Oxysparteine

Base Information

• Chemical Name: Oxysparteine
• CAS No.: 489-72-5
• Molecular Formula: C15H24 N2 O
• Molecular Weight: 248.368
• NSC Number: 127496
• DSSTox Substance ID: DTXSID50871686
• Wikidata: Q104396146
• Mol file: 489-72-5.mol

Synonyms:Oxosparteine;MLS002919946;NSC127496;Spartein-10-one;Aphylline;11-Epiaphylline;Spartein-10-one #;Oxyspartein;7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-E][1,5]diazocin-6-one, dodecahydro-, [7R-(7.alpha.,7a.alpha.,14.alpha.,14a.beta.)]-;SPARTEINE, 17-OXO;SCHEMBL11465158;DTXSID50871686;YQMWQSMYVPLYDI-UHFFFAOYSA-N;7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-6-one, dodecahydro-, [7R-(7.alpha.,7a.alpha.,14.alpha.,14a.alpha.)]-;7,14-Methano-2H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-6-one, dodecahydro-, [7R-(7.alpha.,7a.beta.,14.alpha.,14a.alpha.)]-;SMR001797545;7,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-6-one, dodecahydro-, [7R-(7.alpha.,7a.alpha.,14.alpha.,14a.beta.)]-

Chemical Property of Oxysparteine

Chemical Property:

• Vapor Pressure: 1.67E-06mmHg at 25°C
• Boiling Point: 396.7°Cat760mmHg
• Flash Point: 172.7°C
• PSA: 23.55000
• Density: 1.16g/cm³
• LogP: 1.74750
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 248.188863393
• Heavy Atom Count: 18
• Complexity: 356

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CC3CC(C2C1)C(=O)N4C3CCCC4

Technology Process of Oxysparteine

There total 29 articles about Oxysparteine 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: 77.0%

[7S-(7α,7aα,14α,14aβ)]-dodecahydro-7,14-methano-2H,6H-dihydro[1,2-a:1',2'-e]-[1,5]-diazocine sulphate → (-)-17-oxosparteine (489-72-5,577-37-7,1218-51-5,6871-54-1,29882-72-2,82109-83-9,131829-31-7)

Guidance literature:

With sodium hydroxide; potassium hexacyanoferrate(III);

DOI:10.1515/znb-2002-0514

Reference yield: 69.0%

sparteine (90-39-1,446-95-7,492-06-8,492-08-0,4985-24-4,6838-37-5,6917-37-9,24915-04-6,88269-31-2) → 17-oxosparteine (489-72-5,577-37-7,1218-51-5,6871-54-1,29882-72-2,82109-83-9,131829-31-7)

Guidance literature:

With DBN; oxygen; rose bengal; In N,N-dimethyl-formamide; at 20 ℃; for 16h; Irradiation;

DOI:10.1021/acscatal.8b01897

Reference yield:

lupanine perchlorate (6376-21-2,7400-11-5,14691-01-1,18783-52-3,61740-19-0,76030-37-0) → 17-oxosparteine (489-72-5,577-37-7,1218-51-5,6871-54-1,29882-72-2,82109-83-9,131829-31-7)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, / PtO₂, / aq. HCl / 15 h / 1034.3 Torr

2: 60 mg / potassium ferricyanide, 10percent NaOH, / aq. HCl / 0.67 h

With sodium hydroxide; hydrogen; potassium hexacyanoferrate(III); platinum(IV) oxide; In hydrogenchloride;

DOI:10.1139/v88-280

upstream raw materials:

(9aR)-3c-((S)-[2]piperidyl)-(9ar)-octahydro-quinolizin-1c-carboxylic acid ; dihydrochloride

(7R)-(7at)-3,4,7,7a,8,9,10,11,13,14-decahydro-2H-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocin-6-one

(9aR)-3c-((S)-[2]piperidyl)-(9ar)-octahydro-quinolizin-1c-carboxylic acid

(7ac)-3,4,7,7a,8,9,10,11,13,14-decahydro-2H-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocin-6-one

Downstream raw materials:

6,13-Dioxo-spartein

17-phenyl-16,17-dehydrosparteinium hydroxide

Refernces

INDIRECT ELECTROCHEMICAL α-METHOXYLATION OF ALIPHATIC ETHERS AND ACETALS - REACTIVITY AND REGIOSELECTIVITY OF THE ANODIC OXIDATION USING TRIS(2,4-DIBROMOPHENYL)AMINE AS REDOX CATALYST

10.1016/S0040-4020(01)87786-3

The research focuses on the indirect electrochemical α-methoxylation of aliphatic ethers and acetals, a process that is technologically significant for the formation of mixed acetals, aldehydes, or ortho-esters. The study utilizes tris(2,4-dibromophenyl)amine as a redox catalyst in methanol solution, which allows the reaction to occur at low potentials with an undivided cell, leading to higher regioselectivity compared to direct electrolysis without a catalyst. The method is particularly valuable for the regioselective methoxylation of secondary carbon atoms in the presence of primary or tertiary ones and for the acetal carbon in 1,3-dioxolanes. The redox catalyst's stability under reaction conditions enables more than a thousand turnovers. The conclusions highlight the superiority of the indirect electrochemical method in terms of regioselectivity and the potential for large-scale applications, as demonstrated by the successful large-scale electrolysis of 1,2-dimethoxy ethane.