1016275-45-8

Basic information

• Product Name: (S)-2-(4’-methylphenyl)-1,2,3,4-tetrahydroquinoline
• Synonyms: (S)-2-(4’-methylphenyl)-1,2,3,4-tetrahydroquinoline
• CAS NO: 1016275-45-8
• Molecular Weight: 223.318
• Mol File: 1016275-45-8.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: (S)-2-(4’-methylphenyl)-1,2,3,4-tetrahydroquinoline(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-(4’-methylphenyl)-1,2,3,4-tetrahydroquinoline(1016275-45-8)
• EPA Substance Registry System: (S)-2-(4’-methylphenyl)-1,2,3,4-tetrahydroquinoline(1016275-45-8)

Safety Data

• Hazardous Substances Data: 1016275-45-8(Hazardous Substances Data)

Upstream product

• 1198359-64-6 2-(4-methylphenyl)quinoline hydrobromide 
• 24667-94-5 2-(4-methylphenyl)quinoline 
• 122-00-9 para-methylacetophenone 
• 552-89-6 2-nitro-benzaldehyde 
• 958261-72-8 C₁₆H₁₅NO 
• 612-62-4 2-Chloroquinoline 
• 5720-05-8 4-methylphenylboronic acid 
• 123612-59-9 1,2,3,4-tetrahydro-2-(4-methylphenyl)quinoline 
• 1159987-18-4 2-(3-p-tolylprop-2-ynyl)aniline 

Relevant articles and documents

Catalytically Asymmetric Pd/Norbornene Catalysis: Enantioselective Synthesis of (+)-Rhazinal, (+)-Rhazinilam, and (+)-Kopsiyunnanine C1-3

A catalytically asymmetric palladium/norbornene-catalyzed reaction is reported, where α-aryl tetrahydroquinoline derived phosphoramidite L15 is found to be the optimum ligand. Taking advantage of this transformation, the concise and unified enantioselective syntheses of (+)-rhazinal, (+)-rhazinilam, and (+)-kopsiyunnanine C1, C2, and C3 are realized.

Exploration of chiral diastereomeric spiroketal (SPIROL)-based phosphinite ligands in asymmetric hydrogenation of heterocycles

New and readily available chiral SPIROL-based diphosphinite ligands (SPIRAPO) have been prepared and employed for iridium-catalyzed asymmetric hydrogenations of quinolines, quinoxalines and 2H-1,4-bezoxazin-2-ones. While the structurally similar (R,R,R)-SPIRAPO and (R)-SPINOL-based phosphinites were not the best ligands for these transformations, the (S,R,R)-diastereomer of SPIRAPO was found to be highly effective ligand for the reduction of 20 different heterocyclic systems with loadings as low as S/C = 10?000. This dearomatizative hydrogenation provided direct access to optically active tetrahydroquinolines in high enantioselectivities (up to 94percent ee) and excellent yields (up to 99percent), and was used to generate 1.75 g of natural alkaloid (-)-(R)-angustureine. This protocol was subsequently extended to achieve asymmetric hydrogenation of quinoxalines and 2H-1,4-benzoxazin-2-ones in good to excellent enantioselectivities.

Enantioselective Synthesis of Tetrahydroquinolines from 2-Aminochalcones via a Consecutive One-Pot Reaction Catalyzed by Chiral Phosphoric Acid

A new asymmetric protocol for the synthesis of chiral tetrahydroquinolines from 2-aminochalcones via a two-step one-pot consecutive process (cyclization/asymmetric reduction) has been developed using chiral phosphoric acid as the sole catalyst. 2-Aminochalcones were converted into the corresponding quinolines through chiral phosphoric acid-catalyzed dehydrative cyclization, and the resultant quinolines were subsequently reduced to the chiral tetrahydroquinolines via chiral phosphoric acid-catalyzed asymmetric reduction with Hantzsch ester. Various 2-aminochalcones could be applicable to this protocol, and the desired tetrahydroquinolines were obtained in excellent yields and with excellent enantioselectivities. Furthermore, the utility of this protocol has been successfully demonstrated in the highly efficient synthesis of estrogen receptor modulator.