866394-48-1

Basic information

• Product Name: (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol
• Synonyms: (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol
• CAS NO: 866394-48-1
• Molecular Formula: C₁₉H₂₆O₅
• Molecular Weight: 334.40674
• Product Categories: Aromatics, Chiral Reagents, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 866394-48-1.mol

Chemical Properties

• Boiling Point: 477.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Solubility: Chloroform, Ethyl Acetate
• PKA: 14.89±0.40(Predicted)
• CAS DataBase Reference: (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol(866394-48-1)
• EPA Substance Registry System: (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol(866394-48-1)

Safety Data

• Hazardous Substances Data: 866394-48-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol is used as an intermediate in the synthesis of Mesembrine (M338950) for its serotonin-uptake inhibitory properties. This makes it a valuable compound in the development of potential antidepressant and anxiolytic medications, as it can help regulate mood and alleviate symptoms of depression and anxiety.
Used in Research and Development:
As a key intermediate in the synthesis of Mesembrine, (7R,8S)-8-(3,4-DiMethoxyphenyl)-8-(2-propen-1-yl)-1,4-dioxaspiro[4.5]decan-7-ol plays a crucial role in research and development efforts aimed at understanding the mechanisms of action and potential therapeutic applications of Mesembrine. This can lead to the discovery of new drugs and treatments for various mental health disorders.

Upstream product

• 2622-05-1 allylmagnesium bromide 
• 70779-49-6 4,4-ethylenedioxy-1-(3',4'-dimethoxyphenyl)cyclohexene 
• 4746-97-8 cyclohexanedione monoethylene ketal 
• 2859-78-1 4-Bromoveratrole 

Downstream Products

• 321351-51-3 (4R)-4-(3,4-dimethoxyphenyl)-4-(2-hydroxyethyl)cyclohex-2-enole 
• 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 
• 866394-49-2 (R)-1-allyl-3',4'-dimethoxy-2,3-dihydro-[1,1'-biphenyl]-4(1H)-one 

Relevant articles and documents

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.