Thermopsine

Base Information

• Chemical Name: Thermopsine
• CAS No.: 486-89-5
• Molecular Formula: C15H20 N2 O
• Molecular Weight: 244.37
• European Community (EC) Number: 689-182-6
• Wikipedia: Anagyrine
• Wikidata: Q104999598
• ChEMBL ID: CHEMBL4752273
• Mol file: 486-89-5.mol

Synonyms:7,7a,8,9,10,11,13,14-octahydro-7,14-memethano-4H,6H-dipyrido(1,2-a:1',2'-e)(1,5)diazocin-4-one;anagyrine

Chemical Property of Thermopsine

Chemical Property:

• Vapor Pressure: 1.73E-08mmHg at 25°C
• Refractive Index: 1.6280 (estimate)
• Boiling Point: 455.6°C at 760 mmHg
• PKA: 9.71±0.20(Predicted)
• Flash Point: 216.3°C
• PSA: 25.24000
• Density: 1.22±0.1 g/cm3 (20 ºC 760 Torr)
• LogP: 1.75780
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 244.157563266
• Heavy Atom Count: 18
• Complexity: 440

Purity/Quality:

95%-98% ^*data from raw suppliers

Anagyrine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CC3CC(C2C1)CN4C3=CC=CC4=O
• Description: An amorphous alkaloid isolated from Thermopsis rhombifolia (Watt), Richards, and also present in Lupinus macounii Rydb. The base forms a perchlorate, m.p. 313°C and a picrate, m.p. 253°C. On catalytic hydrogenation it yields the octahydro derivative, b.p. l40°CjO.2 mm which also forms a perchlorate, m.p. 213°C; [α]D - 40.9° (H20).
• Uses: Anagyrine is a naturally occuring alkaloid found in Genista vuralli, which displays antimicrobial activity.

Technology Process of Thermopsine

There total 34 articles about Thermopsine 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: 92.0%

(1R,9R,10R)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadec-2,4,12-trien-6-one → anagyrine (486-89-5)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In methanol; at 20 ℃; for 2.5h; under 760.051 Torr;

DOI:10.1002/anie.201712852

Reference yield: 85.0%

(+/-)-17-oxoanagyrine → (+/-)-anagyrine (486-89-5,486-90-8,34389-11-2,53584-33-1,55821-71-1)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/anie.200504015

Reference yield: 57.0%

(+/-)-17-oxothermopsine → (+/-)-thermopsine (486-89-5,486-90-8,34389-11-2,53584-33-1,55821-71-1)

Guidance literature:

With borane-THF; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1002/anie.200504015

upstream raw materials:

(+/-)-(7at)-7,7a,8,9,10,11,13,14-octahydro-6H-7r,14c-methano-dipyrido[1,2-a;1',2'-e][1,5]diazocinylium; bromide

2-Pyridone

ethyl 2-[N-benzylpiperidin-2-yl]acrylate

(+/-)-ethyl 3-ethoxy-2-[1-benzylpiperidin-2-yl]propionate

Downstream raw materials:

(+/-)-thermopsine

Refernces

• 1、 Gray, Diane,Gallagher, Timothy. "A flexible strategy for the synthesis of tri- and tetracyclic lupin alkaloids: Synthesis of (+)-cytisine, (±)-anagyrine, and (±)-thermopsine". . p. 2419 - 2423. Retrieved 2007/10/03.