Pergularinine

Base Information

• Chemical Name: Pergularinine
• CAS No.: 571-70-0
• Molecular Formula: C₂₃H₂₅NO₄
• Molecular Weight: 379.456
• NSC Number: 100055
• DSSTox Substance ID: DTXSID90972565
• Nikkaji Number: J145.305J
• Wikidata: Q82956350
• Pharos Ligand ID: UBXAD1Q174PK
• Metabolomics Workbench ID: 133491
• ChEMBL ID: CHEMBL398325
• Mol file: 571-70-0.mol

Synonyms:pergularinine

Chemical Property of Pergularinine

Chemical Property:

• Vapor Pressure: 1.08E-14mmHg at 25°C
• Boiling Point: 588.5°Cat760mmHg
• Flash Point: 309.7°C
• PSA: 51.16000
• Density: 1.31g/cm³
• LogP: 3.96810
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 379.17835828
• Heavy Atom Count: 28
• Complexity: 559

Purity/Quality:

PERGULARININE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C3=C(CN4CCCC4C3O)C5=CC(=C(C=C52)OC)OC
• Isomeric SMILES: COC1=CC2=C(C=C1)C3=C(CN4CCC[C@H]4[C@@H]3O)C5=CC(=C(C=C52)OC)OC

Technology Process of Pergularinine

There total 2 articles about Pergularinine 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:

C23H23NO4 → (13aS,14S)-14-hydroxytylophorine (571-70-0,6799-27-5,52437-07-7,62181-70-8)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; methanol; hexane; at -40 - 20 ℃; for 9h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.200900920

Reference yield:

C23H23NO5 → (13aS,14S)-14-hydroxytylophorine (571-70-0,6799-27-5,52437-07-7,62181-70-8)

Guidance literature:

With borane-THF; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2010.11.008

Reference yield: 96.0%

(13aS,14S)-14-hydroxytylophorine (571-70-0,6799-27-5,52437-07-7,62181-70-8) → (S)-deoxytylophorinine (54781-87-2)

Guidance literature:

With triethylsilane; trifluoroacetic acid; at 20 ℃; for 10h; Darkness;

DOI:10.1002/ejoc.200900920

Downstream raw materials:

(S)-deoxytylophorinine

Refernces

• 1、 Wang, Ziwen,Li, Zheng,Wang, Kailiang,Wang, Qingmin. "Efficient and chirally specific synthesis of phenanthro-indolizidine alkaloids by parham-type cycloacylation". experimental part. p. 292 - 299. Retrieved 2010/03/30.