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16078-30-1

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16078-30-1 Usage

Description

1-Acetylindoline, also known as 1-(2,3-dihydroindol-1-yl)ethanone, is a substituted indole that serves as a key intermediate in the synthesis of various chemical compounds. It is a tertiary amide with bulky N-groups, which can be reduced to the corresponding amine using silane in the presence of a catalyst, such as MoO2Cl2.

Uses

1. Used in Pharmaceutical Industry:
1-Acetylindoline is used as a reactant for the preparation of triazolothiadiazepine dioxide derivatives, which are potentially valuable in the development of new pharmaceutical compounds.
2. Used in Chemical Synthesis:
1-Acetylindoline is used as a reactant for the preparation of halo-substituted aromatic amides, which are important building blocks in the synthesis of various organic compounds.
3. Used in Medicinal Chemistry:
1-Acetylindoline is used as a reactant for the preparation of [[(phenyl)piperazinyl]alkyl]indolyl]ethanone and [[[(phenoxyethyl)piperazinyl]alkyl]indolyl]ethanone derivatives, which are known as α1-adrenoreceptor antagonists. These compounds have potential applications in the treatment of various medical conditions, such as hypertension and benign prostatic hyperplasia.
4. Used in Antimicrobial Agents:
1-Acetylindoline is used as a reactant for the synthesis of naphthalenedione derivatives, which exhibit antimycobacterial activity. These compounds can be used in the development of new drugs to combat tuberculosis and other mycobacterial infections.
5. Used in Organic Chemistry:
1-Acetylindoline is used as a reactant for regioselective ortho Suzuki-Miyaura coupling reactions, which are important for the formation of carbon-carbon bonds in the synthesis of complex organic molecules. This application is relevant in various fields, including pharmaceuticals, materials science, and agrochemicals.

Synthesis Reference(s)

Tetrahedron, 52, p. 7525, 1996 DOI: 10.1016/0040-4020(96)00266-9Tetrahedron Letters, 24, p. 561, 1983 DOI: 10.1016/S0040-4039(00)81464-1

Check Digit Verification of cas no

The CAS Registry Mumber 16078-30-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,6,0,7 and 8 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 16078-30:
(7*1)+(6*6)+(5*0)+(4*7)+(3*8)+(2*3)+(1*0)=101
101 % 10 = 1
So 16078-30-1 is a valid CAS Registry Number.
InChI:InChI=1/C10H11NO/c1-8(12)11-7-6-9-4-2-3-5-10(9)11/h2-5H,6-7H2,1H3

16078-30-1 Well-known Company Product Price

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  • Aldrich

  • (379492)  1-Acetylindoline  98%

  • 16078-30-1

  • 379492-5G

  • 391.95CNY

  • Detail

16078-30-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 1-Acetylindoline

1.2 Other means of identification

Product number -
Other names 1-(2,3-dihydroindol-1-yl)ethanone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:16078-30-1 SDS

16078-30-1Relevant articles and documents

Mild Rh(III)-catalyzed C7-allylation of indolines with allylic carbonates

Park, Jihye,Mishra, Neeraj Kumar,Sharma, Satyasheel,Han, Sangil,Shin, Youngmi,Jeong, Taejoo,Oh, Joa Sub,Kwak, Jong Hwan,Jung, Young Hoon,Kim, In Su

, p. 1818 - 1827 (2015)

The rhodium(III)-catalyzed direct allylation of indolines with allylic carbonates at room temperature is described. These transformations provide the facile and efficient construction of C7-allylated indolic scaffold.

A rapid and clean synthetic approach to cyclic peptides: Via micro-flow peptide chain elongation and photochemical cyclization: Synthesis of a cyclic RGD peptide

Mifune, Yuto,Nakamura, Hiroyuki,Fuse, Shinichiro

, p. 11244 - 11249 (2016)

A cyclic RGD peptide was efficiently synthesized based on micro-flow, triphosgene-mediated peptide chain elongation and micro-flow photochemical macrolactamization. Our approach enabled a rapid (amidation for peptide chain elongation 5 s, macrolactamization 5 min) and clean (only one column chromatographic separation) synthesis of a cyclic peptide.

Cobalt Catalyzed Hydroarylation of Michael Acceptors with Indolines Directed by a Weakly Coordinating Functional Group

Banjare, Shyam Kumar,Chebolu, Rajesh,Ravikumar

, p. 4049 - 4053 (2019)

A cobalt(III) catalyzed hydroarylation of Michael acceptors using indolines, selectively at the C-7 position, has been reported. For the selective C-7 functionalization of indoline, we have used a weakly coordinating amide carbonyl group. During the process of optimization, we have also discovered the unusual cocatalytic activity of zinc triflate in the C-H functionalization reaction. Hydroarylation of unprotected maleimide using indolines was a challenging substrate and never accomplished before, we were able to achieve this with our methodology in good yields.

A New Method for Preparation of 2-Aminopyridine:Borane and its Analogues

Okamoto, Yoshihisa,Osawa, Toshimitsu,Kinoshita, Toshio

, p. 462 - 464 (1982)

-

Method for promoting acylation of amine or alcohol by carbon dioxide

-

Paragraph 0033-0034, (2021/05/29)

The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.

The Relation Between Position and Chemical Composition of Bis-Indole Substituents Determines Their Interactions with G-Quadruplex DNA

Prasad, Bagineni,Das, Rabindra Nath,Jamroskovic, Jan,Kumar, Rajendra,Hedenstr?m, Mattias,Sabouri, Nasim,Chorell, Erik

supporting information, p. 9561 - 9572 (2020/07/09)

G-quadruplex (G4) DNA structures are linked to fundamental biological processes and human diseases, which has triggered the development of compounds that affect these DNA structures. However, more knowledge is needed about how small molecules interact with G4 DNA structures. This study describes the development of a new class of bis-indoles (3,3-diindolyl-methyl derivatives) and detailed studies of how they interact with G4 DNA using orthogonal assays, biophysical techniques, and computational studies. This revealed compounds that strongly bind and stabilize G4 DNA structures, and detailed binding interactions which for example, show that charge variance can play a key role in G4 DNA binding. Furthermore, the structure–activity relationships generated opened the possibilities to replace or introduce new substituents on the core structure, which is of key importance to optimize compound properties or introduce probes to further expand the possibilities of these compounds as tailored research tools to study G4 biology.

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