(+)-Meloscine

Base Information

• Chemical Name: (+)-Meloscine
• CAS No.: 24314-51-0
• Molecular Formula: C₁₉H₂₀N₂O
• Molecular Weight: 292.381
• Mol file: 24314-51-0.mol

Synonyms:Meloscine(8CI); (+)-Meloscine; 10H-Indolizino[1',8':2,3,4]cyclopenta[1,2-c]quinolin-6(5H)-one,7a-ethenyl-6a,7,7a,11a,12,13-hexahydro-, [6aS-(6aa,7ab,11ab,13aS*)]-; [6aS-(6aa,7ab,11ab,13aS*)]-7a-Ethenyl-6a,7,7a,11a,12,13-hexahydro-10H-indolizino[1',8':2,3,4]cyclopenta[1,2-c]quinolin-6(5H)-one

Chemical Property of (+)-Meloscine

Chemical Property:

• Melting Point: 172-176 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 485.7±45.0 °C(Predicted)
• PKA: 14.12±0.40(Predicted)
• PSA: 32.34000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 2.78880

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+)-Meloscine

There total 128 articles about (+)-Meloscine 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: 99.0%

rac-(2aR,8bS,11aR)-11-allyl-1,1-divinyl-1,2,2a,3,4,9,10,11a-octahydro-11H-pyrrolo[3',2':2,3]cyclopenta[1,2-c]quinolin-3-one → (+/-)-meloscine (24314-51-0,24314-58-7,119146-60-0,119146-61-1)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; at 60 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol200311y

Reference yield: 89.0%

(3aS*,5aR*,11bR*)-3-allyl-4,4-divinyl-2,3,3a,4,5,5a-hexahydro-1H-pyrrolo[3'',2'':2,3]cyclopenta[1,2-c]quinoline-6(7H)-one → (+/-)-16-epimeloscine (24314-51-0,24314-58-7,119146-60-0,119146-61-1)

Guidance literature:

With Hoveyda-Grubbs catalyst second generation; In toluene; at 60 ℃; for 5h; Inert atmosphere;

DOI:10.1021/ja2042854

Reference yield: 86.0%

(+)-(6bR,12aS,12bS,13aS)-12a-{2-[(2-nitrophenyl)selanyl]ethyl}-7,8,12a,12b,13,13a-hexahydro-10H-indolizino[1',8'-2,3,4]cyclopenta[1,2-c]quinolin-1(2H)-one (1159215-73-2) → meloscine (24314-51-0)

Guidance literature:

(+)-(6bR,12aS,12bS,13aS)-12a-{2-[(2-nitrophenyl)selanyl]ethyl}-7,8,12a,12b,13,13a-hexahydro-10H-indolizino[1',8'-2,3,4]cyclopenta[1,2-c]quinolin-1(2H)-one; With trifluoroacetic acid;

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 - 20 ℃; for 4h;

DOI:10.1002/anie.200800693

upstream raw materials:

(+)-(6bR,12aS,12bS,13aS)-12a-{2-[(2-nitrophenyl)selanyl]ethyl}-7,8,12a,12b,13,13a-hexahydro-10H-indolizino[1',8'-2,3,4]cyclopenta[1,2-c]quinolin-1(2H)-one

ethyl 1,1-bis(benzyloxymethyl)cyclopropane-2-carboxylate

ethyl 2,2-diformylcyclopropanecarboxylate

2,2-divinylcyclopropanecarboxylic acid

Downstream raw materials:

(+/-)-meloscine

Refernces

• 1、 Feldman, Ken S.,Antoline, Joshua F.. "Synthesis studies on the Melodinus alkaloid meloscine". . p. 1434 - 1445. Retrieved 2013/02/25.
• 2、 Zhang, Hanmo,Curran, Dennis P.. "A short total synthesis of (±)-epimeloscine and (±)-meloscine enabled by a cascade radical annulation of a divinylcyclopropane". supporting information; experimental part. p. 10376 - 10378. Retrieved 2011/08/05.