138469-78-0

Basic information

• Product Name: 1H-Indole, 5-methoxy-3-(phenylmethyl)-
• CAS NO: 138469-78-0
• Molecular Formula: C16H15NO
• Molecular Weight: 237.301
• Mol File: 138469-78-0.mol

Chemical Properties

• CAS DataBase Reference: 1H-Indole, 5-methoxy-3-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole, 5-methoxy-3-(phenylmethyl)-(138469-78-0)
• EPA Substance Registry System: 1H-Indole, 5-methoxy-3-(phenylmethyl)-(138469-78-0)

Safety Data

• Hazardous Substances Data: 138469-78-0(Hazardous Substances Data)

Usage

Type of compound

chemical compound

Indole derivative

yes

Heterocyclic compound

yes

Common sources

plants and animals

Substitution on core structure

5-methoxy, 3-(phenylmethyl)

Unique properties

yes

Potential applications

pharmaceuticals, agrochemicals, organic compounds

Biological activities

may have various

Building block

in the synthesis of compounds

Further research

needed for valuable insights into potential uses and effects

Upstream product

• 101351-10-4 2-(5-methoxy-2-nitrophenyl)-3-phenylpropionitrile 
• 103608-21-5 (5-methoxy-1H-indol-3-yl)(phenyl)methanone 
• 1006-94-6 5-methoxylindole 
• 100-39-0 benzyl bromide 
• 21857-45-4 5-methoxyindoline 
• 100-51-6 benzyl alcohol 
• 100-46-9 benzylamine 
• 124043-85-2 2-(2-amino-5-methoxyphenyl)ethyl alcohol 

Downstream Products

• 1386875-45-1 3-benzyl-5-methoxy-1-methyl-1H-indole 
• 1256844-83-3 (5-methoxy-1-methyl-1H-indol-3-yl)(phenyl)methanone 

Relevant articles and documents

Nickel-catalyzed C3-alkylation of indoles with alcohols: Via a borrowing hydrogen strategy

An efficient method for the Ni-catalyzed C3-alkylation of indoles using readily available alcohols as the alkylating reagents has been developed. The alkylation was addressed with an air and moisture-stable binuclear nickel complex ligated by tetrahydroquinolin-8-one as the effective pre-catalyst. The newly developed transformation could accommodate a broad substrate scope including primary/secondary benzylic and aliphatic alcohols and substituted indoles. Mechanistic studies suggested that the reaction proceeds through a borrowing hydrogen pathway.

Efficient copper-catalyzed synthesis of C3-alkylated indoles from indoles and alcohols

A highly efficient copper(II) catalyst system for alkylation of indoles with alcohols via hydrogen borrowing method has been developed to afford C3-alkylated indoles in good to excellent yields. Cu(OAc)2 in the combination with dppm ligand has been found to be the most suitable catalyst system for this alkylation reaction.

Manganese-Catalyzed Regioselective Dehydrogenative C-versus N-Alkylation Enabled by a Solvent Switch: Experiment and Computation

The first base metal-catalyzed regioselective dehydrogenative alkylation of indolines using readily available alcohols as the alkylating reagent is reported. A single air-and moisture-stable manganese catalyst provides access to either C3-or N-alkylated indoles depending on the solvent used. Mechanistic studies indicate that the reaction takes place through a combined acceptorless dehydrogenation and hydrogen autotransfer strategy.

Bifunctional Iron Complexes Catalyzed Alkylation of Indoles

Cyclopentadienone iron carbonyl complexes have been applied in alkylation of indoles with various benzylic alcohols, aliphatic alcohols (butanol, ethanol, methanol and 2-methylpentanol) via the hydrogen autotransfer strategy in mild reaction conditions. Experimental works highlight the role of the bifunctional iron complexes and the base. These iron complexes demonstrated a broad applicability in mild conditions and extended the scope of substrates in iron catalyzed C?C bond formation. (Figure presented.).

Tandem organocatalysis and photocatalysis: An anthraquinone-catalyzed indole-c3-alkylation/photooxidation/1,2-shift sequence

Quinones exhibit orthogonal ground- and excited-state reactivities and are therefore highly suitable organocatalysts for the development of sequential catalytic processes. Herein, the discovery of an anthraquinone-catalyzed thermal indole-C3-alkylation with benzylamines is described, which can be combined sequentially with a new visible-light-driven catalytic photooxidation/1,2-shift reaction. The one-flask tandem process converts indoles into 3-benzylindole intermediates, which are further transformed into new fluorescent 2,2-disubstituted indoline-3-one derivatives.

Environmentally friendly and regioselective C3-alkylation of indoles with alcohols through a hydrogen autotransfer strategy

The direct alkylation of indoles using KOH and alcohols, as initial source of the electrophile, under solvent-free conditions is a safe and environmentally benign strategy for selective modification of these structures at the C 3-position, without using hazardous and difficult to handle bromide or iodide derivatives or toxic and expensive transition metal catalysts. The protocol shows a broad scope, including halogenated indoles and secondary alcohols.

Transition-Metal-Catalyzed Regioselective Alkylation of Indoles with Alcohols

The regioselective alkylation of indoles with alcohols as alkylating reagents was developed by using Pd/C or RuCl2(PPh3) 3/DPEphos {DPEphos = bis[(2-diphenylphosphanyl)phenyl] ether}as catalysts. The reaction of indole with benzyl alcohol in the presence of Pd/C and K2CO3 at 80 °C for 24 h without any solvent under in air yielded 90 % of 3-benzylindole. The corresponding 3-benzylindole was obtained in 99 % yield when the reaction was catalyzed by RuCl 2(PPh3)3/DPEphos in the presence of K 3PO4 at 165 °C for 24 h under argon. Several types of alcohols were treated with indoles under these conditions to give the corresponding 3-alkylated indoles in high yields (up to 99 %). This reaction may involve the catalyst-mediated transformation of alcohols to aldehydes, nucleophilic addition of indole to the resulting aldehydes accompanied by dehydration, and then hydrogenation. Copyright

Rapid and general protocol towards catalyst-free friedel-crafts C-alkylation of indoles in water assisted by microwave irradiation

An efficient and simplified protocol for uncatalyzed FriedelCrafts alkylation of indoles using microwave irradiation in water is described. A series of functionalized indole derivatives has been synthesized in very short times with moderate to good yields. The combination of microwave irradiation and superheated water offers significant advantages over conventional methods, such as higher selectivities, simplicity, shorter reaction times, and no need for a catalyst.

[Cp*IrCl2]2-catalyzed indirect functionalization of alcohols: Novel strategies for the synthesis of substituted indoles

We report novel iridium(III)-catalyzed reactions that afford substituted indoles via the indirect functionalization of alcohols via C-3 selective alkylation of indoles with alcohols and a one-pot cascade strategy from amino- or nitro-phenyl ethyl alcohols, which incorporates oxidative cyclization and C-3 alkylation.

Palladium-catalyzed enantioselective C-3 allylation of 3-substituted-1H- indoles using trialkylboranes

We have developed a new enantioselective C-3 allylation of 3-substituted indoles using allyl alcohol and trialkylboranes. Asymmetric syntheses of 3,3-disubstituted indolines and indolenines in enantiomeric excesses up to 90% have been achieved using the bulky borane 9-BBN-C6H13 as the promoter of the reaction. The dependence of the selectivity on the nature of the borane suggests that the boron reagent has a role beyond promoting ionization of the allyl alcohol. A protocol for oxidation of indolenines to oxindoles has also been developed and led to a formal synthesis of (-)-phenserine. Copyright