187850-36-8

Basic information

• Product Name: 2-[3-(3,4-Dimethoxy-phenyl)-4-nitro-4-phenylselanyl-butyl]-5,5-dimethyl-2-vinyl-[1,3]dioxane
• Synonyms: 2-[3-(3,4-Dimethoxy-phenyl)-4-nitro-4-phenylselanyl-butyl]-5,5-dimethyl-2-vinyl-[1,3]dioxane
• CAS NO: 187850-36-8
• Molecular Weight: 534.511
• Mol File: 187850-36-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-[3-(3,4-Dimethoxy-phenyl)-4-nitro-4-phenylselanyl-butyl]-5,5-dimethyl-2-vinyl-[1,3]dioxane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[3-(3,4-Dimethoxy-phenyl)-4-nitro-4-phenylselanyl-butyl]-5,5-dimethyl-2-vinyl-[1,3]dioxane(187850-36-8)
• EPA Substance Registry System: 2-[3-(3,4-Dimethoxy-phenyl)-4-nitro-4-phenylselanyl-butyl]-5,5-dimethyl-2-vinyl-[1,3]dioxane(187850-36-8)

Safety Data

• Hazardous Substances Data: 187850-36-8(Hazardous Substances Data)

Upstream product

• 4230-93-7 3,4-dimethoxynitrostyrene 
• 34837-55-3 Phenylselenyl bromide 
• 187850-35-7 5,5-dimethyl-2-ethenyl-2-(2-iodoethyl)-1,3-dioxane 
• 187850-34-6 2-(2-bromoethyl)-5,5-dimethyl-2-ethenyl-1,3-dioxane 
• 187850-33-5 2,2-bis(2-bromoethyl)-5,5-dimethyl-1,3-dioxane 
• 140200-76-6 α,α'-dibromopentan-3-one 

Downstream Products

• 187850-38-0 (4S,6S)-4-{5-[3,3-(2,2-Dimethylpropylenedioxy)-1-pentenyl]}-4-(3,4-dimethoxyphenyl)-6-{[(1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexyl]oxy}-5,6-dihydro-4H-[1,2]oxazine N-Oxide 
• 187850-39-1 (+)-(5S,6aS,9aR,9bS)-9,9-(2,2-Dimethylpropylenedioxy)-6a-(3,4-dimethoxyphenyl)-5-{[(1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexyl]oxy}hexahydro-1H-isooxazolo-[2,3,3-h] [2,1]benzoxazine 
• 187850-45-9 (+)-(3aS,7aS)-3a-(3,4-dimethoxyphenyl)-1-methyl-6-[(2,2-dimethyl-3-hydroxypropyl)oxy]-7-formyl-2,3,3a,4,5,7a-hexahydro-6H-indole 
• 187850-43-7 (+)-(3aS,7R,7aS)-[3a-(3,4-dimethoxyphenyl)-6,6-(2,2-dimethylpropylenedioxy)-1-methyloctahydroindol-7-yl]methanol 
• 187850-40-4 (+)-[(3aS,7R,7aS)-3a-(3,4-dimethoxyphenyl)-6,6-(2,2-dimethylpropylenedioxy)octahydroindol-7-yl]methanol 
• 468-53-1 (-)-mesembrine 
• 909196-62-9 2-{4-[2-(3,4-Dimethoxyphenyl)-1-nitro-1-butenyl]}-2-ethenyl-5,5-dimethyl-1,3-dioxane 

Relevant articles and documents

Asymmetric construction of a quaternary carbon center by tandem [4 + 2]/[3 + 2] cycloaddition of a nitroalkene. The total synthesis of (-)-mesembrine

An efficient, total synthesis of the Sceletium alkaloid (-)-mesembrine is accomplished in seven steps and 19% yield from a functionalized nitroalkene (itself prepared in six steps and 34% yield from ethyl 3-bromopropionate). The construction of the octahydroindole framework of mesembrine features a tandem inter [4 + 2]/intra [3 + 2] cycloaddition of a 2,2-disubstituted 1-nitroalkene and a chiral vinyl ether derived from (1R,2S)-2-(1-methyl-1-phenylethyl)cyclohexanol as the central strategic element. The two stereogenic centers of the natural product, which include a benzylic, quaternary center, were established in 26/1 selectivity in the tandem process.