Verruculotoxin

Base Information

• Chemical Name: Verruculotoxin
• CAS No.: 56092-63-8
• Molecular Formula: C15H20 N2 O
• Molecular Weight: 244.33
• DSSTox Substance ID: DTXSID70204639
• Nikkaji Number: J11.116C
• Wikidata: Q27108540
• Mol file: 56092-63-8.mol

Synonyms:1-oxo-3-benzyloctahydro-2H-pyrido(1,2-a)pyrazine;verruculotoxin

Chemical Property of Verruculotoxin

Chemical Property:

• Vapor Pressure: 8.13E-08mmHg at 25°C
• Boiling Point: 436.4°Cat760mmHg
• Flash Point: 217.7°C
• PSA: 35.83000
• Density: 1.14g/cm³
• LogP: 1.79580
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 244.157563266
• Heavy Atom Count: 18
• Complexity: 299

Purity/Quality:

VERRUCULOTOXIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCN2CC(NC(=O)C2C1)CC3=CC=CC=C3
• Isomeric SMILES: C1CCN2C[C@@H](NC(=O)[C@@H]2C1)CC3=CC=CC=C3

Technology Process of Verruculotoxin

There total 11 articles about Verruculotoxin 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: 76.0%

(3S,9aS)-3-Benzyl-2-(toluene-4-sulfonyl)-hexahydro-pyrido[1,2-a]pyrazin-1-one (134746-10-4) → verruculotoxin (56092-63-8)

Guidance literature:

With naphthalene radical anion sodium salt; In 1,2-dimethoxyethane; at 0 - 20 ℃; for 6h;

DOI:10.1016/0040-4039(91)80345-7

Reference yield: 25.0%

(3S,6S)-3-Benzyl-1,4-diaza-5-methoxybicyclo<4.4.0>dec-4-ene (122571-27-1) → verruculotoxin (56092-63-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; water; at 25 ℃; for 95h;

DOI:10.1055/s-1988-27767

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → verruculotoxin (56092-63-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / DCC, Et₃N / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 25 deg C, 23 h

2: 1.) H₂, 2.) Et₃N / 1.) 10percent Pd/C / 1.) CH₃OH, 1 atm, 25 deg C, 3 h, 2.) 25 deg C, 16 h

3: 84 percent / CH₂Cl₂ / 50 h / 25 °C

4: 63 percent / BH₃*THF / tetrahydrofuran / 2 h / Heating

5: 25 percent / TsOH / CH₂Cl₂; H₂O / 95 h / 25 °C

With borane-THF; hydrogen; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;

DOI:10.1055/s-1988-27767

upstream raw materials:

(3S,9aS)-3-Benzyl-2-(toluene-4-sulfonyl)-hexahydro-pyrido[1,2-a]pyrazin-1-one

(3S,6S)-3-Benzyl-1,4-diaza-5-methoxybicyclo<4.4.0>dec-4-ene

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

N-benzyloxycarbonyl D/L-pipecolinic acid

Refernces

• 1、 Martens, Juergen,Scheunemann, Matthias. "EPC-synthese von verruculotoxin". . p. 1417 - 1418. Retrieved 2007/10/02.