1228543-12-1

Basic information

• Product Name: (S)-2-P-TOLYLPIPERIDINE
• Synonyms: (S)-2-P-TOLYLPIPERIDINE
• CAS NO: 1228543-12-1
• Molecular Formula: C₁₂H₁₇N
• Molecular Weight: 175.27
• Mol File: 1228543-12-1.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-2-P-TOLYLPIPERIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-P-TOLYLPIPERIDINE(1228543-12-1)
• EPA Substance Registry System: (S)-2-P-TOLYLPIPERIDINE(1228543-12-1)

Safety Data

• Hazardous Substances Data: 1228543-12-1(Hazardous Substances Data)

Usage

Description

(S)-2-P-TOLYLPIPERIDINE, with the molecular formula C14H19N, is a piperidine derivative featuring a tolyl (methylphenyl) group attached to the piperidine ring. As a chiral molecule, it possesses specific stereochemistry, making it a crucial component in the synthesis of pharmaceuticals and other organic compounds. Its unique structure and properties render it valuable in various applications across the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Synthesis:
(S)-2-P-TOLYLPIPERIDINE is used as a key intermediate in the pharmaceutical industry for the production of various drugs and fine chemicals. Its unique structure allows for the creation of new compounds with potential therapeutic applications.
Used in Chemical Industry:
In the chemical industry, (S)-2-P-TOLYLPIPERIDINE serves as a versatile building block for the synthesis of a wide range of organic compounds. Its specific stereochemistry makes it an essential component in the development of novel materials and chemical products.
Used in Drug Development:
(S)-2-P-TOLYLPIPERIDINE is utilized as a starting material in drug development, where its chiral nature can be exploited to create enantiomerically pure compounds with improved pharmacological properties and reduced side effects.
Used in Chiral Catalysts:
Due to its chiral properties, (S)-2-P-TOLYLPIPERIDINE can be employed as a chiral catalyst in asymmetric synthesis, enabling the production of enantiomerically enriched compounds with high selectivity and efficiency.
Used in Research and Development:
(S)-2-P-TOLYLPIPERIDINE is also used in research and development settings to study the effects of stereochemistry on the biological activity of compounds, as well as to develop new methods for the synthesis of chiral molecules.

Upstream product

• 105902-02-1 6-p-tolyl-2,3,4,5-tetrahydro-pyridine 
• 833-85-2 5-(4-methylphenyl)-5-oxopentanoic acid 

Relevant articles and documents

Enzyme Cascades in Whole Cells for the Synthesis of Chiral Cyclic Amines

The increasing diversity of reactions mediated by biocatalysts has led to development of multistep in vitro enzyme cascades, taking advantage of generally compatible reaction conditions. The construction of pathways within single whole cell systems is much less explored, yet has many advantages. Herein we report the generation of a successful whole cell de novo enzyme cascade for the diastereoselective and/or enantioselective conversion of simple, linear keto acids into valuable cyclic amine products. The pathway starts with carboxylic acid reduction that triggers a transamination, imine formation, and subsequent imine reduction. Construction and optimization of the system was achieved by standard genetic manipulation and the cascade required only starting material, amine donor, and whole cell catalyst with cofactors provided internally by glucose metabolism. A panel of synthetic keto acids provided access to piperidines in high conversions (up to 93%) and enantiomeric excess (up to 93%).

An (R)-imine reductase biocatalyst for the asymmetric reduction of cyclic imines

Although the range of biocatalysts available for the synthesis of enantiomerically pure chiral amines continues to expand, few existing methods provide access to secondary amines. To address this shortcoming, we have over-expressed the gene for an (R)-imine reductase [(R)-IRED] from Streptomyces sp. GF3587 in Escherichia coli to create a recombinant whole-cell biocatalyst for the asymmetric reduction of prochiral imines. The (R)-IRED was screened against a panel of cyclic imines and two iminium ions and was shown to possess high catalytic activity and enantioselectivity. Preparative-scale synthesis of the alkaloid (R)-coniine (90 % yield; 99 % ee) from the imine precursor was performed on a gram-scale. A homology model of the enzyme active site, based on the structure of a closely related (R)-IRED from Streptomyces kanamyceticus, was constructed and used to identify potential amino acids as targets for