866394-49-2

Basic information

• Product Name: (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one
• Synonyms: (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one
• CAS NO: 866394-49-2
• Molecular Formula: C₁₇H₂₀O₃
• Molecular Weight: 272.3389
• Product Categories: Aromatics, Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 866394-49-2.mol

Chemical Properties

• Appearance: /
• Solubility: Chloroform, Ethyl Acetate
• CAS DataBase Reference: (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one(866394-49-2)
• EPA Substance Registry System: (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one(866394-49-2)

Safety Data

• Hazardous Substances Data: 866394-49-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one is used as an intermediate in the synthesis of Mesembrine (M338950), a serotonin-uptake inhibitor. Mesembrine occurs naturally as the (-)-form and has potential applications in the treatment of neurological disorders and mood regulation due to its ability to modulate serotonin levels in the brain.
Used in Natural Product Synthesis:
(4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one is also utilized in the synthesis of other natural products that possess biological activities. Its unique structure allows for the development of novel compounds with potential therapeutic benefits, contributing to the advancement of drug discovery and the exploration of natural resources for medicinal purposes.

Upstream product

• 2859-78-1 4-Bromoveratrole 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 504-02-9 1,3-cylohexanedione 
• 70779-49-6 4,4-ethylenedioxy-1-(3',4'-dimethoxyphenyl)cyclohexene 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 866394-48-1 (7R,8S)-8-Allyl-8-(3,4-dimethoxy-phenyl)-1,4-dioxa-spiro[4.5]decan-7-ol 

Downstream Products

• 468-53-1 (-)-mesembrine 
• 71294-61-6 (R)-4-(3,4-Dimethoxy-phenyl)-4-(2-methylamino-ethyl)-cyclohex-2-enol 
• 866394-50-5 Toluene-4-sulfonic acid 2-[(R)-1-(3,4-dimethoxy-phenyl)-4-hydroxy-cyclohex-2-enyl]-ethyl ester 
• 321351-51-3 (4R)-4-(3,4-dimethoxyphenyl)-4-(2-hydroxyethyl)cyclohex-2-enole 

Relevant articles and documents

Diastereoselective construction of quaternary carbons directed via macrocyclic ring conformation: Formal synthesis of (-)-mesembrine

(Chemical Equation Presented) In this article, we report a highly diastereoselective new method for the generation of quaternary carbon centers through an anionic oxy-Cope/alkylation sequence where the diastereoselectivity is induced by the conformation o

Palladium-catalyzed asymmetric direct intermolecular allylation of α-aryl cyclic vinylogous esters: Divergent synthesis of (+)-oxomaritidine and (?)-mesembrine

We demonstrate that α-aryl cyclic vinylogous esters are competent substrates in the direct intermolecular Pd-catalyzed asymmetric allylic alkylation, enabling a straightforward enantioselective synthesis of 6-allyl-6-aryl-3-ethoxycyclohex-2-en-1-ones, common motifs embedded in numerous structurally diverse natural products. As an initial demonstration of the utility of this protocol, the first catalytic enantioselective total synthesis of (+)-oxomaritidine and an improved five-step catalytic enantioselective synthesis of (?)-mesembrine have been completed divergently.

Opening of aryl-substituted epoxides to form quaternary stereogenic centers: Synthesis of (-)-mesembrine

Cycloalkanones are easily converted into aryl-substituted cyclic alkenes by the addition of an aryl Grignard reagent followed by dehydration. These alkenes are good substrates for asymmetric epoxidation. We have found that the addition of allylic and benzylic Grignard reagents can occur preferentially at the benzylic position of the derived epoxides to give the quaternary stereogenic center. This approach led to a short synthesis of the nanomolar serotonin re-uptake inhibitor (-)-mesembrine.