3'-Demethoxypiplartine

Base Information

• Chemical Name: 3'-Demethoxypiplartine
• CAS No.: 130263-10-4
• Molecular Formula: C16H17 N O4
• Molecular Weight: 287.315
• ChEMBL ID: CHEMBL4066386
• Metabolomics Workbench ID: 70957
• Nikkaji Number: J865.603G,J2.773.240B
• Mol file: 130263-10-4.mol

Synonyms:3'-Demethoxypiplartine;Demethoxypiplartine;C10444;ZINC14658397;CHEMBL4066386;SCHEMBL17472036;HY-N1817;AKOS040761086;FS-8694;NP-003715;CS-0017671;(E)-1-(3-(3,4-Dimethoxyphenyl)acryloyl)-5,6-dihydropyridin-2(1H)-one;1-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-2,3-dihydropyridin-6-one

Chemical Property of 3'-Demethoxypiplartine

Chemical Property:

• Vapor Pressure: 2.97E-09mmHg at 25°C
• Melting Point: 116-117℃ (methanol )
• Boiling Point: 476.8°Cat760mmHg
• Flash Point: 242.1°C
• PSA: 55.84000
• Density: 1.194g/cm³
• LogP: 1.97000
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 287.11575802
• Heavy Atom Count: 21
• Complexity: 444

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

3'-Demethoxypiplartine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)C=CC(=O)N2CCC=CC2=O)OC
• Isomeric SMILES: COC1=C(C=C(C=C1)/C=C/C(=O)N2CCC=CC2=O)OC

Technology Process of 3'-Demethoxypiplartine

There total 4 articles about 3'-Demethoxypiplartine 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: 58.0%

→ (E)-1-(3-(3,4-dimethoxylphenyl)prop-2-enoyl)-5,6-dihydropyridin-2(1H)-one (130263-10-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

In tetrahydrofuran; for 1h;

Reference yield:

5,6-dihydro-2(1H)-pyridinone (6052-73-9) + C16H20O5 → (E)-1-(3-(3,4-dimethoxylphenyl)prop-2-enoyl)-5,6-dihydropyridin-2(1H)-one (130263-10-4)

Guidance literature:

5,6-dihydro-2(1H)-pyridinone; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.75h; Inert atmosphere;

C₁₆H₂₀O₅; In tetrahydrofuran; for 1h; Inert atmosphere;

DOI:10.1016/j.ejmech.2016.09.048

Reference yield:

3,4-dimethoxy-trans-cinnamic acid (14737-89-4) → (E)-1-(3-(3,4-dimethoxylphenyl)prop-2-enoyl)-5,6-dihydropyridin-2(1H)-one (130263-10-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / tetrahydrofuran / 0.75 h / -20 °C

2.1: n-butyllithium / tetrahydrofuran / 0.75 h / -78 °C / Inert atmosphere

2.2: 1 h / Inert atmosphere

With n-butyllithium; triethylamine; In tetrahydrofuran;

DOI:10.1016/j.ejmech.2016.09.048

upstream raw materials:

5,6-dihydro-2(1H)-pyridinone

N-(but-3-en-1-yl)prop-2-enamide

3,4-dimethoxy-trans-cinnamic acid

Refernces

• 1、 Meegan, Mary J.,Nathwani, Seema,Twamley, Brendan,Zisterer, Daniela M.,O'Boyle, Niamh M.. "Piperlongumine (piplartine) and analogues: Antiproliferative microtubule-destabilising agents". . p. 453 - 463. Retrieved 2016/10/04.