Kurchessine

Base Information

• Chemical Name: Kurchessine
• CAS No.: 6869-45-0
• Molecular Formula: C25H44N2
• Molecular Weight: 372.638
• UNII: 618227L15H
• DSSTox Substance ID: DTXSID30332028
• Nikkaji Number: J15.155F
• Wikidata: Q27107104
• Metabolomics Workbench ID: 131973
• ChEMBL ID: CHEMBL344384
• Mol file: 6869-45-0.mol

Synonyms:Kurchessine;Irehdiamine I;Sarcodinine;Kurchessine [MI];6869-45-0;UNII-618227L15H;CHEBI:6145;CHEMBL344384;618227L15H;(3beta,20S)-N,N,N,N-Tetramethylpregn-5-ene-3,20-diamine;Pregn-5-ene-3,20-diamine, N3,N3,N20,N20-tetramethyl-, (3beta,20S)-;Pregn-5-ene-3.beta.,20.alpha.-diamine, N,N,N',N'-tetramethyl-;Pregn-5-ene-3,20-diamine, N,N,N',N'-tetramethyl-, (3.beta.,20S)-;(3S,8S,9S,10R,13S,14S,17S)-17-((S)-1-(dimethylamino)ethyl)-N,N,10,13-tetramethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-amine;(3S,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine;Kurchessin;C10813;SCHEMBL2230965;DTXSID30332028;BDBM50421628;3.beta.,20.alpha.-Bis(dimethylamino)pregn-5-ene;Q27107104;(3.BETA.,20S)-N,N,N,N-TETRAMETHYLPREGN-5-ENE-3,20-DIAMINE;PREGN-5-ENE-3,20-DIAMINE, N3,N3,N20,N20-TETRAMETHYL-, (3.BETA.,20S)-

Chemical Property of Kurchessine

Chemical Property:

• Vapor Pressure: 3.59E-08mmHg at 25°C
• Melting Point: 140-141° (from acetone)
• Boiling Point: 446.6°C at 760 mmHg
• Flash Point: 195.6°C
• PSA: 6.48000
• Density: 0.99g/cm³
• LogP: 5.44570
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 372.350449412
• Heavy Atom Count: 27
• Complexity: 593

Purity/Quality:

KURCHESSINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)N(C)C)C)C)N(C)C
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)N(C)C)C)C)N(C)C
• Description: A pregnene alkaloid found in the bark of Holarrhena antidysenterica Wall. and also present in the leaves of Sarcococca pruni!ormis Lindl., the base forms colour_x0002_less crystals from Me2CO and has [α]20D - 37° (c 1.90, CHCl3), - 17° (c 1.OS, MeOH). It contains three methyl groups and two dimethylamino groups in the molecule. The alkaloid is characterized as the crystalline perchlorate, m.p. 277- 9°C (dec.) or the picrate, m.p. 228-230°C. The structure has been established as 3 ,20 -bis (dimethylamino)pregn-S-ene. It is identical with saracodinine.

Technology Process of Kurchessine

There total 14 articles about Kurchessine 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:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3β,20α-diamino-pregn-5-ene (3614-57-1) → Kurchessin (6869-45-0)

Guidance literature:

With formic acid;

DOI:10.1007/s12039-012-0346-x

Reference yield:

regholarrhenine F (10308-37-9,124162-08-9) → kurchessine (6788-33-6,6869-45-0,17934-41-7,17934-43-9,33467-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CrO₃ / acetic acid / 24 h / Ambient temperature

2: Wolff-Kishner reduction

With chromium(VI) oxide; In acetic acid;

DOI:10.1016/0031-9422(90)80057-N

Reference yield:

→ Kurchessin (6869-45-0)

Guidance literature:

With potassium hydroxide; hydrazine hydrate; 2,2'-[1,2-ethanediylbis(oxy)]bisethanol; at 215 ℃;

upstream raw materials:

formaldehyd

N³-methyl-pregn-5-ene-3β,20α_F-diyldiamine

3β,20α-diamino-pregn-5-ene

3β,20β-diamino-pregn-5-ene

Refernces

• 1、 Bhutani, K. K.,Vaid, R. M.,Ali, M.,Kapoor, R.,Soodan, S. R.,Kumar, D.. "STEROIDAL ALKALOIDS FROM HOLARRHENA ANTIDYSENTERICA". . p. 969 - 972. Retrieved 2007/10/02.