3329-88-2

Basic information

• Product Name: 1-(p-Tosyloxy)-3-pentyne
• Synonyms: 1-(p-Tosyloxy)-3-pentyne;4-methylbenzenesulfonic acid pent-3-ynyl ester;pent-3-ynyl 4-methylbenzenesulfonate;pent-3-yn-1-yl 4-methylbenzenesulfonate
• CAS NO: 3329-88-2
• Molecular Formula: C₁₂H₁₄O₃S
• Molecular Weight: 238.30276
• Mol File: 3329-88-2.mol
• Article Data: 25

Chemical Properties

• Boiling Point: 372.3°Cat760mmHg
• Flash Point: 178.9°C
• Appearance: /
• Density: 1.172g/cm³
• Vapor Pressure: 2.08E-05mmHg at 25°C
• Refractive Index: 1.533
• CAS DataBase Reference: 1-(p-Tosyloxy)-3-pentyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(p-Tosyloxy)-3-pentyne(3329-88-2)
• EPA Substance Registry System: 1-(p-Tosyloxy)-3-pentyne(3329-88-2)

Safety Data

• Hazardous Substances Data: 3329-88-2(Hazardous Substances Data)

Usage

Functional groups

Alkyne, Tosylate (p-Tosyloxy) group

Use in organic synthesis

Reagent for the introduction of the alkyne functional group into molecules

Reactivity

Ability to undergo reaction with various nucleophiles to form new carbon-carbon bonds

Versatility

Tosylate group provides a good leaving group for substitution reactions

Applications

Construction of complex organic molecules, synthesis of pharmaceuticals and agrochemicals

Importance

Valuable tool in organic chemistry, important intermediate in the synthesis of various compounds

InChI:InChI=1/C12H14O3S/c1-3-4-5-10-15-16(13,14)12-8-6-11(2)7-9-12/h6-9H,5,10H2,1-2H3

Upstream product

• 54106-83-1 pent-3-ynyl triflate 
• 10229-10-4 pent-3-yn-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 73023-93-5 2-Methyl-4-oxo-3-pent-3-ynyl-cyclohex-2-enecarboxylic acid tert-butyl ester 
• 18719-27-2 5-bromo-pent-2-yne 
• 1517-15-3 2-methylcyclobutanone 
• 646-05-9 pent-1-en-3-yne 
• 53968-68-6 2-methylcyclobutenyl 2,2,2-trifluoroethyl ether 
• 97487-36-0 4-methylbut-3-yn-1-yl 2,2,2-trifluoroethyl ether 
• 73023-94-6 3-Methyl-2-pent-3-ynyl-cyclohex-2-enone 
• 765-43-5 Cyclopropyl methyl ketone 
• 10229-10-4 pent-3-yn-1-ol 
• 126988-84-9 3-pentynyltriphenylphosphonium p-toluenesulfonate 
• 165461-04-1 N-Benzyl-N-(pent-3-ynyl)-N-(prop-2-ynyl)amine 
• 59839-58-6 hex-3-yne-1,6-diyl-bis(4-methylbenzene sulfonate) 
• 1428156-79-9 N-cyclopropyl-N-(pent-3-yn-1-yl)benzamide 
• 1428156-83-5 1-benzoyl-4-methyl-2,3,7,7a-tetrahydro-1H-indol-5(6H)-one 

Relevant articles and documents

Synthesis of Morpholine-Based Analogues of (?)-Zampanolide and Their Biological Activity

We describe the convergent synthesis of three prototypical examples of a new class of analogues of the complex, cytotoxic marine macrolide (?)-zampanolide that incorporate an embedded N-substituted morpholine moiety in place of the natural tetrahydropyran ring. The final construction of the macrolactone core was based on a high-yielding intramolecular HWE olefination, while the hemiaminal-linked side chain was elaborated through a stereoselective, BINAL-H-mediated addition of (Z,E)-sorbamide to a macrocyclic aldehyde precursor. The synthesis of the common functionalized morpholine building block involved two consecutive epoxide openings with tosylamide and the product of the first opening reaction, respectively, as nucleophiles. Of the three morpholino-zampanolides investigated, the N-acetyl and the N-benzoyl derivatives both exhibited nanomolar antiproliferative activity, thus being essentially equipotent with the natural product. In contrast, the activity of the N-tosyl derivative was significantly reduced.

Total Synthesis of (-)-Mitrephorone A Enabled by Stereoselective Nitrile Oxide Cycloaddition and Tetrasubstituted Olefin Synthesis

A highly enantioselective and diastereoselective total synthesis of the diterpenoid (-)-mitrephorone A is presented. Key to the synthesis are stereocontrolled 1,4-semihydrogenation of a 1,3-diene to a tetrasubstituted double bond, enzyme-catalyzed malonat

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