149065-75-8

Basic information

• Product Name: (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline
• Synonyms: (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline
• CAS NO: 149065-75-8
• Molecular Weight: 243.329
• Mol File: 149065-75-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline(149065-75-8)
• EPA Substance Registry System: (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline(149065-75-8)

Safety Data

• Hazardous Substances Data: 149065-75-8(Hazardous Substances Data)

Usage

Description

(4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline is a chiral chemical compound belonging to the class of oxazolines. It features a molecular structure with a benzene ring connected to a chiral oxazoline ring, which includes a thienyl group. (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline is known for its unique (4S) configuration and is characterized by its non-superimposable mirror image.

Uses

Used in Asymmetric Catalysis:
(4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline is utilized as a versatile ligand in asymmetric catalysis, which is a crucial technique in organic synthesis. Its application in this field is significant for the creation of chiral molecules, which are essential in various chemical and pharmaceutical processes.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline serves as a valuable building block for the synthesis of bioactive compounds. Its unique molecular structure and chiral properties make it a promising candidate for the development of new drugs and therapeutic agents.
Used in Agrochemical Industry:
Similarly, in the agrochemical industry, (4S)-4-benzyl-2-(2-thienyl)-1,3-oxazoline is employed as a key component in the synthesis of bioactive molecules. Its application in this field contributes to the development of novel agrochemicals, such as pesticides and other products that can enhance agricultural productivity and crop protection.

Upstream product

• 1003-31-2 thiophene-2-carbonitrile 
• 3182-95-4 L-Phenylalaninol 
• 527-72-0 2-thiophenylcarboxylic acid 

Relevant articles and documents

Bromotriphenylphosphonium salt promoted tandem one-pot cyclization to optically active 2-Aryl-1,3-oxazolines

Optically active 2-aryl-1,3-oxazolines, such as aromatic carbocycles, heterocycle-binding 4-benzyl (or phenyl)-1,3oxazolines and their 5-benzyl (or phenyl)-l,3-oxazoline isomers were successfully prepared through a bromotriphenylphosphonium salt promoted aziridine ring formation and ring opening sequential process involving tandem one pot cyclization of chiral 2-amino-3-phenylpropanol or 2amino-2-phenylethanol with various aromatic acids in toluene at 90 °C in moderate to excellent yields. The mechanism of this tandem process was also substantiated experimentally.

Preparation of Novel Sulfur and Phosphorus Containing Oxazolines as Ligands for Asymmetric Catalysis

The preparation of enantiomerically pure ligands which contain both an oxazoline group and an additional sulfur or phosphorus donor atom are described.Methylthiomethyl, o-thioanisyl and thienyl oxazolines have been prepared in one step, and o-diphenylphosphinophenyl oxazolines have been prepared in two steps in good yields from commercially available starting materials.

Enantioselective palladium catalysed allylic substitution with thienyl oxazoline ligands

Homochiral thienyl oxazolines have been employed as ligands for enantioselective palladium catalysed allylic substitution. The ligands are straightforward to prepare in one step from commercially available materials and afford good levels of asymmetric induction in the catalytic allylic substitution process of up to 81% ee. The stereochemical outcome is described in terms of steric and electronic factors.