Quinocarcin

Base Information

• Chemical Name: Quinocarcin
• CAS No.: 84573-33-1
• Molecular Formula: C₁₈H₂₂N₂O₄
• Molecular Weight: 330.384
• DSSTox Substance ID: DTXSID501004854
• Wikidata: Q83000070
• Metabolomics Workbench ID: 99152
• ChEMBL ID: CHEMBL508248
• Mol file: 84573-33-1.mol

Synonyms:D 52;D-52;isoquinocarcin;KW 2152;KW-2152;quinocarcin;quinocarmycin;quinocarmycin citrate

Chemical Property of Quinocarcin

Chemical Property:

• Vapor Pressure: 1.08E-11mmHg at 25°C
• Boiling Point: 521.3°Cat760mmHg
• Flash Point: 269.1°C
• PSA: 62.24000
• Density: 1.41g/cm³
• LogP: 0.98220
• XLogP3: -1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 330.15795719
• Heavy Atom Count: 24
• Complexity: 543

Purity/Quality:

95% ^*data from raw suppliers

(-)-Quinocarcin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2CC(C1C3CC4=C(C5N3C2OC5)C(=CC=C4)OC)C(=O)O
• Isomeric SMILES: CN1[C@H]2C[C@H]([C@@H]1[C@@H]3CC4=C([C@H]5N3[C@@H]2OC5)C(=CC=C4)OC)C(=O)O
• Uses: (-)-Quinocarcin are potent antitumor antibiotics that plays a key role in the construction of tetracyclic THIQ-pyrrolidine core scaffold.

Technology Process of Quinocarcin

There total 110 articles about Quinocarcin 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: 94.0%

<5R-(5α,7β,8β,10β,11β,11aβ)>-7-cyano-5,7,8,9,10,11,11a,12-octahydro-4-methoxy-5-(hydroxymethyl)-13-methyl-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid (96251-59-1) → (-)-quinocarcin (84573-33-1)

Guidance literature:

With silver nitrate; In methanol; water; for 4h; Ambient temperature;

DOI:10.1021/ja00076a036

Reference yield: 89.0%

4-cyano-6-hydroxymethyl-3,12-imino-7-methoxy-13-methyl-1,2,3,4,6,11,11a,12-octahydroazepino<1,2-b>isoquinoline-1-carboxylic acid (96251-59-1,115361-93-8) → (-)-quinocarcin (84573-33-1)

Guidance literature:

With silver nitrate; In methanol; water;

DOI:10.1021/ja00033a089

Reference yield: 87.0%

(-)-quinocarcinamide formate (1030029-43-6) → (-)-quinocarcin (84573-33-1)

Guidance literature:

(-)-quinocarcinamide formate; With ammonia; lithium; In tetrahydrofuran; at -25 ℃; for 0.25h;

With hydrogenchloride; In methanol; water; at 20 ℃; for 2h; pH=6; Further stages.;

DOI:10.1021/ja800662q

upstream raw materials:

4-cyano-6-hydroxymethyl-3,12-imino-7-methoxy-13-methyl-1,2,3,4,6,11,11a,12-octahydroazepino<1,2-b>isoquinoline-1-carboxylic acid

7-cyanoquinocarcinol

<5R-(5α,7β,8β,10β,11β,11aβ)>-7-cyano-5,7,8,9,10,11,11a,12-octahydro-4-methoxy-5-(hydroxymethyl)-13-methyl-8,11-iminoazepino<1,2-b>isoquinoline-10-carboxylic acid

2-bromo-3-methylanisole

Downstream raw materials:

4-cyano-6-hydroxymethyl-3,12-imino-7-methoxy-13-methyl-1,2,3,4,6,11,11a,12-octahydroazepino<1,2-b>isoquinoline-1-carboxylic acid