Cryptopleurine

Base Information

• Chemical Name: Cryptopleurine
• CAS No.: 482-22-4
• Molecular Formula: C₂₄H₂₇NO₃
• Molecular Weight: 377.483
• NSC Number: 19912
• UNII: 3JZK58H75B
• DSSTox Substance ID: DTXSID3075414
• Nikkaji Number: J57.974B
• Wikidata: Q27106253
• Metabolomics Workbench ID: 68010
• ChEMBL ID: CHEMBL198075
• Mol file: 482-22-4.mol

Synonyms:cryptopleurine;cryptopleurine, (+-)-isomer

Chemical Property of Cryptopleurine

Chemical Property:

• Vapor Pressure: 2.61E-12mmHg at 25°C
• Boiling Point: 553.9°Cat760mmHg
• Flash Point: 159.5°C
• PSA: 30.93000
• Density: 1.23g/cm³
• LogP: 4.86730
• XLogP3: 5.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 377.19909372
• Heavy Atom Count: 28
• Complexity: 542

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)C3=C(CC4CCCCN4C3)C5=CC(=C(C=C52)OC)OC
• Isomeric SMILES: COC1=CC2=C(C=C1)C3=C(C[C@H]4CCCCN4C3)C5=CC(=C(C=C52)OC)OC
• Uses: Cryptopleurine is a phenanthroindolizidine alkaloid with anti-cancer therapeutic potentials.

Technology Process of Cryptopleurine

There total 62 articles about Cryptopleurine 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: 94.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (R)-2-((2,3,6-trimethoxyphenanthren-10-yl)methyl)piperidine (697234-86-9) → (R)-(-)-cryptopleurine (482-21-3,482-22-4,23365-52-8,87302-53-2,100295-90-7)

Guidance literature:

With hydrogenchloride; In ethanol; water; for 11h; Reflux; Darkness;

DOI:10.1021/jo500013e

Reference yield: 80.0%

(R)-(-)-Julandine → (R)-(-)-cryptopleurine (482-21-3,482-22-4,23365-52-8,87302-53-2,100295-90-7)

Guidance literature:

With vanadium(V) oxytrifluoride; trifluoroacetic anhydride; In dichloromethane; ethyl acetate; at -78 ℃; for 2h; Inert atmosphere;

DOI:10.1055/s-0031-1290457

Reference yield: 79.0%

C36H34N2O4S → (R)-(-)-cryptopleurine (482-21-3,482-22-4,23365-52-8,87302-53-2,100295-90-7)

Guidance literature:

C₃₆H₃₄N₂O₄S; With dmap; trifluoromethylsulfonic anhydride; In dichloromethane; at 0 - 20 ℃; for 16h; Inert atmosphere;

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Reflux;

DOI:10.1002/ejoc.201300200

upstream raw materials:

11,12,13,14,14a,15-Hexahydro-2,3,6-trimethoxy-9H-phenanthro<9,10-b>quinolizin-9-one

formaldehyd

(R)-2-((2,3,6-trimethoxyphenanthren-10-yl)methyl)piperidine

10-(bromomethyl)-2,3,6-trimethoxyphenanthrene

Refernces

• 1、 Stoye, Alexander,Opatz, Till. "Synthesis of (-)-cryptopleurine by combining gold(I) catalysis with a free radical cyclization". . p. 2149 - 2156. Retrieved 2015/04/14.
• 2、 Liéby-Muller, Frédéric,Marion, Frédéric,Schmitt, Philippe,Annereau, Jean-Philippe,Kruczynski, Anna,Guilbaud, Nicolas,Bailly, Christian. "Synthesis and biological evaluation of (-)-6-O-desmethylcryptopleurine and analogs". . p. 184 - 187. Retrieved 2015/04/13.