Setoclavine

Base Information

• Chemical Name: Setoclavine
• CAS No.: 519-12-0
• Molecular Formula: C16H18 N2 O
• Molecular Weight: 254.332
• Hs Code.: 2933990090
• UNII: UE9HT9P885
• DSSTox Substance ID: DTXSID301256140
• Nikkaji Number: J13.979C
• Wikidata: Q15633928
• Wikipedia: Setoclavine
• Mol file: 519-12-0.mol

Synonyms:setoclavine

Chemical Property of Setoclavine

Chemical Property:

• Melting Point: 216-222 °C (decomp)(Solv: ethyl ether (60-29-7))
• Boiling Point: 473.6±45.0 °C(Predicted)
• PKA: 13.85±0.20(Predicted)
• PSA: 39.26000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 2.11030
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 254.141913202
• Heavy Atom Count: 19
• Complexity: 421

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(CN(C2CC3=CNC4=CC=CC(=C34)C2=C1)C)O
• Isomeric SMILES: C[C@]1(CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C)O
• Description: An ergot alkaloid from the mycelia of Claviceps purpurea, the base yields colourless prisms when crystallized from Me2CO or MeOH. It is dextrorotatory having [α]20D + 165° (c 0.3, EtOH) or + 174° (c 1.0, CHCI3)' The ultraviolet spectrum in EtOH exhibits two absorption maxima at 243 and 313 mJ.1. The alkaloid forms crystalline salts with mineral acids, e.g. the hydrochloride, m.p. > 300°C and the nitrate, m.p. > 300°C;[α]20D + 190° (c 0.5,50% aqueous EtOH). The nitrogen atoms are present as an imino and a methylimino group.

Technology Process of Setoclavine

There total 4 articles about Setoclavine 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: 38.0%

methyllithium (917-54-4) + (+)-9,10-didehydro-6-methylergoline-8-one (51867-18-6) → (+)-setoclavine (519-12-0) + (+)-isosetoclavine (519-11-9)

Guidance literature:

In tetrahydrofuran; methoxybenzene; at -50 - 0 ℃; for 1h;

DOI:10.3987/COM-05-S(T)26

Reference yield:

agroclavine (548-42-5,194346-16-2) → (+)-setoclavine (519-12-0)

Guidance literature:

With potassium dichromate; sulfuric acid;

Reference yield:

→ Isosetoclavine (519-11-9,519-12-0,6881-99-8,34964-90-4,86194-81-2)

Guidance literature:

CH3-MgBr, Keton 13;

DOI:10.1016/S0040-4020(01)97523-4

upstream raw materials:

agroclavine

methyllithium

(+)-9,10-didehydro-6-methylergoline-8-one

Downstream raw materials:

lysergol

Refernces

• 1、 Moldvai, Istvan,Temesvari-Major, Eszter,Gacs-Baitz, Eszter,Incze, Maria,Doernyei, Gabor,Szantay, Csaba. "New routes to clavine-type ergot alkaloids. Part 1. First total synthesis of three natural products: (+)-setoclavine, (+)-isosetoclavine, (-)-9,10-dihydroisoseto-clavine, and structure correction of the latter". . p. 291 - 298. Retrieved 2007/10/03.