1-hydroxy-3,6-dimethoxy-1,2-dimethyl-9H-carbazol-4-one

Base Information

• Chemical Name: 1-hydroxy-3,6-dimethoxy-1,2-dimethyl-9H-carbazol-4-one
• CAS No.: 115920-42-8
• Molecular Formula: C₁₆H₁₇NO₄
• Molecular Weight: 287.315
• DSSTox Substance ID: DTXSID80921865
• Nikkaji Number: J936.805A
• Wikidata: Q82895004
• Mol file: 115920-42-8.mol

Synonyms:carbazomycin H

Chemical Property of 1-hydroxy-3,6-dimethoxy-1,2-dimethyl-9H-carbazol-4-one

Chemical Property:

• Vapor Pressure: 8.32E-13mmHg at 25°C
• Boiling Point: 547.2°C at 760 mmHg
• Flash Point: 284.7°C
• PSA: 71.55000
• Density: 1.33g/cm³
• LogP: 2.50070
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 287.11575802
• Heavy Atom Count: 21
• Complexity: 489

Purity/Quality:

CARBAZOMYCIN H 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=O)C2=C(C1(C)O)NC3=C2C=C(C=C3)OC)OC

Technology Process of 1-hydroxy-3,6-dimethoxy-1,2-dimethyl-9H-carbazol-4-one

There total 12 articles about 1-hydroxy-3,6-dimethoxy-1,2-dimethyl-9H-carbazol-4-one 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: 42.0%

methyllithium (917-54-4) + 3,6-dimethoxy-2-methyl-9H-carbazole-1,4-quinone (192188-92-4) → 1,4-dihydro-1-hydroxy-3,6-dimethoxy-1,2-dimethyl-9H-carbazol-4-one (115920-42-8) + 6-methoxy-2,3-dimethyl-9H-carbazole-1,4-quinone

Guidance literature:

In tetrahydrofuran; at -78 ℃; for 6h; Further Variations:; Temperatures; reaction times, molar ratios; Product distribution;

DOI:10.1002/ejoc.200390116

Reference yield: 41.0%

methyllithium (917-54-4) + 3,6-dimethoxy-2-methyl-9H-carbazole-1,4-quinone (192188-92-4) → 1,4-dihydro-1-hydroxy-3,6-dimethoxy-1,2-dimethyl-9H-carbazol-4-one (115920-42-8)

Guidance literature:

In tetrahydrofuran; at -78 - 25 ℃;

DOI:10.1016/S0040-4039(97)00826-5

Reference yield:

acetic acid 2,4-dimethoxy-3-methyl-phenyl ester (96502-90-8) → 1,4-dihydro-1-hydroxy-3,6-dimethoxy-1,2-dimethyl-9H-carbazol-4-one (115920-42-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / aq. KOH / ethanol / 1 h / 25 °C

2: 90 percent / (NH₄)2Ce(NO₃)6 / acetonitrile; H₂O / 0.5 h / 0 °C

3: 83 percent / methanol / 1 h / 25 °C

4: 73 percent / Cu(OAc)2 / Pd(OAc)2 / acetic acid / 19 h / 117 °C

5: 41 percent / tetrahydrofuran / -78 - 25 °C

With potassium hydroxide; copper diacetate; ammonium cerium(IV) nitrate; palladium diacetate; In tetrahydrofuran; methanol; ethanol; water; acetic acid; acetonitrile;

upstream raw materials:

methyllithium

3,6-dimethoxy-2-methyl-9H-carbazole-1,4-quinone

2-methoxy-3-methyl-1,4-benzoquinone

2,4-dimethoxy-3-methylphenol

Refernces

• 1、 Knoelker, Hans-Joachim,Froehner, Wolfgang. "Palladium-catalyzed total synthesis of the antibiotic carbazole alkaloids carbazomycin G and H". . p. 173 - 175. Retrieved 2007/10/03.