917377-78-7

Basic information

• Product Name: (2S)-2,3-DIHYDRO-2-PHENYL-1H-INDOLE
• Synonyms: (2S)-2,3-DIHYDRO-2-PHENYL-1H-INDOLE
• CAS NO: 917377-78-7
• Molecular Formula: C14H13N
• Molecular Weight: 195.26
• Mol File: 917377-78-7.mol
• Article Data: 32

Chemical Properties

• Boiling Point: 330°C at 760 mmHg
• Flash Point: 163.1°C
• Appearance: /
• Density: 1.092g/cm³
• Vapor Pressure: 0.000171mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: (2S)-2,3-DIHYDRO-2-PHENYL-1H-INDOLE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2,3-DIHYDRO-2-PHENYL-1H-INDOLE(917377-78-7)
• EPA Substance Registry System: (2S)-2,3-DIHYDRO-2-PHENYL-1H-INDOLE(917377-78-7)

Safety Data

• Hazardous Substances Data: 917377-78-7(Hazardous Substances Data)

Usage

Description

(2S)-2,3-Dihydro-2-phenyl-1H-indole is a chiral indole derivative characterized by its (2S) configuration, where the 2nd carbon atom has a left-handed orientation. (2S)-2,3-DIHYDRO-2-PHENYL-1H-INDOLE features a phenyl group attached to the 3rd carbon of the indole ring, which imparts unique chemical and pharmacological properties. Indole derivatives are recognized for their wide range of biological activities, such as antimicrobial, anticancer, and neurological effects. Further research is required to explore the full potential and applications of (2S)-2,3-dihydro-2-phenyl-1H-indole.

Uses

Used in Pharmaceutical Industry:
(2S)-2,3-Dihydro-2-phenyl-1H-indole is used as a pharmaceutical compound for its potential antimicrobial, anticancer, and neurological effects. The specific chemical properties due to the phenyl group attachment may contribute to its therapeutic applications, although more research is needed to confirm its efficacy and safety.
Used in Chemical Research:
In the field of chemical research, (2S)-2,3-dihydro-2-phenyl-1H-indole serves as a subject for studying the effects of chirality and structural variations on the biological activity of indole derivatives. This can lead to the development of new drugs and therapies based on a better understanding of the compound's properties and interactions.

InChI:InChI=1/C14H13N/c1-2-6-11(7-3-1)14-10-12-8-4-5-9-13(12)15-14/h1-9,14-15H,10H2/t14-/m0/s1

Upstream product

• 948-65-2 2-phenyl-indole 
• 67-56-1 methanol 
• 164398-51-0 2-(2-Phenylethyl)phenyl azide 
• 64-17-5 ethanol 
• 123-91-1 1,4-dioxane 
• 71-48-7 cobalt(II) acetate 
• 71-43-2 benzene 
• 7647-01-0 hydrogenchloride 
• 7732-18-5 water 
• 5697-85-8 2-(2-phenylethyl)aniline 
• 451-40-1 phenyl benzyl ketone 
• 4212-33-3 2-(2-nitrophenyl)-1-phenylethanone 
• 5877-55-4 N-benzylidene-2-methylaniline 
• 103-80-0 phenylacetyl chloride 

Downstream Products

• 101782-76-7 1-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-phenyl-2,3-dihydro-indole 
• 3780-04-9 2-phenyl-indole-4,5-dione 

Relevant articles and documents

Asymmetric Synthesis of 2-Arylindolines and 2,2-Disubstituted Indolines by Kinetic Resolution

Kinetic resolution of 2-arylindolines (2,3-dihydroindoles) was achieved by treatment of their N-tert-butoxycarbonyl (Boc) derivatives with n-butyllithium and sparteine in toluene at ?78 °C followed by electrophilic quench. The unreacted starting materials together with the 2,2-disubstituted products could be isolated with high enantiomer ratios. Variable temperature NMR spectroscopy showed that the rate of Boc rotation was fast (ΔG≠≈57 kJ/mol at 195 K). This was corroborated by DFT studies and by in situ ReactIR spectroscopy. The enantioenriched N-Boc-2-arylindolines were converted to 2,2-disubstituted products without significant loss in enantiopurity. Hence, either enantiomer of the 2,2-disubstituted products could be obtained with high selectivity from the same enantiomer of the chiral ligand sparteine (one from the kinetic resolution and the other from subsequent lithiation-trapping of the recovered starting material). Secondary amine products were prepared by removing the Boc group with acid to provide a way to access highly enantioenriched 2-aryl and 2,2-disubstituted indolines.

Covalent Organic Frameworks toward Diverse Photocatalytic Aerobic Oxidations

Photoactive two-dimensional covalent organic frameworks (2D-COFs) have become promising heterogenous photocatalysts in visible-light-driven organic transformations. Herein, a visible-light-driven selective aerobic oxidation of various small organic molecules by using 2D-COFs as the photocatalyst was developed. In this protocol, due to the remarkable photocatalytic capability of hydrazone-based 2D-COF-1 on molecular oxygen activation, a wide range of amides, quinolones, heterocyclic compounds, and sulfoxides were obtained with high efficiency and excellent functional group tolerance under very mild reaction conditions. Furthermore, benefiting from the inherent advantage of heterogenous photocatalysis, prominent sustainability and easy photocatalyst recyclability, a drug molecule (modafinil) and an oxidized mustard gas simulant (2-chloroethyl ethyl sulfoxide) were selectively and easily obtained in scale-up reactions. Mechanistic investigations were conducted using radical quenching experiments and in situ ESR spectroscopy, all corroborating the proposed role of 2D-COF-1 in photocatalytic cycle.

Asymmetric Transfer Hydrogenation of N-Unprotected Indoles with Ammonia Borane

A metal-free asymmetric transfer hydrogenation of unprotected indoles was successfully realized using a catalyst derived from HB(C6F5)2 and (S)-tert-butylsulfinamide with ammonia borane as a hydrogen source. A variety of indolines were achieved in 40-78percent yields with up to 90percent ee.