Worenine

Base Information

• Chemical Name: Worenine
• CAS No.: 38763-29-0
• Molecular Formula: C20H16NO4
• Molecular Weight: 334.3448
• UNII: STF4A6F4EH
• Nikkaji Number: J490.580F
• Wikidata: Q27151413
• Mol file: 38763-29-0.mol

Synonyms:worenine

Chemical Property of Worenine

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 40.80000
• Density: g/cm³
• LogP: 3.11620
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 334.10793299
• Heavy Atom Count: 25
• Complexity: 530

Purity/Quality:

98%,99%, ^*data from raw suppliers

Worenine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C3=CC4=C(C=C3CC[N+]2=CC5=CC6=C(C=C15)OCO6)OCO4
• Description: This quaternary alkaloid is present in Cop tis japonica and has been isolated as the tetrahydro base, colourless prisms from EtOH with m.p. 2l2-3°C, oxidized by iodine in EtOH to worenine iodide. The latter forms yellow crystals from which the corresponding chloride may be obtained in the form of orange-yellow prisms, m.p. 295°C (dec.).
• Uses: Worenine is used in the a flurophore switched probe which aids in correction of an abasic site (AP site) caused by the removal of a damaged base in DNA

Technology Process of Worenine

There total 6 articles about Worenine 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: 95.0%

tetrahydroworenine (38763-50-7,38763-53-0,38899-70-6,65391-28-8,65391-29-9) → C20H16NO4(1+) (38763-29-0)

Guidance literature:

With iodine; potassium acetate; In ethanol; at 20 ℃; Inert atmosphere;

DOI:10.1002/chem.201601245

Reference yield: 63.0%

C20H17NO4 → C20H16NO4(1+) (38763-29-0)

Guidance literature:

With rhodium(III) chloride trihydrate; oxygen; In ethanol; at 80 ℃; for 8h;

DOI:10.1002/chem.201601245

Reference yield:

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline (94143-83-6) → C20H16NO4(1+) (38763-29-0)

Guidance literature:

Multi-step reaction with 4 steps

1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve

2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere

3: sodium formate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere

4: rhodium(III) chloride trihydrate; oxygen / ethanol / 8 h / 80 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; rhodium(III) chloride trihydrate; oxygen; sodium formate; potassium carbonate; benzoic acid; In methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/chem.201601245

upstream raw materials:

5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline

6-bromo-3,4-methylenedioxybenzaldehyde

tetrahydroworenine

Refernces