyphenylacetonitrile 
• 107148-91-4 (2R,3R)-(-)-2-methyl-3-cyano-3-(3,4-dimethoxyphenyl)hex-5-enol 
• 107148-90-3 (2R,3R)-(+)-2-(2-propenyl)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone 
• 107148-88-9 (2R,3R)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone 
• 107148-93-6 (2R,3R)-(-)-1-<(methylsulfonyl)oxy>-2-methyl-3-cyano-3-(3,4-dimethoxyphenyl)hex-5-ene 
• 107148-91-4 (2S,3S)-(+)-2-methyl-3-cyano-3-(3,4-dimethoxyphenyl)hex-5-enol 
• 107148-85-6 (2RS,3S)-2-(3,4-dimethoxyphenyl)-3-methylbutyrolactone 
• 107148-92-5 (2S,3S)-(+)-1-<(methylsulfonyl)oxy>-2-methyl-3-cyano-3-(3,4-dimethoxyphenyl)hex-5-ene 
• 18133-46-5 α-(3,4-dimethoxyphenyl)acetoacetonitrile 
• 2859-78-1 4-Bromoveratrole 
• 1331858-86-6 C₁₇H₂₃NO₄ 
• 107-18-6 allyl alcohol 

Downstream Products

• 115373-89-2 Methanesulfonic acid (S)-4-cyano-4-(3,4-dimethoxy-phenyl)-5-methyl-hexyl ester 
• 107241-84-9 (S)-4-(3,4-Dimethoxy-phenyl)-N¹-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-isopropyl-N¹-methyl-pentane-1,5-diamine 
• 107241-85-0 (R)-4-(3,4-Dimethoxy-phenyl)-N¹-[2-(3,4-dimethoxy-phenyl)-ethyl]-4-isopropyl-N¹-methyl-pentane-1,5-diamine 
• 36622-29-4 (S)-verapamil 
• 107149-06-4 N-<(2R)-2-(3,4-dimethoxyphenyl)-2-isopropyl-5-<(3,4-dimethoxyphenethyl)methylamino>pentyl>-(1S)-10-camphorsulfonamide 
• 107149-06-4 N-<(2S)-2-(3,4-dimethoxyphenyl)-2-isopropyl-5-<(3,4-dimethoxyphenethyl)methylamino>pentyl>-(1S)-10-camphorsulfonamide 
• 115373-89-2 Methanesulfonic acid (R)-4-cyano-4-(3,4-dimethoxy-phenyl)-5-methyl-hexyl ester 
• 36770-70-4 (2R)-(+)-2-(3,4-dimethoxyphenyl)-5-hydroxy-2-isopropylpentanenitrile 
• 36770-70-4 (2S)-(-)-2-(3,4-dimethoxyphenyl)-5-hydroxy-2-isopropylpentanenitrile 

Relevant articles and documents

A Concise and Modular Three-Step Synthesis of (S)-Verapamil using an Enantioselective Rhodium-Catalyzed Allylic Alkylation Reaction

A concise and modular asymmetric synthesis of the calcium channel blocker (S)-verapamil is described. This approach employs an enantioselective rhodium-catalyzed allylic alkylation reaction between an α-isopropyl-substituted benzylic nitrile and allyl benzoate to construct the challenging acyclic quaternary stereocenter. The terminal olefin then serves as a convenient synthetic handle for a hydroamination to introduce the phenethylamine moiety, furnishing (S)-verapamil in three steps and 55% overall yield, thus providing the most efficient synthesis of this important pharmaceutical reported to date. Furthermore, given the modular nature of the synthesis, it can be readily modified to prepare structurally related bioactive agents.

Deacylative allylation: Allylic alkylation via retro-Claisen activation

A new method for allylic alkylation of a variety of relatively nonstabilized carbon nucleophiles is described herein. In this process of "deacylative allylation", the coupling partners, an allylic alcohol and a ketone pronucleophile, undergo in situ retro-Claisen activation to generate an allylic acetate and a carbanion. In the presence of palladium, these reactive intermediates undergo catalytic coupling to form a new C-C bond. In comparison to unimolecular decarboxylative allylation, a commonly utilized method for allylation of carbon anions, deacylative allylation is an intermolecular process. Moreover, deacylative allylation allows the direct coupling of readily available allylic alcohols. Lastly, the full utility of deacylative allylation is demonstrated by the rapid construction of a variety 1,6-heptadienes via 3-component couplings.

Stereospecific synthesis of the enantiomers of verapamil and gallopamil

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