123355-84-0

Basic information

• Product Name: (R)-1-(3',4'-dimethoxyphenethyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• Synonyms: (R)-1-(3',4'-dimethoxyphenethyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
• CAS NO: 123355-84-0
• Molecular Weight: 371.477
• Mol File: 123355-84-0.mol
• Article Data: 15

Chemical Properties

• CAS DataBase Reference: (R)-1-(3',4'-dimethoxyphenethyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-(3',4'-dimethoxyphenethyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(123355-84-0)
• EPA Substance Registry System: (R)-1-(3',4'-dimethoxyphenethyl)-2-methyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline(123355-84-0)

Safety Data

• Hazardous Substances Data: 123355-84-0(Hazardous Substances Data)

Upstream product

• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 97243-37-3 3-(3',4'-dimethoxyphenyl)-2,3-dibromopropanoic acid 
• 69731-27-7 1-bromo-2-(3',4'-dimethoxyphenyl)ethene 
• 4302-52-7 4-ethynylveratrole 
• 2316-26-9 3,4-dimethoxycinnamic acid 
• 1374870-00-4 6,7-dimethoxy-1-(3,4-dimethoxyphenylethynyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline 
• 111427-24-8 N-<3-(3,4-dimethoxyphenyl)propionyl>-2-thiazolidine-2-thione 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 2107-70-2 3,4-methoxycinnamic acid 
• 20944-14-3 1-[2-(3,4-dimethoxyphenyl)-ethyl]-6,7-dimethoxy-3,4-dihydroisoquinoline 
• 20944-13-2 N-<2-(3,4-dimethoxyphenyl)ethyl>-3-(3,4-dimethoxyphenyl)propionamide 
• 51842-87-6 3-(3,4-dimethoxy-phenyl)-propionyl chloride 
• 20226-10-2 1-<2-(3,4-dimethoxyphenyl)ethyl>-3,4-dihydro-6,7-dimethoxy-2-methylisoquinolinium iodide 
• 186581-53-3 diazomethane 

Downstream Products

• 105578-49-2 (+/-)-N,N-Dimethyl-6,7,3',4'-tetramethoxyphenylethyl-1,2,3,4-tetrahydroisoquinolinium iodide 
• 97117-83-4 3-(3,4-Dimethoxy-phenyl)-1-<4,5-dimethoxy-2-<2-(methyl-aethoxycarbonyl-amino)-aethyl>-phenyl>-propen-(1) 

Relevant articles and documents

Succinct Syntheses of Methopholine, (±)-Homolaudanosine, and (±)-Dysoxyline via Metal-free One-Pot Double Alkylation on 1-Methyl-3,4-dihydroisoquinolines

A mild one-pot and metal-free condition was discovered to implement two different alkyl groups chemoselectively on 1-methyl-3,4-dihydroisoquinoline (1-Me-DHIQ), one at the nitrogen another at the C1-methyl group. This chemistry is compatible with various DHIQs as well as alkyl halides. Application of this chemistry facilitated the concise syntheses of methopholine, (±)-homolaudanosine, and (±)-dysoxyline, requiring only two steps from 6,7-dimethoxy-1-Me-DHIQ.

Biomimetic Total Synthesis of Dysoxylum Alkaloids

A five-step total synthesis of Dysoxylum alkaloids has been achieved using a biomimetic approach from zanthoxylamide protoalkaloids. The synthesis featured a direct amidation and a Bischler-Napieralski reaction to form the dihydroisoquinoline ring, which

Practical metal-free C(sp3)-H functionalization: Construction of structurally diverse α-substituted N-benzyl and N-allyl carbamates

Described is a practical and universal C-H functionalization of readily removable N-benzyl and N-allyl carbamates, with a wide range of nucleophiles at ambient temperature promoted by Ph3CClO4. The metal-free reaction has an excellent functional-group tolerance, and displays a broad scope with respect to both N-carbamates and nucleophile partners (a variety of organoboranes and C-H compounds). The synthetic utility in target- as well as diversity-oriented syntheses is demonstrated. Strategic play: A direct functionalization of the title carbamates with a wide range of nucleophiles has been developed. The reaction proceeds efficiently at low temperature using Ph3CClO4 as an oxidant. Sensitive functional groups are tolerated, thus allowing applications in natural product synthesis, the construction of chemical libraries, and the discovery of potential anticancer targets.