297763-74-7

Basic information

• Product Name: 6-(Trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one
• Synonyms: 6-(trifluoromethyl)-3,4-dihydro-2H-carbazol-1(9H)-one;6-(Trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one
• CAS NO: 297763-74-7
• Molecular Formula: C₁₃H₁₀F₃NO
• Molecular Weight: 253.22
• Mol File: 297763-74-7.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 384.7 °C at 760 mmHg
• Flash Point: 186.5 °C
• Appearance: /
• Density: 1.416
• CAS DataBase Reference: 6-(Trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(Trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one(297763-74-7)
• EPA Substance Registry System: 6-(Trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one(297763-74-7)

Safety Data

• Hazardous Substances Data: 297763-74-7(Hazardous Substances Data)

Upstream product

• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 141091-37-4 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 89490-05-1 cyclohex-1-enylboronic acid 
• 368-90-1 4-(trifluoromethyl)phenylhydrazine 
• 1176326-20-7 C₁₃H₁₃F₃N₂O 
• 455-14-1 4-trifluoromethylphenylamine 
• 39695-64-2 2-(hydroxymethylene)cyclohexanone 
• 2923-56-0 4-(trifluoromethyl)phenylhydrazine hydrochloride 
• 765-87-7 cyclohexane-1,2-dione 

Relevant articles and documents

Copper-catalyzed tri- or tetrafunctionalization of alkenylboronic acids to prepare tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles

We describe a cascade strategy for tri- or tetrafunctionalization of alkenylboronic acids to prepare diverse tetrahydrocarbazol-1-ones and indolo[2,3-a]carbazoles in good yields withN-hydroxybenzotriazin-4-one (HOOBT) and arylhydrazines as oxygen and nitrogen sources, respectively. Mechanistic studies reveal that the domino reaction undergoes the copper-catalyzed Chan-Lam reaction, [2,3]-rearrangement, nucleophilic substitution, oxidation and sequential [3,3]-rearrangement over five steps in a one-pot reaction. The reaction shows a broad substrate scope and tolerates a wide range of functional groups. More importantly, the reaction is easily performed at gram scales and the product is purified by simple extraction, washing, and recrystallization without flash column chromatography. The present protocol features easily available starting materials, high site-marked functionalization, five-step cascade in one pot, multiple C-C/C-O/C-N bond formation, and diversity of indole motifs.

Design, synthesis and evaluation of hybrid of tetrahydrocarbazole with 2,4-diaminopyrimidine scaffold as antibacterial agents

Several 6-substituted tetrahydrocarbazole derivatives were designed, synthesized and evaluated for the antibacterial activities against Staphylococcus aureus Newman strain. Subsequently, 2,4-diaminopyrimidine scaffold was merged with the tetrahydrocarbazole unit to generate a series of novel hybrid derivatives and the antibacterial activities were also investigated. Among these novel hybrids, compound 12c showed the most potent activity with a MIC of 0.39–0.78 μg/mL against S. aureus Newman and Escherichia coli AB1157 strain. In addition, compound 12c exhibited low MIC values against a panel of multidrug-resistant strains of S. aureus.

Substituted tetrahydrocarbazoles with potent activity against human papillomaviruses

The synthesis and SAR of a series of substituted 1-aminotetrahydrocarbazoles with potent activity against human papillomaviruses are described. Synthetic approaches allowing for variation of the substitution pattern of the tetrahydrocarbazole are outlined and resulting changes in antiviral activity are highlighted. Several compounds with in vitro antiviral activity (W12 antiviral assay) in the low nanomolar range were identified and (1R)-6-bromo-N-[(1R)-1-phenylethyl]-2,3,4,9-tetrahydro-1H-carbazole-1-amine was selected for further evaluation.