(R)-N-Methylcoclaurine

Base Information

• Chemical Name: (R)-N-Methylcoclaurine
• CAS No.: 5096-70-8
• Molecular Formula: C18H21NO3
• Molecular Weight: 299.37
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID80198974
• Nikkaji Number: J564.027J
• Wikidata: Q27101882
• Metabolomics Workbench ID: 68700
• Mol file: 5096-70-8.mol

Synonyms:(R)-N-Methylcoclaurine;5096-70-8;(-)-N-methylcoclaurine;1betaH-Coclaurine, 2-methyl-;(1R)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-3,4-dihydro-1H-isoquinolin-7-ol;(-)-1(R)-N-Methylcoclaurine;C05243;7-Isoquinolinol, 1,2,3,4-tetrahydro-1-((4-hydroxyphenyl)methyl)-6-methoxy-2-methyl-, (R)-;(R)-1,2,3,4-Tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-7-isoquinolinol;AC1L99LI;SCHEMBL18179206;CHEBI:16387;DTXSID80198974;HY-N7717;AKOS040762086;CS-0135675;Q27101882;(1R)-1-(4-hydroxybenzyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol;7-Isoquinolinol, 1,2,3,4-tetrahydro-1-[(4-hydroxyphenyl)methyl]-6-methoxy-2-methyl-, (1R)-

Chemical Property of (R)-N-Methylcoclaurine

Chemical Property:

• Vapor Pressure: 7.14E-10mmHg at 25°C
• Melting Point: 184-185℃
• Boiling Point: 480.9°C at 760 mmHg
• PKA: 10.00±0.15(Predicted)
• Flash Point: 244.6°C
• PSA: 52.93000
• Density: 1.214g/cm³
• LogP: 2.81600
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 299.15214353
• Heavy Atom Count: 22
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C=C2C1CC3=CC=C(C=C3)O)O)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C=C2[C@H]1CC3=CC=C(C=C3)O)O)OC

Technology Process of (R)-N-Methylcoclaurine

There total 11 articles about (R)-N-Methylcoclaurine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(-)-OO'-dibenzylcoclaurine (38474-17-8,38474-19-0,47765-29-7,114909-85-2) → (-)-(R)-(N)-methylcoclaurine (5096-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 105 mg / H₂ / palladium-carbon / ethanol

2: 60 mg / aq. NaOH, formic acid / H₂O / 0.25 h / 100 °C

With sodium hydroxide; formic acid; hydrogen; palladium on activated charcoal; In ethanol; water;

DOI:10.1039/P19810002598

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (+)-coclaurine hydrochloride (3422-42-2,17934-80-4,19894-19-0) → (-)-(R)-(N)-methylcoclaurine (5096-70-8)

Guidance literature:

With sodium hydroxide; formic acid; In water; at 100 ℃; for 0.25h;

DOI:10.1039/P19810002598

Reference yield:

(S,R)-hayatidin (16543-77-4) → (-)-(R)-(N)-methylcoclaurine (5096-70-8)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether; methanol

2: 84 mg / Na, liquid ammonia / toluene / 1) -60 deg C, 3 h, 2) room temperature, 20 h

With ammonia; sodium; In methanol; diethyl ether; toluene;

DOI:10.1016/S0040-4020(01)81679-3

upstream raw materials:

pheanthine

formaldehyd

(+)-coclaurine hydrochloride

O-methyl-hayatidin

Refernces

• 1、 Bhakuni,Dewan S.,Jain,Sudha,Chaturvedi,Rekha. "THE BIOSYNTHESIS OF THE ALKALOIDS OF CISSAMPELOS PAREIRA LINN". . p. 3975 - 3982. Retrieved 2007/10/02.
• 2、 Bhakuni, Dewan S.,Jain, Sudha. "THE BIOSYNTHESIS OF THE ALKALOIDS OF CROTON SPARSIFLORUS MORONG". . p. 3175 - 3182. Retrieved 2007/10/02.