N-Methyllaurotetanine

Base Information

• Chemical Name: N-Methyllaurotetanine
• CAS No.: 2169-44-0
• Molecular Formula: C20H23 N O4
• Molecular Weight: 341.407
• Hs Code.: 2933990090
• NSC Number: 247564,247506
• UNII: 11558LRZ50
• DSSTox Substance ID: DTXSID60176073
• Nikkaji Number: J13.790A
• Wikidata: Q27251258
• Pharos Ligand ID: 2THBF3QQBKZY
• Metabolomics Workbench ID: 136471
• ChEMBL ID: CHEMBL464099
• Mol file: 2169-44-0.mol

Synonyms:N-methyllaurotetanine

Chemical Property of N-Methyllaurotetanine

Chemical Property:

• Vapor Pressure: 7.29E-11mmHg at 25°C
• Melting Point: 102.5°C
• Refractive Index: 1.5614 (estimate)
• Boiling Point: 506.1°Cat760mmHg
• Flash Point: 259.9°C
• PSA: 51.16000
• Density: 1.222g/cm³
• LogP: 3.10800
• XLogP3: 3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 341.16270821
• Heavy Atom Count: 25
• Complexity: 475

Purity/Quality:

99%, ^*data from raw suppliers

Lauroscholtzine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC(=C(C3=C2C1CC4=CC(=C(C=C43)OC)O)OC)OC
• Isomeric SMILES: CN1CCC2=CC(=C(C3=C2[C@@H]1CC4=CC(=C(C=C43)OC)O)OC)OC
• Description: This alkaloid, identified as the N-methyl derivative of laurotetanine (q. v.), has been isolated from Escholtzia californica Cham., Phylica fengerialla and P. rogersii Pillans. The base is known in two modifications; as an amorphous powder and a colourless crystals from MeOH containing 0.5 mole of solvent, identical with rogersine (q.v.). The alkaloid has [α]D + 1110 (c 0.86, MeOH) and the ultraviolet spectrum in EtOH has absorption maxima at 219, 282 and 304 rn[J.; while that in alkaline solution (0.05 N/NaOH) has absorption maxima at 223 and 329 mil. The alkaloid yields a crystalline hydriodide, m.p. 245°C; the methiodide, m.p. 199-2000 C and the Q-ethyl (-)-tartrate, m.p. 206-7°C (dec.) giving a methiodide, m.p. 213° C.

Technology Process of N-Methyllaurotetanine

There total 2 articles about N-Methyllaurotetanine 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: 34.0%

(-)-roemerialinone (4684-22-4,28277-75-0,28277-76-1,33458-68-3,33458-69-4) → (+)-1-O-methylisothebaine (95652-98-5) + N-methyllaurotetanine (2169-44-0)

Guidance literature:

In methanol; for 9h; Irradiation;

DOI:10.1016/S0040-4039(00)84405-6

Reference yield: 26.0%

methanol (67-56-1) + boldine (476-70-0) → (+)-Predicentrine (20051-87-0,517-65-7) + N-methyllaurotetanine (2169-44-0) + glaucine (475-81-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/np500893h

Reference yield: 94.0%

4-bromobenzenemethanol (873-75-6) + N-methyllaurotetanine (2169-44-0) → (S)-9-[(4-bromobenzyl)oxy]-1,2,10-trimethoxy-6-methyl-5,6,6a,7-tetrahydro-4H-dibenzo[de,g]quinoline

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/np500893h

upstream raw materials:

(-)-roemerialinone

methanol

boldine

Refernces

• 1、 Gozler,Guinaudeau,Shamma. "The photolysis of proaporphines". . p. 1899 - 1902. Retrieved 2007/10/02.