57152-69-9

Usage

Chemical class

Ester

Derived from

1H-Indol-3-ol (indole compound)

Functional groups

Phenyl group, benzoate moiety

Versatile building block

For the synthesis of various organic molecules

Potential applications

Pharmaceutical and chemical industries, drug compounds, agrochemicals

Usage as fragrance and flavoring agents

Due to pleasant odor

Upstream product

• 1859-39-8 2-phenyl-N-hydroxyindole 
• 98-88-4 benzoyl chloride 
• 58810-39-2 2-phenyl-1H-indol-1-yl benzoate 
• 2989-63-1 2-phenyl-3H-indol-3-one 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

N-Heterocyclic Carbene-Catalyzed Formal Conjugate Hydroacylation: An Atom-Economic Synthesis of 1 H-Indol-3-yl Esters

An atom-economic synthesis of useful 1H-indol-3-yl esters has been demonstrated by an N-heterocyclic carbene (NHC)-catalyzed formal conjugate hydroacylation of 2-phenyl-indol-3-ones with readily accessible aldehydes. This reaction involves a reductive hydride transfer process that was rarely investigated in the field of NHC catalysis. In this process, the hydrogen from the aldehydes was formally transferred to a heteroatom with NHC catalysis for the first time.

STUDIES ON TERTIARY AMINE OXIDES. LXXII. SOME NUCLEOPHILIC REACTIONS OF 1-HYDROXY-2-PHENYLINDOLE

1-Hydroxy-2-phenylindole (1) reacts with tosyl chloride and p-nitrobenzenesulfonyl chloride in DMF-pyridine to give the corresponding 2-phenyl-3-sulfonyloxyindole (2 and 4).Benzoyl chloride is less reactive, and 1-benzoyloxy-2-phenylindole (5) or 3-benzoyloxy-2-phenylindole (6) is formed, depending upon the reaction conditions. 3-Acetoxy-2-phenylindole (7) is also obtained by refluxing 1 with acetic anhydride or with acetyl chloride in DMF-pyridine.Treatment of 1 with tosyl chloride and then with 1-morpholinocyclohexene (9), ethyl acetoacetate (17) and ethyl cyanoacetate (20) in DMF-pyridine at room temperature affords 3-(2-oxocyclohexyl)-2-phenylindole (10), ethyl α-(2-phenyl-3-indolyl)acetoacetate (18) and ethyl α-(2-phenyl-3-indolyl)cyanoacetate (21) in 23.2, 41 and 61percent yields, respectively.Keywords: enehydroxylamine system; 1-acyloxy-2-phenylindole; 3-acyloxy-2-phenylindole; 1-morpholinocyclohexene; 3-(2-oxocyclohexyl)-2-phenylindole; ethyl α-(2-phenyl-3-indolyl)acetoacetate; ethyl α-(2-phenyl-3-indolyl)cyanoacetate