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
• Article Data: 3

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

Description

(4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one is a complex organic compound characterized by its unique molecular structure, featuring a cyclohexenone ring with a 3,4-dimethoxyphenyl and a 2-propen-1-yl group attached to the 4R position. (4R)-4-(3,4-DiMethoxyphenyl)-4-(2-propen-1-yl)-2-cyclohexen-1-one serves as a crucial intermediate in the synthesis of various pharmaceuticals and natural products.

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

• 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 
• 2859-78-1 4-Bromoveratrole 
• 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

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.