Neferine

Base Information

• Chemical Name: Neferine
• CAS No.: 2292-16-2
• Molecular Formula: C38H44N2O6
• Molecular Weight: 624.777
• Mol file: 2292-16-2.mol

Synonyms:Neferine(7CI,8CI);(-)-Neferine;4''-O-Methylliensinine;Methylliensinine;Neferin;neferine;

Chemical Property of Neferine

Chemical Property:

• Vapor Pressure: 6.97E-21mmHg at 25°C
• Melting Point: 59-61 °C
• Refractive Index: 1.601
• Boiling Point: 710.931 °C at 760 mmHg
• PKA: 9.28±0.45(Predicted)
• Flash Point: 383.758 °C
• PSA: 72.86000
• Density: 1.186 g/cm³
• LogP: 6.63810
• Storage Temp.: 2-8°C
• Solubility.: DMSO: >15mg/mL

Purity/Quality:

99.5% ^*data from raw suppliers

Neferine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: A bisbenzylisoquinoline alkaloid from Nelumbo nucifera, the structure of this base has been shown to be that represented above based upon chemical degrada_x0002_tive studies and spectroscopic data. Four methoxyl groups, one hydroxyl and two methylimino groups are present.
• Uses: Neferine is an isoquinoline alkaloid which enhances the antitumor effect of Mitomycin-C in hela cells through activation of p38-MAPK. Useful in the treatment of cervical cancers.

Technology Process of Neferine

There total 12 articles about Neferine 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: 84.0%

(S)-1-(4-(benzyloxy)-3-((R)-6-methoxy-1-(4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yloxy)benzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline (1438250-78-2) → 1'-epi-neferine (2292-16-2)

Guidance literature:

(S)-1-(4-(benzyloxy)-3-((R)-6-methoxy-1-(4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-yloxy)benzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline; With boron trichloride; In dichloromethane; at -15 ℃; for 1h;

With ammonia; water; In dichloromethane;

DOI:10.1248/cpb.c12-00820

Reference yield:

→ neferine (2292-16-2)

Guidance literature:

O-Acetylderivat IX, NaOH/CH3OH;

Reference yield:

(1R)-7-(benzyloxy)-2-[(4S)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-6-methoxy-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydroisoquinoline (1438250-58-8) → 1'-epi-neferine (2292-16-2)

Guidance literature:

Multi-step reaction with 5 steps

1: toluene-4-sulfonic acid; hydrazine hydrate / ethanol / 2 h / Reflux

2: sodium tetrahydroborate / methanol; water / 0 - 20 °C

3: palladium 10% on activated carbon; acetic acid; hydrogen / methanol / 7 h / 20 °C

4: pyridine; copper(I) bromide dimethylsulfide complex; caesium carbonate / 20 h / Reflux

5: boron trichloride / dichloromethane / 1 h / -15 °C

With pyridine; sodium tetrahydroborate; copper(I) bromide dimethylsulfide complex; palladium 10% on activated carbon; hydrogen; boron trichloride; caesium carbonate; toluene-4-sulfonic acid; hydrazine hydrate; acetic acid; In methanol; ethanol; dichloromethane; water; 4: |Ullmann Condensation;

DOI:10.1248/cpb.c12-00820

upstream raw materials:

(1R)-7-(benzyloxy)-2-[(4S)-4,5-dihydro-4-(1-methylethyl)-2-oxazolyl]-6-methoxy-1-(4-methoxy-benzyl)-1,2,3,4-tetrahydroisoquinoline

(R)-7-(benzyloxy)-6-methoxy-1-(4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinoline

(S)-1-(4-(benzyloxy)-3-bromobenzyl)-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline

(R)-6-methoxy-1-(4-methoxybenzyl)-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-ol

Refernces