4,5,6,9-Tetramethoxyindeno[1,2,3-ij]isoquinoline

Base Information

• Chemical Name: 4,5,6,9-Tetramethoxyindeno[1,2,3-ij]isoquinoline
• CAS No.: 38366-04-0
• Molecular Formula: C₁₉H₁₇NO₄
• Molecular Weight: 323.348
• Mol file: 38366-04-0.mol

Synonyms:Rufescin;Rufescine

Chemical Property of 4,5,6,9-Tetramethoxyindeno[1,2,3-ij]isoquinoline

Chemical Property:

• PSA: 49.81000
• LogP: 3.91660

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: An isoquinoline alkaloid, rufescine has been isolated from the stems of A buta rufescens and also occurs in the aerial portions of A . imene. The structure given has been assigned on the basis of chemical and spectroscopic data.

Technology Process of 4,5,6,9-Tetramethoxyindeno[1,2,3-ij]isoquinoline

There total 7 articles about 4,5,6,9-Tetramethoxyindeno[1,2,3-ij]isoquinoline 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%

C22H25NO6 (1453498-46-8) → rufescine (38366-04-0)

Guidance literature:

With oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 40 ℃; for 8h; Inert atmosphere;

DOI:10.1002/ejoc.201201190

Reference yield:

4,5,6,9-Tetramethoxy-indeno[1,2,3-ij]isoquinoline-8-carboxylic acid (91586-02-6) → rufescine (38366-04-0)

Guidance literature:

With (C₆F₅Cu)2*dioxane; In quinoline; at 225 ℃; for 0.416667h; Yield given;

DOI:10.1021/jo00195a035

Reference yield:

methyl 4,5,6,9-tetramethoxyindeno<1,2,3-ij>isoquinoline-8-carboxylate (91586-01-5) → rufescine (38366-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1: LiOH*H₂O / tetrahydrofuran; H₂O / 16 h / 80 °C

2: (C₆F₅Cu)2*dioxane / quinoline / 0.42 h / 225 °C

With lithium hydroxide; (C₆F₅Cu)2*dioxane; In tetrahydrofuran; quinoline; water;

DOI:10.1021/jo00195a035

upstream raw materials:

4,5,6,9-Tetramethoxy-indeno[1,2,3-ij]isoquinoline-8-carboxylic acid

methyl 4,5,6,9-tetramethoxyindeno<1,2,3-ij>isoquinoline-8-carboxylate

2-bromo-5-methoxy-benzaldehyde

ethyl (2,3,4-trimethoxyphenethyl)carbamate

Refernces

• 1、 Boger, Dale L.,Brotherton, Christine E.. "Total Syntheses of Azafluoranthene Alkaloids: Rufescine and Imeluteine". . p. 4050 - 4055. Retrieved 2007/10/02.