18495-27-7

Usage

Uses

1. Used in the Synthesis of Pinolenic Acid:
1-BROMO-2-OCTYNE is used as a chemical intermediate for the synthesis of pinolenic acid, which is a unique fatty acid found in pine nuts. The application reason is its ability to facilitate the formation of pinolenic acid through a series of chemical reactions.
2. Used in the Preparation of Substituted Indoles:
1-BROMO-2-OCTYNE is also used in the preparation of substituted indoles through Rh-catalyzed amino-Claisen rearrangement. In this application, the compound serves as a key reactant to produce substituted indoles, which are important building blocks in the synthesis of various pharmaceuticals and biologically active compounds.
3. Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-BROMO-2-OCTYNE is used as a synthetic intermediate for the development of new drugs and therapeutic agents. The application reason is its potential to be transformed into various bioactive molecules through chemical reactions, contributing to the discovery of novel pharmaceutical compounds.
4. Used in Chemical Research and Development:
1-BROMO-2-OCTYNE is utilized in chemical research and development as a starting material for the synthesis of various organic compounds. The application reason is its unique chemical structure, which allows for a wide range of reactions and the creation of diverse chemical products.

Upstream product

• 53799-92-1 tetra-N-methyl-phosphorodiamidic acid oct-2-ynyl ester 
• 693-03-8 n-butyl magnesium bromide 
• 2219-66-1 1,4-dibromobut-2-yne 
• 54369-44-7 methanesulfonic acid oct-2-ynyl ester 
• 558-13-4 carbon tetrabromide 
• 20739-58-6 2-octyn-1-ol 
• 67-66-3 chloroform 
• 7789-60-8 phosphorus tribromide 
• 110-53-2 1-Bromopentane 
• 111-12-6 methyl 2-octynoate 
• 141493-78-9 1,1,2-tribromo-2-pentylcyclopropane 
• 13291-18-4 isopropenylmagnesium bromide 
• 57342-29-7 1-(p-tolylsulfonyloxy)oct-2-yne 
• 36602-98-9 2-(oct-2-yn-1-yloxy)tetrahydro-2H-pyran 

Downstream Products

• 56630-33-2 non-3-ynoic acid 
• 69754-58-1 (hydroxy-1 cyclohexyl)-3 octadiene-1,2 
• 83606-41-1 ((3Z,6Z)-dodeca-3,6-dien-1-yl)triphenylphosphonium bromide 
• 117417-17-1 3-phenylsulfonyl-5-undecyn-2-one 
• 217187-39-8 2-oct-2-ynylsulfanyl-phenol 
• 98814-47-2 16-chlorohexadeca-6,9-diyne 
• 4436-86-6 2-pentyl-butadienoic acid 
• 477199-27-2 (1R,3R,5S)-6,6-Dimethyl-3-oct-2-ynyl-bicyclo[3.1.1]heptan-2-one 
• 287201-65-4 (4-oct-2-ynyloxyphenylsulfanyl)acetic acid ethyl ester 
• 71030-39-2 (+/-)-5-HETE 
• 70968-99-9 (=/-)-5-hydroxy-6-trans-8,11,14,-cis-eicosatetraenoic acid methyl ester 
• 1191-85-1 eicosa-5,8,11,14-tetraynoic acid 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 506-26-3 all-cis-6,9,12-octadecatrienoic acid 

Relevant academic research and scientific papers

Total synthesis of leukotriene E4, a member of the SRS-A family

Leukotriene E4 and two analogues homo-LTE4 and nor-LTE4 have been prepared via the intermediate epoxides. The epoxides were formed by the coupling of a polyenyne sulfonium salt with the required aldehyde-ester in a biphasic reaction system employing aqueous sodium hydroxide as the base for the generation of the ylide. Reduction of the acetylene bonds yielded the desired polyene epoxides which on treatment with L-cysteine methyl ester gave a 1:1 mixture of diastereomers from which the 5S,6R isomers were separated.

Aliphatic sulfates released from Daphnia induce morphological defense of phytoplankton: Isolation and synthesis of kairomones

Six aliphatic sulfates, kairomones released from a crustacean Daphnia pulex induce morphological changes of phytoplankton Scenedesmus gutwinskii at ppb (10-9 g/mL) concentrations.

Rhodium-Catalyzed Asymmetric [2+2+2] Cycloaddition of 1,6-Enynes with Racemic Secondary Allylic Alcohols through Kinetic Resolution

It has been established that a cationic rhodium(I)/P-phos complex catalyzes the asymmetric [2+2+2] cycloaddition of 1,6-enynes with racemic secondary allylic alcohols to produce the corresponding chiral bicyclic cyclohexenes, possessing three stereogenic

Kinetics of the reaction of N,N-dimethylaniline with 1-bromoalk-2-ynes

Quaternization of N,N-dimethylaniline with propargyl bromide, 1-bromobut-2-yne, and 1-bromooct-2-yne were studied. It was shown that, with the lengthening chain of the substituent at the triple bond, the quaternization rate tends to increase.

