123618-06-4

Basic information

• Product Name: (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine
• Synonyms: (4S,5R)-3,4-Dimethyl-5-phenyl-1,3-oxazolidine; oxazolidine, 3,4-dimethyl-5-phenyl-, (4S,5R)-; Oxazolidine, 3,4-dimethyl-5-phenyl-, (4S-cis)-; Oxazolidine, 3,4-dimethyl-5-phenyl-, cis-
• CAS NO: 123618-06-4
• Molecular Formula: C₁₁H₁₅NO
• Molecular Weight: 177.2429
• Mol File: 123618-06-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 256.9°C at 760 mmHg
• Flash Point: 75.2°C
• Density: 1.012g/cm³
• Vapor Pressure: 0.015mmHg at 25°C
• Refractive Index: 1.516
• CAS DataBase Reference: (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine(123618-06-4)
• EPA Substance Registry System: (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine(123618-06-4)

Safety Data

• Hazardous Substances Data: 123618-06-4(Hazardous Substances Data)

Usage

Description

(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine is a chiral chemical compound belonging to the oxazolidine family. It features a five-membered ring with an oxygen and a nitrogen atom, along with two stereocenters at the 4S and 5R positions. The molecule also has two methyl groups at the 3rd and 4th positions and a phenyl group attached to the 5th position, which imparts aromatic properties to the compound. Oxazolidines, including this specific variant, have garnered significant interest due to their potential applications in various fields such as organic synthesis, catalysis, and pharmaceutical chemistry. The unique stereochemistry and substitution pattern of (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine contribute to its distinct reactivity and biological activity, positioning it as a promising candidate for further research and development.

Uses

Used in Organic Synthesis:
(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine is utilized as a key intermediate in organic synthesis for the preparation of various complex organic molecules. Its unique structure and reactivity make it a valuable building block for the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Catalysis:
In the field of catalysis, (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine serves as a chiral catalyst or ligand, facilitating asymmetric reactions and enhancing the selectivity of chemical transformations. Its stereochemistry plays a crucial role in determining the enantioselectivity and efficiency of catalytic processes.
Used in Pharmaceutical Chemistry:
(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine is employed as a potential pharmaceutical agent or as a precursor for the development of new drugs. Its unique structure and biological activity make it a candidate for the treatment of various diseases, including infectious diseases, neurological disorders, and cancer.
Used in Chiral Pool Synthesis:
(4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine is used as a chiral building block in the synthesis of enantiomerically pure compounds. Its specific stereochemistry allows for the creation of chiral centers in target molecules, which is essential for the development of enantioselective synthetic routes and the production of single-enantiomer pharmaceuticals.
Used in Material Science:
In material science, (4S,5R)-3,4-dimethyl-5-phenyl-1,3-oxazolidine can be used as a component in the design and synthesis of novel materials with specific properties, such as chiral polymers, liquid crystals, or self-assembling systems. Its unique structure and functional groups contribute to the development of materials with tailored properties for various applications, including sensors, catalysts, and drug delivery systems.

Upstream product

• 50-00-0 formaldehyd 
• 90-81-3 ephedrine 
• 90-82-4 rac-pseudoephedrine 
• 1047392-28-8 methyl 2-(N-acetylamino)-5-ethynylbenzoate 
• 299-42-3 ephedrine 
• 74-95-3 1,1-dibromomethane 
• 1806-29-7 2,2'-dihydroxybiphenyl 
• 75-09-2 dichloromethane 

Downstream Products

• 462871-54-1 {[((1S,2R)-2-Chloro-1-methyl-2-phenyl-ethyl)-methyl-amino]-methyl}-phosphonic acid diethyl ester 
• 462871-70-1 ((2R,3S,4S)-1,4-Dimethyl-3-phenyl-azetidin-2-yl)-phosphonic acid diethyl ester 
• 462871-39-2 {[((1S,2R)-2-Hydroxy-1-methyl-2-phenyl-ethyl)-methyl-amino]-methyl}-phosphonic acid diethyl ester 
• 552-79-4 (-)-N-methylephedrine 
• 50-47-5 desipramine 
• 76503-86-1 (2R, 3S)-3,4,6-Trimethyl-7-morpholino-2-phenylhexahydro-1,4-oxazepin 
• 76503-94-1 (2R, 4S, 5R)-2-Isopropenyl-3,4-dimethyl-5-phenyl-1,3-oxazolidin 
• 76503-95-2 (2S, 4S, 5R)-2-Isopropenyl-3,4-dimethyl-5-phenyl-1,3-oxazolidin 
• 76503-87-2 (2R, 3S)-c-7-Dimethylamino-3,4,r-6-trimethyl-2-phenylhexahydro-1,4-oxazepin 
• 15451-14-6 3-dimethylamino-2,2-dimethylpropanal 
• 76503-82-7 3,4,6,6-Tetramethyl-7-dimethylamino-2-phenylhexahydro-1,4-oxazepin 
• 23588-51-4 2,2-dimethyl-3-(N-morpholino)propanal 
• 76503-78-1 3,4,6,6-Tetramethyl-7-morpholino-2-phenylhexahydro-1,4-oxazepin 
• 123387-83-7 (1R,2S)-2-[Methyl-(5-methyl-furan-2-ylmethyl)-amino]-1-phenyl-propan-1-ol 

Relevant articles and documents

Condensation of chiral 1,3-oxazolidines with cathecol and 4,4'- dibromobiphenol: New enantiopure polydentate ligands with C2-symmetry

The new enantiopure polydentate ligands 3a,c and 4a-c have been synthesized via Mannich condensation of 1,3-oxazolidines 1a-c with 5,5'- dibromobiphenol and cathecol. The products are enantiopure C2 chiral ligands of potential use in asymmetric synthesis as well as bioactive compounds.

Study of alkaloids of the Siberian and Altai flora 14. Synthesis of alkaloid-based tertiary N-(3-arylprop-2-ynyl)amines

3-Arylprop-2-ynylamines containing the key fragment of known alkaloids of the Altai flora were synthesized by the Sonogashira and Mannich reactions.

Reaction of 3-methylamino-1,2-diols with dihalomethanes. Synthesis of chiral 4-substituted 3-methyltetrahydro-1,3-oxazin-5-ols

Enantiomerically pure 4,5-disubstituted 3-methyltetrahydro-1,3-oxazines have been obtained by reaction of 3-methylamino-1,2-diols with dichloromethane by regioselective differentiation of hydroxyl groups. (C) 2000 Published by Elsevier Science Ltd.