22160-13-0

Basic information

• Product Name: (2R)-2α-Methylindoline
• Synonyms: (2R)-2,3-Dihydro-2-methyl-1H-indole;(2R)-2α-Methylindoline;(R)-2,3-Dihydro-2-methyl-1H-indole;(2R)-2-methyl-2,3-dihydro-1H-indole;1H-Indole, 2,3-dihydro-2-methyl-, (2R)-
• CAS NO: 22160-13-0
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• Mol File: 22160-13-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (2R)-2α-Methylindoline(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2α-Methylindoline(22160-13-0)
• EPA Substance Registry System: (2R)-2α-Methylindoline(22160-13-0)

Safety Data

• Hazardous Substances Data: 22160-13-0(Hazardous Substances Data)

Usage

Uses

Used in Biochemistry:
(2R)-2α-Methylindoline is used as a stereoselective catalyst for its ability to affect physiological functions in organisms, which is crucial in the field of biochemistry.
Used in Medicine:
(2R)-2α-Methylindoline is used as an interacting agent for its capacity to interact with enzymes and proteins, which is essential in the development of pharmaceuticals and therapeutic applications.
Used in Biotechnology:
(2R)-2α-Methylindoline is used as a catalyst in biotechnological processes, leveraging its stereoselective properties to enhance the efficiency and specificity of biochemical reactions in biotechnological applications.

Upstream product

• 54731-09-8 N-tosyl-L-prolyl chloride 
• 6872-06-6 2-methyl indoline 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 147851-69-2 (R)-2-phenoxypropionyl chloride 
• 95-20-5 2-methyl-1H-indole 

Downstream Products

• 1448544-28-2 C₁₆H₁₄BrNO 
• 517866-45-4 1-(chloroacetyl)-2-methylindoline 

Relevant articles and documents

Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst

The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.

Acylative kinetic resolution of racemic heterocyclic amines with (R)-2-phenoxypropionyl chloride

The acylative kinetic resolution of racemic heterocyclic amines such as 3,4-dihydro-3-methyl-2H-[1,4]benzoxazines, 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine, 2-methyl-1,2,3,4-tetrahydro-quinolines and 2-methylindoline with enantiopure (R)-2-phenoxypropionyl chloride has been studied. It has been found that acylation of 3,4-dihydro-3-methyl-2H-[1,4]benzothiazine proceeds with the best stereoselectively when compared with other racemic amines. An efficient method for the preparation of (S)-3,4-dihydro-3-methyl-2H-[1,4]benzothiazine (99.4% ee) via a kinetic resolution protocol was developed. The possibility of recycling (R)-2-phenoxypropionic acid has been demonstrated.

Iridium-catalyzed asymmetric hydrogenation of N-protected indoles

Chiral indolines substituted at C-2 or C-3 can be prepared in high yield and excellent enantioselectivity by asymmetric hydrogenation of N-protected indoles by using Ir catalysts with chiral N,P ligands. With less reactive substrates, the reaction had to

Kinetic resolution of (±)-2,3-dihydro-3-methyl-4H-1,4-benzoxazine, (±)-2-methyl-1,2,3,4-tetrahydroquinoline and (±)-2-methylindoline using N-tosyl-(S)-prolyl chloride

Acylation of racemic 2,3-dihydro-3-methyl-4H-1,4-benzoxazine, 2-methyl-1,2,3,4-tetrahydroquinoline and 2-methylindoline with N-tosyl-(S)-prolyl chloride resulted in their kinetic resolution with the predominant formation of (R,S)-diastereoisomeric amides,