7257-25-2

Basic information

• Product Name: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one
• Synonyms: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one;7,8,9,10-Tetrahydro-5H-cyclohepta[b]indol-6-one
• CAS NO: 7257-25-2
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 199.24842
• Mol File: 7257-25-2.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one(7257-25-2)
• EPA Substance Registry System: 7,8,9,10-tetrahydrocyclohepta[b]indol-6(5H)-one(7257-25-2)

Safety Data

• Hazardous Substances Data: 7257-25-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 35, p. 4700, 1987 DOI: 10.1248/cpb.35.4700

Upstream product

• 2047-89-4 5,6,7,8,9,10-hexahydrocyclohept[b]indole 
• 56382-69-5 cycloheptanone p-tolylsulfonylhydrazone 
• 287944-13-2 2-(cyclohept-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 835882-35-4 (Z)-cyclohept-1-en-1-ylboronic acid 
• 100-63-0 phenylhydrazine 
• 3008-39-7 cycloheptane-1,2-dione 
• 62-53-3 aniline 
• 105553-58-0 2-(phenylamino)cyclohept-2-enone 
• 934-20-3 2-(hydroxymethylene)cycloheptanone 
• 502-42-1 cycloheptanone 
• 64-18-6 formic acid 
• 14192-58-6 2-[(2-phenylhydrazino)methylidene]cycloheptanone 
• 52851-01-1 methyl 1H-indole-2-pentanoic acid 
• 64799-08-2 2-formylcycloheptanone 

Downstream Products

• 1356957-89-5 1-phenyl-4,5,6,11-tetrahydropyrazolo[4',3':6,7]cyclohepta[b]indole 
• 1357598-38-9 6-phenyl-7,8,9,14-tetrahydroquinolino[2',3':7,6]cyclohept[1,2-b]indole 
• 1262726-91-9 4-chloro-6-phenyl-7,8,9,14-tetrahydroquinolino[2',3':7,6]cyclohept[b]indole 

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.

Synthesis of substituted tetrahydron-1H-carbazol-1-one and analogs via PhI(OCOCF3)2-mediated oxidative C-C bond formation

A variety of tetrahydro-1H-carbazol-1-ones and analogs were conveniently synthesized from the reaction of the corresponding 2-(phenylamino)cyclohex-2- enone with hypervalent iodine reagent PhI(OCOCF3)2 (PIFA), through a direct intramolecular oxidative C(sp2)-C(sp2) bond formation. This approach realized the construction of the biologically important tetrahydro-1H-carbazol-1-one and tetrahydrocyclohepta[b]indol-6(5H)- one skeletons. The mechanism of the process was proposed and briefly discussed.

A back-to-front fragment-based drug design search strategy targeting the DFG-out pocket of protein tyrosine kinases

We present a straightforward process for the discovery of novel back pocket-binding fragment molecules against protein tyrosine kinases. The approach begins by screening against the nonphosphorylated target kinase with subsequent counterscreening of hits against the phosphorylated enzyme. Back pocket-binding fragments are inactive against the phosphorylated kinase. Fragment molecules are of insufficient size to span both regions of the ATP binding pocket; thus, the outcome is binary (back pocket-binding or hinge-binding). Next, fragments with the appropriate binding profile are assayed in combination with a known hinge-binding fragment and subsequently with a known back pocket-binding fragment. Confirmation of back pocket-binding by Yonetani-Theorell plot analysis progresses candidate fragments to crystallization trials. The method is exemplified by a fragment screening campaign against vascular endothelial growth factor receptor 2, and a novel back pocket-binding fragment is presented.