Lunacridine

Base Information

• Chemical Name: Lunacridine
• CAS No.: 83-58-9
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• UNII: 2LL4O86GNH
• DSSTox Substance ID: DTXSID90232111
• Nikkaji Number: J8.615K
• Wikidata: Q27107245
• Metabolomics Workbench ID: 69518
• Mol file: 83-58-9.mol

Synonyms:lunacridine

Chemical Property of Lunacridine

Chemical Property:

• Vapor Pressure: 7.28E-09mmHg at 25°C
• Melting Point: 86-87°
• Boiling Point: 449.4°C at 760 mmHg
• Flash Point: 225.6°C
• PSA: 60.69000
• Density: 1.18g/cm³
• LogP: 2.11510
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 305.16270821
• Heavy Atom Count: 22
• Complexity: 446

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(CC1=C(C2=C(C(=CC=C2)OC)N(C1=O)C)OC)O
• Isomeric SMILES: CC(C)[C@@H](CC1=C(C2=C(C(=CC=C2)OC)N(C1=O)C)OC)O
• Description: This alkaloid was first described by Boorsma who obtained it from the bark of Lunasia costulata Miq (Syn. L. amara Blanco). The base is a quinolone derivative and crystallizes as colourless needles from AcOEt. It is dextrorotatory having [α]24D + 30.1 ° and [α]24436 + 81.8°. Boorsma gives a specific rotation of [α]28D + 31.6°. The solutions of the alkaloid show a weak blue fluorescence in artificial light. A crystalline perchlorate is known, m.p. 146-8°C and 193-5°C after intermediate solidification. This salt is also dextrorotatory with [α]2558925436+ 60.7°. The structure has been demonstrated to be 3-(2-hydroxy-3- methylbutyl)-4: 8-dimethoxy-l-methyl-2-quinolone. The alkaloid described under this name by Dieterle and Beyl appears to be identical with lunamarine (q.v.).

Technology Process of Lunacridine

There total 20 articles about Lunacridine 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: 64.0%

3-((R)-2-Hydroxy-3-methyl-butyl)-4,8-dimethoxy-1H-quinolin-2-one (160024-36-2) + methyl iodide (74-88-4) → lunacridine (83-58-9,52306-35-1,103303-14-6)

Guidance literature:

With potassium carbonate; In acetone; for 1h; Heating;

DOI:10.1016/S0040-4020(01)89424-2

Reference yield: 42.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 3-((R)-2-Hydroxy-3-methyl-butyl)-4,8-dimethoxy-1H-quinolin-2-one (160024-36-2) → lunacridine (83-58-9,52306-35-1,103303-14-6)

Guidance literature:

In methanol; diethyl ether; for 24h;

Reference yield:

→ lunacridine (83-58-9,52306-35-1,103303-14-6)

Guidance literature:

With methanol; sodium hydroxide; water;

DOI:10.1021/ja01517a032

upstream raw materials:

diazomethane

4-hydroxy-3-((R)-2-hydroxy-3-methyl-butyl)-8-methoxy-1-methyl-1H-quinolin-2-one

3-((R)-2-Hydroxy-3-methyl-butyl)-4,8-dimethoxy-1H-quinolin-2-one

methyl iodide

Refernces

• 1、 Barr,Boyd,Sharma,Evans,Malone,Mehta. "Resolution of prenyl bromohydrin esters and derivatives: Synthesis of the quinoline alkaloid (+)-(R)- and (-)-(S)-lunacridine". . p. 11219 - 11234. Retrieved 2007/10/02.