Pleiocarpamine

Base Information

• Chemical Name: Pleiocarpamine
• CAS No.: 6393-66-4
• Molecular Formula: C₂₀H₂₂N₂O₂
• Molecular Weight: 322.407
• NSC Number: 374523
• UNII: 4J3PV95ANL
• DSSTox Substance ID: DTXSID80419616
• Wikipedia: Pleiocarpamine
• Wikidata: Q15425259
• Metabolomics Workbench ID: 131355
• ChEMBL ID: CHEMBL3338254
• Mol file: 6393-66-4.mol

Synonyms:pleiocarpamine

Chemical Property of Pleiocarpamine

Chemical Property:

• Vapor Pressure: 8E-10mmHg at 25°C
• Melting Point: 159°C
• Boiling Point: 492°C at 760 mmHg
• Flash Point: 251.3°C
• PSA: 34.47000
• Density: 1.36g/cm³
• LogP: 3.17230
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 322.168127949
• Heavy Atom Count: 24
• Complexity: 574

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C1CN2CCC3=C4C2CC1C(N4C5=CC=CC=C35)C(=O)OC
• Isomeric SMILES: C/C=C\1/CN2CCC3=C4[C@@H]2C[C@@H]1[C@H](N4C5=CC=CC=C35)C(=O)OC
• Description: This carboline alkaloid is present in the bark of Hunteria eburnea Pichon and the roots of Pleiocarpa rnutica Benth. The ultraviolet spectrum has absorption maxima at 230 and 285 mil and the alkaloid is dextrorotatory with [α]21D + 136° (c 0.74, MeOH).

Technology Process of Pleiocarpamine

There total 55 articles about Pleiocarpamine 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: 86.0%

(E)-3-ethylidene-13-(methoxycarbonyl)-1,3,4,6,7,12b-hexahydro-2,12-methanoindolo[2,3-a]quinolizine 5(2H)-borate → (±)-pleiocarpamine + (+/-)-epi-pleiocarpamine (6393-66-4,60325-74-8,80249-86-1)

Guidance literature:

With trimethylamine-N-oxide; In methanol; at 20 ℃; for 4h; Inert atmosphere; Reflux;

DOI:10.1021/acs.orglett.9b01084

Reference yield: 62.0%

(2S,12bS,13R,E)-methyl 3-ethylidene-13-formyl-2,3,4,6,7,12b-hexahydro-1H-2,12-methanoindolo[2,3-a]quinolizine-13-carboxylate → (+)-16-epi-pleiocarpamine (6393-66-4,60325-74-8,80249-86-1)

Guidance literature:

With potassium carbonate; In methanol; at 50 ℃; for 3.5h; Reagent/catalyst;

DOI:10.1002/ejoc.202000962

Reference yield: 57.0%

(2S,12bS,13R,E)-methyl 3-ethylidene-13-(hydroxymethyl)-2,3,4,6,7,12b-hexahydro-1H-2,12-methanoindolo[2,3-a]quinolizine-13-carboxylate (180869-66-3) → (+)-16-epi-pleiocarpamine (6393-66-4,60325-74-8,80249-86-1)

Guidance literature:

With sodium hydride; In toluene; mineral oil; for 4h; Reflux;

DOI:10.1002/ejoc.202000962

upstream raw materials:

20E-[3S^*-(3α,15α)]-3,4,5,6,14,15,21-heptahydro-15-(methyl acetate)-20-ethylidene-indolo[2,3-a]quinolizine

(Z)-methyl 2-((2S,12bS,E)-3-ethylidene-1,2,3,4,6,7,12,12b-octahydroindolo[2,3-a]quinolizin-2-yl)-3-hydroxyacrylate

(Z,2R,12bS)-tert-butyl 2-[di(methoxycarbonyl)methyl]-3-ethylidene-1,2,3,4,6,7-hexahydroindolo[2,3-a]quinolizine-12(12bH)-carboxylate

D-tryptophan

Downstream raw materials:

villalstonine

(±)-C-mavacurine

C₂₀H₂₅N₂O⁽¹⁺⁾*I^(1-)

macrocarpamine

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