Citrusinine I

Base Information

• Chemical Name: Citrusinine I
• CAS No.: 86680-32-2
• Molecular Formula: C16H15 N O5
• Molecular Weight: 301.299
• DSSTox Substance ID: DTXSID10235760
• Nikkaji Number: J727.343F
• Wikidata: Q83117648
• Pharos Ligand ID: 2LVXKH3J4PBP
• Metabolomics Workbench ID: 44355
• ChEMBL ID: CHEMBL451705
• Mol file: 86680-32-2.mol

Synonyms:citrusinine I;citrusinine-I

Chemical Property of Citrusinine I

Chemical Property:

• Vapor Pressure: 1.75E-13mmHg at 25°C
• Melting Point: 205-208 °C
• Boiling Point: 567.5°C at 760 mmHg
• PKA: 7.51±0.20(Predicted)
• Flash Point: 297°C
• PSA: 80.92000
• Density: 1.378g/cm³
• LogP: 2.12010
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 301.09502258
• Heavy Atom Count: 22
• Complexity: 431

Purity/Quality:

99% ^*data from raw suppliers

CITRUSININE I 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C=CC=C2O)C(=O)C3=C1C(=C(C=C3O)OC)OC

Technology Process of Citrusinine I

There total 13 articles about Citrusinine I 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%

5-benzyloxy-1-hydroxy-3,4-dimethoxy-10-methyl-9(10H)-acridone (149220-86-0) → Citrusinine-I (86680-32-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; acetone; at 50 ℃; for 1h;

DOI:10.1248/cpb.41.445

Reference yield: 20.0%

5-benzyloxy-1,3,4-trimethoxy-10-methyl-9(10H)-acridone (130897-43-7) → 5-hydroxy-1,3,4-trimethoxy-10-methyl-9(10H)-acridone (130897-45-9) + Citrusinine-I (86680-32-2) + 5-benzyloxy-1-hydroxy-3,4-dimethoxy-10-methyl-9(10H)-acridone (149220-86-0)

Guidance literature:

With hydrogenchloride; In ethanol; for 4h; Heating;

DOI:10.1248/cpb.41.445

Reference yield:

asaronic acid (490-64-2) → Citrusinine-I (86680-32-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 4 N aq. NaOH / benzene; CH₂Cl₂; H₂O / 1 h / Ambient temperature

2: 1.) sec-BuLi, TMEDA, 2.) I₂ / 1.) hexane, THF, -78 deg C, 1 h, 2.) hexane, THF, -20 deg C, 10 min

3: 81 percent / K₂CO₃, CuCl / propan-2-ol / 1.5 h / Heating

4: 69 percent / K₂CO₃ / dimethylformamide / 3 h / 20 - 45 °C

5: 1.) POCl₃, 2.) 1 N aq. HCl / 1.) reflux, 30 min, 2.) EtOH, reflux, 1 h

6: 78 percent / KOH / dimethylsulfoxide / 1 h / Ambient temperature

7: 20 percent / 6 N aq. HCl / ethanol / 4 h / Heating

With hydrogenchloride; potassium hydroxide; sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; iodine; sec.-butyllithium; potassium carbonate; copper(l) chloride; trichlorophosphate; In ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; isopropyl alcohol; benzene;

DOI:10.1248/cpb.41.445

upstream raw materials:

5-benzyloxy-1,3,4-trimethoxy-10-methyl-9(10H)-acridone

5-benzyloxy-1-hydroxy-3,4-dimethoxy-10-methyl-9(10H)-acridone

asaronic acid

1-bromo-2,3,5-trimethoxybenzene

Downstream raw materials:

1-Hydroxy-3,4,5-trimethoxy-10-methyl-10H-acridin-9-one

Refernces