Currayanine

Base Information

• Chemical Name: Currayanine
• CAS No.: 25488-33-9
• Molecular Formula: C₂₃H₂₅NO
• Molecular Weight: 331.458
• NSC Number: 654278
• DSSTox Substance ID: DTXSID501317075
• Nikkaji Number: J1.372.542J
• Wikidata: Q104399765
• Metabolomics Workbench ID: 44308
• ChEMBL ID: CHEMBL1973644

Synonyms:Currayanine;Murrayazolidine;Cyclomahanimbine;Curryanine;NSC654278;CHEMBL1973644;CHEBI:179458;DTXSID501317075;NSC-654278;NCI60_018842;1,2,3,4,5,13-Hexahydro-2-isopropenyl-1,5-methano-5,7-dimethyloxocino[3,2-a]carbazole;1,2,3,4,5,13-Hexahydro-5,7-dimethyl-2-(1-methylethenyl)-1,5-methanooxocino[3,2-a]carbazole, 9CI;13,16-dimethyl-19-(prop-1-en-2-yl)-15-oxa-4-azapentacyclo[14.3.1.0^{2,14}.0^{3,11}.0^{5,10}]icosa-2,5,7,9,11,13-hexaene;13,16-dimethyl-19-prop-1-en-2-yl-15-oxa-4-azapentacyclo[14.3.1.02,14.03,11.05,10]icosa-2(14),3(11),5,7,9,12-hexaene;25488-33-9

Chemical Property of Currayanine

Chemical Property:

• Melting Point: 143°C
• PSA: 25.02000
• LogP: 6.24040
• XLogP3: 6.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 331.193614421
• Heavy Atom Count: 25
• Complexity: 558

Purity/Quality:

99% ,98%,Electron Grade , ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C3=C1OC4(CCC(C3C4)C(=C)C)C)NC5=CC=CC=C52
• Description: The structure of this alkaloid has recently been revised to that shown above.

Technology Process of Currayanine

There total 7 articles about Currayanine 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: 44.0%

mahanimbine (21104-28-9,24948-14-9) → murrayazolinine (49620-01-1) + bicyclomahanimbine (31077-94-8) + murrayazolidine (25488-33-9)

Guidance literature:

With boron trifluoride diethyl etherate; In acetone; at 20 ℃; for 1h; Solvent;

DOI:10.2174/1570178617999200730204856

Reference yield: 6.0%

N,N-dimethyl-formamide (68-12-2,33513-42-7) + (+)-(S)-mahanimbine → curryanin (25488-33-9) + isocyclomahanimbine + bicyclomahanimbine + (S)-3,5-dimethyl-3-(4-methylpent-3-en-1-yl)pyrano[3,2-a]carbazole-11(3H)-carbaldehyde + C24H29NO2 + curryangin + (S)-3-(2-(3,3-dimethyloxiran-2-yl)ethyl)-3,5-dimethylpyrano[3,2-a]carbazole-11(3H)-carbaldehyde + murrayazolinine

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 0 ℃; Inert atmosphere;

(+)-(S)-mahanimbine; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/c6ra16531a

Reference yield:

mahanimbine (21104-28-9,24948-14-9) → Methyl-isopropenylcarbazol (25488-33-9)

Guidance literature:

With ion-exchange resin (H⁺ form); In benzene; Heating;

upstream raw materials:

mahanimbine

N,N-dimethyl-formamide

2-hydroxy-3-methyl-9H-carbazole

(E/Z)-3,7-dimethyl-2,6-octadienal

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