Hernandezine

Base Information

• Chemical Name: Hernandezine
• CAS No.: 6681-13-6
• Molecular Formula: C39H44N2O7
• Molecular Weight: 652.788
• UNII: HPH24MXX7G
• DSSTox Substance ID: DTXSID40216926
• Nikkaji Number: J12.754J
• Wikipedia: Hernandezine
• Wikidata: Q15410998
• Pharos Ligand ID: 8ANZF28DUMXT
• ChEMBL ID: CHEMBL504936
• Mol file: 6681-13-6.mol

Synonyms:hernandezine

Chemical Property of Hernandezine

Chemical Property:

• Melting Point: 192-193℃
• Boiling Point: 732.8±60.0 °C(Predicted)
• PKA: 7.69±0.20(Predicted)
• PSA: 71.09000
• Density: 1.175±0.06 g/cm3 (20 ºC 760 Torr)
• LogP: 7.04680
• XLogP3: 6.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 652.31485175
• Heavy Atom Count: 48
• Complexity: 1030

Purity/Quality:

95%-98% ^*data from raw suppliers

Hernandezine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C3C=C2C1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)CC6C7=C(CCN6C)C(=C(C(=C7O3)OC)OC)OC)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C3C=C2[C@@H]1CC4=CC=C(C=C4)OC5=C(C=CC(=C5)C[C@H]6C7=C(CCN6C)C(=C(C(=C7O3)OC)OC)OC)OC)OC
• Uses: Hernandezine is a novel anticancer AMPK activator identified as a major major active constituent of Thalictrum Ranunculaceae.

Technology Process of Hernandezine

There total 6 articles about Hernandezine 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:

C38H42N2O7 + carbonic acid dimethyl ester (616-38-6) → Hernandezine (6681-13-6)

Guidance literature:

In ethyl acetate; N,N-dimethyl-formamide; at 50 ℃; for 2h;

Reference yield:

Tetrandrin (518-34-3,5990-67-0) → Hernandezine (6681-13-6)

Guidance literature:

Multi-step reaction with 3 steps

1: Br₂, AcOH, CF₃CO₂H / H₂O / 0.08 h / Heating

2: (i) nBuLi, (ii) PhNO₂

With bromine; acetic acid; trifluoroacetic acid; In water;

DOI:10.1021/jo00433a019

Reference yield:

fangchinoline (436-77-1,10172-02-8,33889-68-8,38769-07-2,53834-87-0,119478-08-9) → Hernandezine (6681-13-6)

Guidance literature:

Multi-step reaction with 3 steps

1: trifluoroacetic acid; N-Bromosuccinimide / 0 °C

2: copper(I) bromide / N,N-dimethyl-formamide / 5 h / 120 °C / Inert atmosphere

3: N,N-dimethyl-formamide; ethyl acetate / 2 h / 50 °C

With N-Bromosuccinimide; trifluoroacetic acid; copper(I) bromide; In ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

diazomethane

thalidezine

tetrandrine bromide

Tetrandrin