Nanoporous gold catalyst for highly selective semihydrogenation of alkynes: Remarkable effect of amine additives

We report for the first time the highly selective semihydrogenation of alkynes using the unsupported nanoporous gold (AuNPore) as a catalyst and organosilanes with water as a hydrogen source. Under the optimized reaction conditions, the present semihydrogenation of various terminal- and internal-alkynes affords the corresponding alkenes in high chemical yields and excellent Z-selectivity without any over-reduced alkanes. The use of DMF as solvent, which generates amines in situ, or pyridine as an additive is crucial to suppress the association of hydrogen atoms on AuNPore to form H2 gas, which is unable to reduce alkynes on the unsupported gold catalysts. The AuNPore catalyst can be readily recovered and reused without any loss of catalytic activity. In addition, the SEM and TEM characterization of nanoporosity show that the AuNPore catalyst has a bicontinuous 3D structure and a high density of atomic steps and kinks on ligament surfaces, which should be one of the important origins of catalytic activity.

Investigating inner-sphere reorganization via secondary kinetic isotope effects in the C-H cleavage reaction catalyzed by soybean lipoxygenase: Tunneling in the substrate backbone as well as the transferred hydrogen

This work describes the application of NMR to the measurement of secondary deuterium (2° 2H) and carbon-13 (13C) kinetic isotope effects (KIEs) at positions 9-13 within the substrate linoleic acid (LA) of soybean lipoxygenase-1. The KIEs have been measured using LA labeled with either protium (11,11- h2-LA) or deuterium (11,11-d2-LA) at the reactive C11 position, which has been previously shown to yield a primary deuterium isotope effect of ca. 80. The conditions of measurement yield the intrinsic 2° 2H and 13C KIEs on kcat/Km directly for 11,11-d2-LA, whereas the values for the 2° 2H KIEs for 11,11-h2-LA are obtained after correction for a kinetic commitment. The pattern of the resulting 2° 2H and 13C isotope effects reveals values that lie far above those predicted from changes in local force constants. Additionally, many of the experimental values cannot be modeled by electronic effects, torsional strain, or the simple inclusion of a tunneling correction to the rate. Although previous studies have shown the importance of extensive tunneling for cleavage of the primary hydrogen at C11 of LA, the present findings can only be interpreted by extending the conclusion of nonclassical behavior to the secondary hydrogens and carbons that flank the position undergoing C-H bond cleavage. A quantum mechanical method introduced by Buhks et al. [J. Phys. Chem. 1981, 85, 3763] to model the inner-sphere reorganization that accompanies electron transfer has been shown to be able to reproduce the scale of the 2° 2H KIEs.

Synthesis of carbazoles by gold(I)-catalyzed carbocyclization of 2-(enynyl)indoles

A new synthetic protocol for carbazoles through gold(I)-catalyzed intramolecular hydroarylation of (Z)-2-(enynyl)indoles was achieved in good yields. The requisite (Z)-2-(enynyl)indoles were synthesized stereoselectively by trimethylgallium-promoted, Z-selective Wittig olefination of N-alkylindole-2-carboxaldehydes with propargyl ylides. Substrates possessing both alkyl as well as aromatic groups are well tolerated under these reaction conditions. Georg Thieme Verlag Stuttgart.

Structurally and stereochemically diverse tetrahydropyran synthesis through oxidative C-H bond activation

Simple as pyran: Vinylsilane-substituted tetrahydropyrans, readily accessed through the oxidative C-H bond functionalization of silylallylic or propargylic ethers (see scheme; DDQ = 2,3-dichloro5,6-dicyano-l,4-benzoquinone), are versatile substrates for a wide range of functional group interconversions and stereocontrolled additions. These processes have applications in convergent target- or diversity-oriented synthesis strategies. (Chemical equation presented)

Synthesis of linoleic acids combinatorially labeled at the vinylic positions as substrates for lipoxygenases

Mammalian lipoxygenases have been implicated in a number of inflammation-related human diseases. Soybean lipoxygenase-1 is the archetypical example of known lipoxygenases. Here we report the synthesis of linoleic acid and (11,11)-d2-linoleic acid which are combinatorially labeled at the vinylic positions (9, 10, 12, and 13). Combinatorial labeling schemes allow for the simultaneous determination of KIEs in enzymatic reactions using NMR. Substrates are, thus, available as probes of detailed mechanism in kinetic isotope effect (KIE) studies of lipoxygenases.

Synthesis and biological evaluation of several structural analogs of 2-arachidonoylglycerol, an endogenous cannabinoid receptor ligand

2-Arachidonoylglycerol (2-AG (1)) is an endogenous ligand for the cannabinoid receptors (CB1 and CB2). There is growing evidence that 2-arachidonoylglycerol plays important physiological and pathophysiological roles in various mammalian tissues and cells,