669015-08-1

Basic information

• Product Name: 1-Boc-4-phenylethynyl-piperidine
• Synonyms: 1-Boc-4-phenylethynyl-piperidine
• CAS NO: 669015-08-1
• Molecular Formula: C₁₈H₂₃NO₂
• Molecular Weight: 285.38072
• Mol File: 669015-08-1.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 400.5°C at 760 mmHg
• Flash Point: 196°C
• Appearance: /
• Density: 1.08g/cm³
• Vapor Pressure: 1.27E-06mmHg at 25°C
• Refractive Index: 1.554
• PKA: -2.32±0.40(Predicted)
• CAS DataBase Reference: 1-Boc-4-phenylethynyl-piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-4-phenylethynyl-piperidine(669015-08-1)
• EPA Substance Registry System: 1-Boc-4-phenylethynyl-piperidine(669015-08-1)

Safety Data

• Hazardous Substances Data: 669015-08-1(Hazardous Substances Data)

Usage

Chemical class

Piperidine derivatives

Structure

Piperidine ring with a Boc protecting group at the 1-position and a phenylethynyl group at the 4-position

Boc group

tert-butoxycarbonyl protecting group

Phenylethynyl group

Ethynyl group attached to a phenyl ring

Application

Building block in organic synthesis

Industry

Pharmaceutical industry

Use

Preparation of bioactive molecules and pharmaceutical intermediates

Potential properties

Anticonvulsant and neuroprotective

Significance

Promising candidate for the development of novel therapeutic agents

InChI:InChI=1/C18H23NO2/c1-18(2,3)21-17(20)19-13-11-16(12-14-19)10-9-15-7-5-4-6-8-15/h4-8,16H,11-14H2,1-3H3

Upstream product

• 591-50-4 iodobenzene 
• 287192-97-6 4-ethynyl-piperidine-1-carboxylic acid tert-butyl ester 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 1872262-73-1 1-(tert-butyl) 4-(1,3-dioxoisoindolin-2-yl) piperidine-1,4-dicarboxylate 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 536-74-3 phenylacetylene 
• 28995-88-2 1-methyl-4-((phenylethynyl)sulfonyl)benzene 
• 637-44-5 phenylpropyolic acid 
• 5324-64-1 2-(benzenesulfonyl)ethynylbenzene 
• 88-67-5 2-Iodobenzoic acid 
• 131-62-4 1-hydroxy-1,2-benzodioxol-3-(1H)-one 

Downstream Products

• 654663-00-0 4-(phenylethynyl)piperidine 

Relevant articles and documents

Direct Photoexcitation of Ethynylbenziodoxolones: An Alternative to Photocatalysis for Alkynylation Reactions**

Ethynylbenziodoxolones (EBXs) are commonly used as radical traps in photocatalytic alkynylations. Herein, we report that aryl-substituted EBX reagents can be directly activated by visible light irradiation. They act as both oxidants and radical traps, alleviating the need for a photocatalyst in several reported EBX-mediated processes, including decarboxylative and deboronative alkynylations, the oxyalkynylation of enamides and the C?H alkynylation of THF. Furthermore, the method could be applied to the synthesis of alkynylated quaternary centers from tertiary alcohols via stable oxalate salts and from tertiary amines via aryl imines. A photocatalytic process using 4CzIPN as an organic dye was also developed for the deoxyalkynylation of oxalates.

Photoredox catalyzed C(sp3)[sbnd]C(sp) coupling of dihydropyridines and alkynylbenziodoxolones

A visible light mediated deformylative alkynylation of aldehydes is presented. Under photo irradiation, 1,4-dihydropyridine (DHP), derived from an aldehyde, generated a C(sp3)- radical which couples with an alkynylbenziodoxolone to generate an

Redox-Activated Amines in C(sp3)-C(sp) and C(sp3)-C(sp2) Bond Formation Enabled by Metal-Free Photoredox Catalysis

The amino group represents one of the most prevalent structural motifs in organic chemistry. Therefore, application of amines as alkylating agents in synthesis is highly compelling. Herein, we present a metal-free photoredox strategy for the formation of C(sp3)-C(sp) and C(sp3)-C(sp2) bonds from redox-activated primary amine derivatives. The developed reaction of 2,4,6-triphenylpyridinium salts with alkynyl p-tolylsulfones, leading to functionalized alkynes, is easily scalable and offers broad substrate scope, high chemoselectivity, and mild conditions. Its potential is also highlighted by diversification of complex molecular scaffolds. Additionally, the approach is also suitable for synthesis of (E)-alkenes from vinyl phenyl sulfones. Mechanistic studies contribute to the elucidation of unexpected differences in reactivity of primary and secondary alkyl substituted pyridinium salts.