13815-69-5

Usage

Structure

Carbazole ring with a methyl group at the 4a position and an ethanone functional group at the 11 position

Molecular Weight

267.36 g/mol

Functional Groups

Carbazole ring, ethanone (ketones), and methyl group

Derivative

Carbazole, a heterocyclic aromatic organic compound

Applications

Synthesis of pharmaceuticals, agrochemicals, and other organic compounds

Potential Properties

Biological and pharmacological properties due to its structural features

Research Interest

Subject of interest for further research and development

Complexity

Complex structure with multiple fused rings and functional groups

Solubility

Likely soluble in organic solvents such as ethanol, methanol, or acetone (based on similar compounds)

Stability

May be sensitive to light, heat, or moisture (based on similar compounds)

Reactivity

Could potentially react with nucleophiles, reducing agents, or other reactive species (based on the presence of a ketone group)

InChI:InChI=1/C14H15NO/c1-10(16)15-13-8-4-2-6-11(13)12-7-3-5-9-14(12)15/h2,4,6,8H,3,5,7,9H2,1H3

Upstream product

• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 557086-54-1 1-(9-acetyl-2,3,4,9-tetrahydro-carbazol-4a-yl)-4-methyl-[1,2,4]triazolidine-3,5-dione 
• 13815-65-1 acetic acid-(cyclohexylidene-phenyl-hydrazide) 
• 7664-93-9 sulfuric acid 

Downstream Products

• 23592-74-7 2-acetylcarbazole 
• 89650-63-5 cis-4a-(1-tosyloxyethyl)-9-tosyl-1,2,3,4,4a,9a-hexahydrocarbazole 
• 89650-64-6 cis-4a-ethyl-1,2,3,4,4a,9a-hexahydrocarbazole 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 557086-54-1 1-(9-acetyl-2,3,4,9-tetrahydro-carbazol-4a-yl)-4-methyl-[1,2,4]triazolidine-3,5-dione 
• 142634-90-0 1-Acetylspiro-2'(1')-one 

Relevant academic research and scientific papers

Synthesis of Spiro-Pyrrolidinyloxindoles by Oxidative Rearrangement of N-Acyltetrahydro-β-carbolines Using an Oxone/Aqueous Acetone Mixture

Spiro-pyrrolidinyl-2-oxindoles were prepared by the oxidative rearrangement of Na-acetyl-1,2,3,4-tetrahydro-β-carbolines (THBC) using dimethyldioxirane generated in situ. The Na-acetyl THBC substrates were obtained by Pictet-Spengler and acyl-Pictet-Spengler reactions of L-tryptophan methyl ester, followed by Na-acetylation. The stereoselectivity of the oxidative rearrangement was evaluated and 2D nuclear magnetic resonance (NMR) was used to determine the stereochemistry of the oxindole products relative to L-tryptophan. Density functional theory calculations were consistent with a face selective, substrate controlled, epoxidation of the indolic double bond. The calculations indicated that the resulting epoxide would readily rearrange at room temperature via a concerted ring opening/ring contraction process to give the 3-substituted-2-oxindole.

A Direct Access to 7-Aminoindoles via Iridium-Catalyzed Mild C-H Amidation of N-Pivaloylindoles with Organic Azides

Ir(III)-catalyzed regioselective direct C-7 amidation of indoles in reaction with organic azides has been developed. While its efficiency was varied by the choice of N-directing groups, N-pivaloylindoles were most effective in undergoing the desired amidation at room temperature over a broad range of substrates. The reaction was scalable, and deprotection of the chelation group was also facile.

Direct oxidative coupling of N-acetyl indoles and phenols for the synthesis of benzofuroindolines related to phalarine

Inspired by the biogenetic synthesis of benzofuro-indoline-containing natural products, we designed an oxidative coupling between phenol and N-acetyl indoles. This straightforward and direct radical process, mediated by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and FeCl 3 allowed the regioselective synthesis of benzofuro[3,2-b]indolines, whose structure is found in the natural product phalarine.

Palladium[ii] catalysed C(sp3)-H oxidation of dimethyl carbamoyl tetrahydrocarbazoles

Dimethyl carbamoyl tetrahydrocarbazoles undergo directed oxidation using standard conditions to exclusively provide products from C(sp3)-H oxidation. This result is in contrast to recent studies on the directed C-H olefination of hydrocarbazoles, which result in selective aromatic functionalisation.

Oxaziridine-mediated oxyamination of indoles: An approach to 3-aminoindoles and enantiomerically enriched 3-aminopyrroloindolines

A radical solution: A highly regioselective copper(II)-catalyzed oxyamination of N-acyl indoles with oxaziridines gave aminal products that could be converted in a single step into 3-aminoindoles and 3-aminopyrroloindolines (see scheme). When a chiral N-acyl group was used, the core fragment of some architecturally fascinating pyrroloindoline alkaloids was formed with 91% ee. Bs=benzenesulfonyl, Moc=methoxycarbonyl. Copyright

The first method for protection-deprotection of the indole 2,3-π bond

(Matrix presented) The scope and generality of a new reaction of indoles with MTAD is discussed. In most cases the ene-type reaction proceeds within seconds or minutes at 0°C to provide the urazole adducts in high yield. This reaction provides the first method for protecting the indole 2,3-double bond since the urazole adducts can be reconverted to the starting indole (retro-ene) simply by heating.

Intermolecular Photoreactions of Phthalimide-Alkene Systems. Regio- and Stereoselective Oxetane Formation from N-Methylphthalimide and N-Acetylindole Derivatives

Upon irradiation of N-methylphthalimide (1) in the presence of N-acylindole derivatives (2 or 11), cycloaddition occurred to give sterically hindered oxetanes (5) in moderate yields.Some reactions of these imide-oxetanes, such as formation of benzoxazepines (8 and 12) and eightmembered lactams (9 and 10), are also described.Keywords - intermolecular photoreaction; N-methylphthalimide; N-acylindole; oxetane; cycloaddition; imide-oxetane; benzoxazepine; Paterno-Buchi reaction