92666-05-2

Basic information

• Product Name: 1-(p-Tosyloxy)-2-pentyne
• Synonyms: 1-(p-Tosyloxy)-2-pentyne
• CAS NO: 92666-05-2
• Molecular Formula: C₁₂H₁₄O₃S
• Molecular Weight: 238.30276
• Mol File: 92666-05-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-(p-Tosyloxy)-2-pentyne(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(p-Tosyloxy)-2-pentyne(92666-05-2)
• EPA Substance Registry System: 1-(p-Tosyloxy)-2-pentyne(92666-05-2)

Safety Data

• Hazardous Substances Data: 92666-05-2(Hazardous Substances Data)

Upstream product

• 6261-22-9 pent-2-yn-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 1041847-77-1 [NMe₂(2-pentynyl)(CH=C(CH₃)2)][OTS] 
• 1558-79-8 2,5-octadiynyl bromide 
• 34498-25-4 1-bromo-2,5,8-undecatriyne 
• 5871-10-3 2,5,8,11-tetradecatetrayne-1-ol 
• 5871-06-7 1-bromotetradeca-2,5,8,11-tetrayne 
• 72561-88-7 (Z,Z,Z)-3,6,9-Octadecatriene 
• 90780-55-5 (±)-(4Z,8E,10Z,13Z,16Z,19Z)-7-hydroxydocosa-4,8,10,13,16,19-hexaenoic acid 
• 67548-36-1 (2E,5Z)-Octa-2,5-dien-1-ol 
• 194721-53-4 1-tosyloxy-2,5,8-undecatriyne 
• 35378-82-6 2,5,8-undecatriyne-1-ol 
• 282720-95-0 N-[2-(3-methoxy-4-pent-2-ynyloxy-phenyl)-ethyl]-formamide 
• 172659-63-1 1-(2-Benzyl-1-phenyl-hex-3-yne-2-sulfonyl)-propan-2-one 
• 172659-75-5 C₂₀H₂₂O₂S 
• 104188-11-6 (4Z,7Z)-4,7-decadien-1-ol 

Relevant articles and documents

Enantioselective Synthesis of 7(S)-Hydroxydocosahexaenoic Acid, a Possible Endogenous Ligand for PPARα

We report the first total synthesis of the polyunsaturated fatty acid 7-hydroxydocosahexaenoic acid (7-HDHA) in racemic form and the enantioselective synthesis of 7-(S)-HDHA. Both syntheses follow a convergent approach that unites the C1-C9 and C10-C22 fragments using Sonogashira coupling and Boland reduction as key steps. These syntheses enabled the unambiguous characterization of this natural product for the first time and helped establish 7(S)-HDHA as a possible endogenous ligand for peroxisome proliferator-activated receptor alpha.

A Modular, Enantioselective Synthesis of Resolvins D3, E1, and Hybrids

Resolvins D3 and E1 are important signaling molecules in the resolution of inflammation. Here, we report a convergent and flexible strategy to prepare these natural products using Hiyama-Denmark coupling of five- and six-membered cyclic alkenylsiloxanes to connect three resolvin fragments, and control the stereochemistry of the natural product (Z)-alkenes. The modular nature of this approach enables the synthesis of novel resolvin hybrids, opening up opportunities for more-extensive investigations of resolvin biology.

A tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - triene synthetic method of eighteen carbon (by machine translation)

The invention relates to a natural [...] pheromone component novel synthesis method, in particular relates to a tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene synthetic method, it has [...], is non-toxic and harmless, which belongs to the field of drug synthesis. The invention uses inexpensive and easily obtained a halopropynyl alcohol as the reaction of the starting material, in order to iodo reagent catalytic coupling reaction as a key step, after six-step reaction, smooth synthetic tea canker-worm pheromone (Z, Z, Z) - 3, 6, 9 - eighteen carbon triene, the operation is simple, low cost, easily obtained and cheap materials, mild reaction conditions, high yield, the large scale preparation. (by machine translation)

Total synthesis of (3Z,9Z,6S,7R) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadienes

(3Z,9Z,6S,7R)-6,7-epoxy-3,9-octadecadiene (1) and (3Z,9Z,6R,7S)-6,7-epoxy-3,9-octadecadiene (2) have been stereoselectively synthesized in eight steps from 2-pentyn-1-ol with an overall yield of 8%. The key steps involved the Sharpless asymmetric dihydrox

Catalytic Hydroalkylation of Allenes

We have developed a catalytic method for the hydroalkylation of allenes using alkyl triflates as electrophiles and silane as a hydride source. The reaction has an excellent substrate scope and is compatible with a wide range of functional groups, including esters, aryl halides, aryl boronic esters, sulfonamides, alkyl tosylates, and alkyl bromides. We found evidence for a reaction mechanism that involves unusual dinuclear copper ally complexes as catalytic intermediates. The unusual structure of these complexes provides a rationale for their unexpected reactivity.

METHODS FOR THE SYNTHESIS OF 13C LABELED DHA AND USE AS A REFERENCE STANDARD

A method for preparing 13C labeled docosahexaenoic acid (DHA) represented by Formula A: The method comprises the conversion of 2-pentyn-l-ol to 13C labeled DHA by reaction with propargyl alcohol, 13C labeled propargyl alco

METHOD FOR THE SYNTHESIS OF DHA

A method for preparing docosahexaenoic acid (DHA). The method comprises coupling a compound represented by Formula I with a compound represented by Formula II followed by partial hydrogenation to obtain a compound represented by Formula III. The compound represented by Formula III acts as a DHA precursor and thus can be hydrolysed to obtain DHA. Novel starting materials represented by Formula I and Formula II, and synthetic routes for preparing the same are also provided.

Aza cope rearrangement of propargyl enammonium cations catalyzed by a self-assembled "nanozyme"

The tetrahedral assembly [Ga4L6]12- [L = N,N-bis(2,3-dihydroxybenzoyl)-1,5-diaminonaphthalene) encapsulates a variety of cations, including propargyl enammonium cations capable of undergoing the aza Cope rearrangement. For propargyl enammonium substrates that are encapsulated in the [Ga4L6]12- assembly, rate accelerations by factors of up to 184 compared with the background reaction rate were observed. After rearrangement, the product iminium ion is released into solution and hydrolyzed, allowing for catalytic turnover. The activation parameters for the catalyzed and uncatalyzed reaction were determined, revealing that a decrease in the entropy of activation is responsible for the observed rate enhancements. The catalyzed reaction exhibits saturation kinetics: the rate data obeyed the Michaelis-Menten model of enzyme kinetics, and competitive inhibition using a nonreactive guest was demonstrated.

Sex pheromone of browntail moth, Euproctis chrysorrhea (L.): Synthesis and field deployment

The browntail moth, Euproctis chrysorrhea (L.), is native to Eurasia, where periodic outbreaks result in defoliation of forest, shade, and ornamental trees. In addition to the damage caused by defoliation, human contact with larval urticating hairs often

Antioxidant behaviour of thia fatty acids

Eight thia fatty acids and other sulfides have been studied as inhibitors of autoxidation of arachidonic acid. The inhibitors extend the lag phase of the oxidation, to varying degrees. A carboxyl group in the vicinity of the sulfur reduces the antioxidant activity, while unsaturated sulfides are more effective than their saturated analogues. The results are consistent with the sulfides acting to reduce fatty acid hydroperoxides, which otherwise accumulate during the early stages of reaction and propagate the free-radical oxidation process.