Trilobine

Base Information

• Chemical Name: Trilobine
• CAS No.: 6138-73-4
• Molecular Formula: C35H34 N2 O5
• Molecular Weight: 562.665
• UNII: 6H8V6C2Q77
• DSSTox Substance ID: DTXSID90976922
• Nikkaji Number: J8.347J
• Wikidata: Q27108483
• ChEMBL ID: CHEMBL500324
• Mol file: 6138-73-4.mol

Synonyms:trilobine;trilobine sulfate

Chemical Property of Trilobine

Chemical Property:

• Melting Point: 237°
• PSA: 61.42000
• Density: 1.242g/cm3
• LogP: 7.17540
• XLogP3: 5.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 562.24677219
• Heavy Atom Count: 42
• Complexity: 929

Purity/Quality:

TRILOBINE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCC2=CC3=C4C=C2C1CC5=CC(=C(C=C5)OC)OC6=CC=C(CC7C8=C(O4)C(=C(C=C8CCN7)OC)O3)C=C6
• Isomeric SMILES: CN1CCC2=CC3=C4C=C2[C@@H]1CC5=CC(=C(C=C5)OC)OC6=CC=C(C[C@H]7C8=C(O4)C(=C(C=C8CCN7)OC)O3)C=C6
• Description: A bisbenzylisoquinoline alkaloid, this base has been isolated from Cocculus sarmentosus Diels and C. trilobus DC. It crystallizes as colourless prisms and is dextrorotatory with [α]29D + 296.3° (CHCI3). Both the hydrochloride and hydro_x0002_bromide are crystalline and sparingly soluble in H20 and the dimethiodide has m.p. 273°C (dec.). Two methoxyl groups and two methylimino groups are present. With dimethyl sulphate in NaOH, the base yields trilobinemethylmethine as long, colourless prisms, m.p. 106° C which is optically inactive and on ozonization furnishes 2-methoxy-5:4'-dialdehydodiphenyl ether, m.p. 72-5°C and a complex dialdehyde, m.p. 124°C.

Technology Process of Trilobine

There total 9 articles about Trilobine 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: 15.0%

C36H36N2O7 → (+)-isotrilobine (26195-62-0) + nortrilobine + (+)-O-methyl cocsoline (54352-71-5) + trilobine (6138-73-4)

Guidance literature:

With ferrous(II) sulfate heptahydrate; In methanol; at 20 ℃; for 48h; Cooling with ice;

Reference yield:

2-benzoyl-6,7,6',12'-tetramethoxy-oxyacanth-1'-ene (61897-94-7) → trilobine (6138-73-4)

Guidance literature:

Multi-step reaction with 4 steps

1: NaBH₄

2: LiAlH₄, AlCl₃

3: (i) BBr₃, CH₂Cl₂, (ii) aq. HBr, (iii) /BRN= 102415/

4: H₂ / Pd-C

With sodium tetrahydroborate; lithium aluminium tetrahydride; aluminium trichloride; hydrogen; palladium on activated charcoal;

DOI:10.1016/S0040-4039(01)85520-9

Reference yield:

2-benzoyl-6,7,6',12'-tetramethoxy-1',17'-seco-oxyacanthan-1'-one (61897-93-6) → trilobine (6138-73-4)

Guidance literature:

Multi-step reaction with 5 steps

1: POCl₃

2: NaBH₄

3: LiAlH₄, AlCl₃

4: (i) BBr₃, CH₂Cl₂, (ii) aq. HBr, (iii) /BRN= 102415/

5: H₂ / Pd-C

With sodium tetrahydroborate; lithium aluminium tetrahydride; aluminium trichloride; hydrogen; trichlorophosphate; palladium on activated charcoal;

DOI:10.1016/S0040-4039(01)85520-9

upstream raw materials:

2-benzyl-7,6'-epoxy-6,12'-dimethoxy-2'-methyl-(1'αH)-oxyacanthane

(S)-7²-benzoyl-3⁴,7^{6,7_,92_{-tetramethoxy-7}1,2,3,4}-tetrahydro-4,8-dioxa-12-aza-3(1,3),5,9(1,4)-tribenzena-7(1,8)-isoquinolina-tridecaphanedioic acid 13-tert-butyl ester 1-methyl ester

2-benzyl-6,7,6',12'-tetramethoxy-2'-methyl-(1'αH)-oxyacanthane

2-benzoyl-6,7,6',12'-tetramethoxy-oxyacanth-1'-ene

Downstream raw materials:

(+)-isotrilobine

aristelegin-C

Refernces

• 1、 Inubushi,Ito,Masaki,Ibuka. "Synthesis of trilobine, isotrilobine, and obaberine". . p. 1636 - 1644. Retrieved 2007/10/04.