64625-19-0

Usage

Uses

Used in Agricultural Industry:
(S)-Homopipecolic acid is used as a signaling molecule for enhancing plant defense mechanisms against environmental stress. Its role in the synthesis of jasmonic acid helps regulate the balance of growth and defense in plants, making it a valuable tool for improving crop resilience and productivity.
Used in Antimicrobial Applications:
(S)-Homopipecolic acid is used as an antimicrobial agent for its potential activity against phytopathogenic bacteria and fungi. This property can be harnessed to develop new strategies for controlling plant diseases and reducing the reliance on chemical pesticides.
Used in Anti-Inflammatory Applications:
(S)-Homopipecolic acid is used as an anti-inflammatory agent due to its demonstrated properties. While primarily studied in the context of plant biology, its anti-inflammatory effects could potentially be explored for applications in other areas, such as medicine or veterinary science, where controlling inflammation is beneficial.
Used in Plant Biology Research:
(S)-Homopipecolic acid is used as a research tool to study the complex mechanisms of plant stress responses and defense systems. Understanding its role in these processes can contribute to the development of more robust and adaptable plant varieties, as well as inform strategies for managing plant health in the face of environmental challenges.

Upstream product

• 103639-57-2 (2S)-2-(2-methoxyethyl)piperidine 
• 290835-82-4 tert-butyl (S)-piperidine-2-acetate 
• 171866-64-1 (2S)-methoxycarbonylmethylpiperidin 
• 18261-30-8 (E,E)-methyl heptan-2,5-dieneoate 
• 68419-38-5 (2R)-2-(2-methoxyethyl)piperidine 
• 761457-26-5 (2R)-1-methoxycarbonyl-2-carbethoxymethyIpiperidine 
• 542-05-2 acetonedicarboxylic acid 
• 1369774-33-3 (1R,5R)-9-benzyloxycarbonylamino-2-oxo-1-oxabicyclo[3.3.1]nonane 
• 1369774-32-2 7-benzyloxycarbonylazabicyclo-[3.2.1]octan-6-one 
• 1369774-31-1 (1R,5S,6S)-N-benzyloxycarbonyl-6-tropanol 
• 1369774-30-0 (1R,5S,6R)-6-tropanol 
• 1369774-34-4 (1R,5S,6R)-6-tropanol (R,R)-tartrate 
• 1369774-29-7 6-tropanol 
• 1202040-37-6 tert-butyl (R)-2-(piperidin-2'-yl)ethanoate 

Downstream Products

• 131134-77-5 (S)-2-(methoxycarbonylmethyl)piperidine-1-carboxylic acid tert-butyl ester 
• 159898-10-9 (S)-2-{1-[(tert-butoxy)carbonyl]piperidin-2-yl}acetic acid 
• 1036403-99-2 (R)-2-[(N-benzyloxycarbonyl)piperidin-2-yl]ethanoic acid 
• 351410-32-7 (R)-2-(1-(tert-butoxycarbonyl)piperidin-2-yl) acetic acid 

Relevant academic research and scientific papers

Syntheses of (-)-pelletierine and (-)-homopipecolic acid

Enantiomeric syntheses of (-)-homopipecolic acid and (-)-pelletierine have been achieved by chiral resolution of tropanol followed by Baeyer-Villiger oxidation. The methodology provides a practical route for the synthesis of optically pure piperidines. The Royal Society of Chemistry 2012.

Hydroformylation of alkenylamines. Concise approaches toward piperidines, quinolizidines, and related alkaloids

Linear hydroformylation of N-protected allyl- or homoallylamines (cyclohydrocarbonylation: CHC), followed by a reductive amination constitute the two key steps toward convenient routes to aza-heterocycles.

Asymmetric synthesis of Sedum alkaloids via lithium amide conjugate addition

Conjugate addition of lithium (R)-N-allyl-N-(α-methylbenzyl)amide or lithium (R)-N-but-3-enyl-N-(α-methylbenzyl)amide to an alkyl hexa-2,4-dienoate or alkyl hepta-2,6-dienoate, followed by ring-closing metathesis of the olefin functionalities within the resultant β-amino ester, generates a range of diastereoisomerically pure azacycles in good yield. These homochiral templates are readily transformed to a range of piperidine alkaloids of the Sedum family, and the corresponding five-, seven- and eight-membered ring homologues.

Improved protocol for asymmetric, intramolecular heteroatom Michael addition using organocatalysis: Enantioselective syntheses of homoproline, pelletierine, and homopipecolic acid

(Chemical Equation Presented) An improved protocol for the construction of enantioenriched pyrrolidine, indoline, and piperidine rings using an organocatalyzed, intramolecular heteroatom Michael addition is described. Application to the enantioselective synthesis of homoproline, homopipecolic acid, and pelletierine has been accomplished.

PROCESS FOR THE ENANTIOSELECTIVE PRODUCTION OF AN AMINO ACID DERIVATIVE COMPRISING AT LEAST ONE NITROGENOUS HETEROCYCLE

Process for the enantioselective production of an amino acid derivative comprising at least one nitrogenous heterocycle, said heterocycle being substituted with at least one side chain comprising a functional group of carboxyl type, such as a carboxyl group, an ester group or an amide group, which process comprises at least one step in which a prochiral unsaturated amino acid derivative of formula (I) is subjected to hydrogenation in the presence of an enantiopure hydrogenation catalyst.

An efficient synthesis of chiral cyclic β-amino acids via asymmetric hydrogenation

Cyclic β-amino acids, homoproline, homopipecolic acid and 3-carboxy-methylmorpholine were obtained in high enantiomeric excesses by transition metal-catalyzed asymmetric hydrogenation of cyclic β-acylamino-alkenoates. These compounds were synthesized by a

PROCESS FOR PREPARATION OF PIPERIDIN-2-YLACETIC ACID

Piperidin-2-ylacetic acid (II) is efficiently and safely produced in industrial scale by treating piperidin-2-ylethanol (I) with 2,2,6,6-tetramethylpiperidin-1-oxyl, sodium hypochlorite and sodium chlorite in a two phase solvent comprising an organic solvent and water without using strongly toxic chromium trioxide.

Asymmetric synthesis of cyclic β-amino acids and cyclic amines via sequential diastereoselective conjugate addition and ring closing metathesis

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to a range of α,β-unsaturated esters followed by ring closing metathesis is used to afford efficiently a range of substituted cyclic β-amino esters in high d.e. Alternatively, conjugate addition to α,β-unsaturated Weinreb amides, functional group conversion and ring closing metathesis affords cyclic amines in high d.e. The further application of this methodology to the synthesis of a range of carbocyclic β-amino esters via conjugate addition, enolate alkylation and ring closing metathesis is also described. Application of this methodology affords, after deprotection, (S)-homoproline, (S)-homopipecolic acid, (S)-coniine and (1S,2S)-trans-pentacin.

Ring closing metathesis for the asymmetric synthesis of (S)-homopipecolic acid, (S)-homoproline and (S)-coniine

Diastereoselective conjugate addition of lithium (S)-N-allyl-N-α-methylbenzylamide to α,β-unsaturated esters or Weinreb amides, followed by ring closing metathesis is used to afford the cyclic β-amino acids (S)-homopipecolic acid and (S)-homoproline and the amine (S)-coniine in high ee.

A practical synthesis of protected β-homolysine

Protected β-homolysine of high enantiomeric purity (ee>99.5%) is prepared utilizing the stereoselective conjugate addition of lithiated (S)-(α-methylbenzyl)benzylamide to (E)-7-(tosyloxy)hept-2-enoic acid tert-butyl ester, followed by subsequent ammonia s