Akuammigine

Base Information

• Chemical Name: Akuammigine
• CAS No.: 642-17-1
• Molecular Formula: C21H24 N2 O3
• Molecular Weight: 352.433
• UNII: 1E21YYE0UM
• DSSTox Substance ID: DTXSID001318228
• Nikkaji Number: J13.574G
• Wikidata: Q27252310
• Pharos Ligand ID: 6YFBSBFMLKDU
• Metabolomics Workbench ID: 122901
• ChEMBL ID: CHEMBL122404
• Mol file: 642-17-1.mol

Synonyms:19-epiajmalicine;ajmalicine;ajmalicine hydrochloride;ajmalicine, (19alpha,20alpha)-isomer;ajmalicine, (19beta)-isomer;ajmalicine, (19beta,20alpha)-isomer;ajmalicine, (3-beta,19beta)-isomer;ajmalicine, (3beta,19alpha)-isomer;ajmalicine, (3beta,19alpha,20alpha)-isomer;ajmalicine, (hydrochloride(19beta,20alpha))-isomer;ajmalicine, hydrochloride(19alpha)-isomer;ajmalicine, PO4(19alpha)-isomer;akuammigine;delta-yohimbine;Lamuran;raubasine;raubasine HCl;raubasine hydrochloride;rauvasan;tetrahydro-alstonine;tetrahydroalstonine

Chemical Property of Akuammigine

Chemical Property:

• Melting Point: 122-124 °C
• Boiling Point: 524.0±50.0 °C(Predicted)
• PKA: 18.03±0.60(Predicted)
• PSA: 54.56000
• Density: 1.30±0.1 g/cm3(Predicted)
• LogP: 3.11670
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 352.17869263
• Heavy Atom Count: 26
• Complexity: 606

Purity/Quality:

≥98% ^*data from raw suppliers

Akuammigine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C2CN3CCC4=C(C3CC2C(=CO1)C(=O)OC)NC5=CC=CC=C45
• Isomeric SMILES: C[C@H]1[C@@H]2CN3CCC4=C([C@H]3C[C@@H]2C(=CO1)C(=O)OC)NC5=CC=CC=C45

Technology Process of Akuammigine

There total 66 articles about Akuammigine 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: 60.0%

C23H26N2O6 → (+)-rauniticine (483-03-4,483-04-5,642-17-1,5299-09-2,6474-90-4,6870-40-2,6884-17-9,20361-85-7,20361-86-8,24196-06-3,24196-08-5,24196-15-4,24196-16-5,25532-45-0,25532-46-1,112835-69-5,122441-12-7,132016-16-1)

Guidance literature:

C₂₃H₂₆N₂O₆; With methanol; sodium tetrahydroborate; at -10 ℃; for 0.5h; Inert atmosphere;

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 8h; Inert atmosphere; Reflux;

With methanol; potassium carbonate; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.chempr.2017.04.007

Reference yield: 40.0%

dimethyl sulfoxide (67-68-5,8070-53-9) + 2-deoxoisopteropodine (83541-47-3) → N(a)-methylthiomethyl-2-deoxoisopteropodine (83482-71-7) + tetrahydroalstonine (6474-90-4) + akuammigine (642-17-1)

Guidance literature:

With oxalyl dichloride; triethylamine; In dichloromethane; for 1h; temperature: allowed to warm from -78 deg C;

Reference yield: 40.0%

2-deoxoisopteropodine (83541-47-3) → N(a)-methylthiomethyl-2-deoxoisopteropodine (83482-71-7) + tetrahydroalstonine (6474-90-4) + akuammigine (642-17-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; for 1h; temperature: allowed to warm from -78 deg C;

upstream raw materials:

2,3-seco-2,3-dihydroakuammigine

dimethyl sulfoxide

2-deoxoisopteropodine

2-deoxopteropodine

Downstream raw materials:

tetrahydroalstonine

Refernces

• 1、 Martin, Stephen F.,Benage, Brigitte,Geraci, Leo S.,Hunter, James E.,Mortimore, Michael. "Unified strategy for synthesis of indole and 2-oxindole alkaloids". . p. 6161 - 6171. Retrieved 2007/10/02.
• 2、 Calverley, Martin J.. "Chloroformate Ester-induced Reductive 1,2-Bond Cleavage of 1,2,3,4-Tetrahydro-β-carboline Derivatives: Stereochemistry and Application in Sequence with an Oxidative Bond Regeneration Reaction to the Synthesis of Indole Alkaloids". . p. 1848 - 1890. Retrieved 2007/10/02.