175478-20-3

Basic information

• Product Name: (2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE
• Synonyms: (2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE;(2R,6S)-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine(SALTDATA: FREE);(2R,6S)-6-phenyl-2-prop-2-enyl-1,2,3,6-tetrahydropyridine
• CAS NO: 175478-20-3
• Molecular Formula: C14H17N
• Molecular Weight: 0
• Mol File: 175478-20-3.mol

Chemical Properties

• Boiling Point: 298.3°C at 760 mmHg
• Flash Point: 136.2°C
• Appearance: /
• Density: 0.952g/cm³
• Vapor Pressure: 0.00128mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: (2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE(175478-20-3)
• EPA Substance Registry System: (2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE(175478-20-3)

Safety Data

• Hazardous Substances Data: 175478-20-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry:
(2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE is used as a building block for the synthesis of various pharmaceutical compounds. Its structural features make it a valuable component in the creation of new molecules with potential applications in medicine.
Used in Pharmaceutical Research and Drug Development:
In the pharmaceutical industry, (2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE is utilized for its potential role in the development of new drugs. Its unique structure allows researchers to explore its properties and interactions with biological targets, which can lead to the discovery of novel therapeutic agents.
Used in Medicinal Chemistry and Toxicology:
(2R,6S)-2-ALLYL-6-PHENYL-1,2,3,6-TETRAHYDROPYRIDINE is also a valuable target for study in medicinal chemistry and toxicology. Understanding its interactions with biological systems and potential side effects can provide insights into its safety and efficacy as a component of pharmaceutical compounds.

InChI:InChI=1/C14H17N/c1-2-7-13-10-6-11-14(15-13)12-8-4-3-5-9-12/h2-6,8-9,11,13-15H,1,7,10H2/t13-,14+/m1/s1

Upstream product

• 110-86-1 pyridine 
• 688-61-9 Triallylborane 
• 591-51-5 phenyllithium 

Relevant articles and documents

Preparation of trans- and cis-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines based on the reductive trans-2,6-dialkylation of pyridine. Synthesis of (+/-)-epidihydropinidine and (+/-)-dihydropinidine

A general method for the preparation of unsymmetrical trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridine 6 based on a combination of 1,2-addition of RLi to pyridine and trans-6-allylation with triallylborane in the presence of methanol was elaborated.It was shown that trans-piperidines 6 (R = Alk, Ph) isomerize into the corresponding cis-2-allyl-6-alkyl(phenyl)-3-piperidines 14 on heating with triallylborane followed by deboronation of aminoborane (16) with methanol and an alkali.The stereochemistry of compounds 6 and 14 was determined by two-dimensional NOE spectroscopy.A possible mechanism of the formation of trans-amines 6 and their transformation into cis-isomers discussed.Alkaloids (+/-)-epidihydropinidine (trans-2-methyl-6-propylpiperidine 2a, 70percent) and (+/-)-dihydropinidine (cis-2-methyl-6-propylpiperidine 1d, 71percent) were synthesized by hydrogenation of compound 6a (R = Me) and 14a (R = Me), respectively, over Raney nickel. - Keywords: allylboration; pyridine, 1,2-addition, alkyl(aryl)lithium, triallylborane; trans- and cis-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines; trans-cis-isomerization; stereochemistry; piperidine alkaloids; (+/-)-epidihydropinidine; (+/-)-dihydropinidine.

Synthesis and molecular structure of trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine hydrochloride

When treated with triallylborane and MeOH, the product of the 1,2-addition of PhLi to pyridine transforms to trans-2-allyl-6-phenyl-1,2,3,6-tetrahydropyridine. The structure of its hydrochloride was established by X-ray structural analysis.

Preparation of trans-2-allyl-6-alkyl(aryl)-1,2,3,6-tetrahydropyridines by reductive trans-2,6-dialkylation of pyridine. Synthesis of (±)-epidihydropinidine

A convenient method for the preparation of the title compounds involving the sequential treatment of pyridine with RLi (R = Alk, Ar), triallylborane and methanol is developed.