Imerubrine

Base Information

• Chemical Name: Imerubrine
• CAS No.: 58189-33-6
• Molecular Formula: C₂₀H₁₇NO₅
• Molecular Weight: 351.359
• DSSTox Substance ID: DTXSID30206912
• Nikkaji Number: J14.660I
• Wikidata: Q83080786
• Mol file: 58189-33-6.mol

Synonyms:imerubrine

Chemical Property of Imerubrine

Chemical Property:

• Vapor Pressure: 9.79E-18mmHg at 25°C
• Boiling Point: 668.5°Cat760mmHg
• Flash Point: 358.1°C
• PSA: 66.88000
• Density: 1.36g/cm³
• LogP: 3.27680
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 351.11067264
• Heavy Atom Count: 26
• Complexity: 682

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C2C(=CC1=O)C3=NC=CC4=C3C2=C(C(=C4OC)OC)OC
• Description: A further alkaloid obtained from the stems of Abuta imene and A. rufescens, this base has been shown to possess the structure given above.

Technology Process of Imerubrine

There total 17 articles about Imerubrine 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%

16-aza-5-methoxy-10,11,12-trimethoxy-18-oxapentacyclo[7.7.1.12,6.02,8.013,17]octadeca-1(16),7,9(10),11,13(17),14-hexaen-4-one → imerubrine (58189-33-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja0101072

Reference yield: 70.0%

6b,7,8,9-tetrahydro-4,5,6,8,8-pentamethoxyindeno<1,2,3-ij>cyclopropa<1,2-c>isoquinolin-9(9H)-one (191414-83-2) → imerubrine (58189-33-6)

Guidance literature:

With trifluoroacetic acid; In chloroform; at 18 ℃; for 2h;

DOI:10.1039/c39940000591

Reference yield: 35.0%

grandirubrine (74631-22-4) + diazomethyl-trimethyl-silane (18107-18-1) → imerubrine (58189-33-6) + isoimerubrine (74684-11-0)

Guidance literature:

In tetrahydrofuran; methanol; hexane; at 25 ℃; for 20h;

DOI:10.1021/ja00155a009

upstream raw materials:

diazomethane

grandirubrine

6b,7,8,9-tetrahydro-4,5,6,8,8-pentamethoxyindeno<1,2,3-ij>cyclopropa<1,2-c>isoquinolin-9(9H)-one

grandirubrine

Refernces

• 1、 Banwell, Martin G.,Ireland, Neil K.. "Regiocontrolled Total Synthesis of Imerubrine - the First Total Synthesis of a Tropoloisoquinoline Alkaloid". . p. 591 - 592. Retrieved 1994.
• 2、 Boger, Dale L.,Takahashi, Kanji. "Total synthesis of granditropone, grandirubrine, imerubrine, and isoimerubrine". . p. 12452 - 12459. Retrieved 2007/10/03.