13249-60-0

Usage

InChI:InChI=1/C8H15Br/c1-3-4-5-6-7-8(2)9/h2-7H2,1H3

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 60-29-7 diethyl ether 
• 23708-48-7 pentamethylenebis(magnesium bromide) 
• 513-31-5 2-bromoallyl bromide 
• 693-25-4 n-pentylmagnesium bromide 
• 15719-55-8 trimethyl(oct-1-yn-1-yl)silane 
• 63883-62-5 octan-2-one 2,4,6-tri-isopropylbenzenesulphonylhydrazone 
• 629-05-0 n-octyne 
• 21948-46-9 1,2-dichlorooctane 
• 152212-49-2 1,2-dibromooctane 
• 109-73-9 N-butylamine 
• 1374350-55-6 2-octen-2-yl diphenyl phosphate 
• 87436-98-4 oct-1-en-2-yl diphenyl phosphate 
• 98747-02-5 oct-1-en-2-yl trifluoromethanesulfonate 

Downstream Products

• 629-05-0 n-octyne 
• 5698-49-7 2-phenyl-1-octene 
• 124573-37-1 1,4-Bis(1-hexylethenyl)benzene 
• 101720-90-5 1-(1-methylideneheptyl)naphthalene 
• 124573-36-0 1,2-Bis(1-hexylethenyl)benzene 
• 611-74-5 N,N-dimethylbenzamide 
• 6301-00-4 9-hexylindene 
• 43130-70-7 3-hexyl-1H-indene 
• 1599438-09-1 2-benzyl-2-hexylcyclopentanone 
• 1227189-20-9 N,N-bis(phenyl)oct-2-en-2-amine 
• 1227189-26-5 N,N-bis(4-fluorophenyl)oct-2-en-2-amine 
• 1227189-22-1 N,N-bis(4-methoxyphenyl)oct-2-en-2-amine 
• 1227189-24-3 N,N-bis(4-methylphenyl)oct-2-en-2-amine 
• 221676-20-6 <(1S,2S)-1-cyclohexyl-2-(methoxymethyl)oxy-3-buten-1-yloxy>(dimethyl)(1-octen-2-yl)silane 

Relevant academic research and scientific papers

Structure-Activity Relationships of Cyclopropene Compounds, Inhibitors of Pheromone Biosynthesis in Bombyx mori

According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C16 chain and the 11,12-position in a C14 or C18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E, 12Z)-10,12-hexadecadien-1-ol; sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 μg/gland, but other compounds at 1 μg/gland inhibited the conversion of [16,16,16-2H3]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C16 chain was the strongest (I50 = 0.016 μg/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-14C]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the Δ11-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Δ10,-12-desaturation by 11,12- and 13,14-methylene compounds.

Br?nsted Acid-Catalyzed Enantioselective Iodocycloetherification Enabled by Triphenylphosphine Selenide Cocatalysis

Enantioselective iodocycloetherifications can be conducted using sterically highly demanding BINOL-based phosphoric acid diesters as catalyst. To achieve highly enantioselective reactions, cocatalysis by triphenylphosphine selenide is necessary. With coca

Metal-free regioselective hydrobromination of alkynes through CH/CBr activation

A metal-free regioselective hydrobromination of alkynes has been developed to provide the Markovnikov-type vinyl bromides in good yields using dibromomethane/N,N-dimethylaniline as in-situ 'HBr' source. This protocol also represents an elegant example of the activation of sp2 CH and CBr bonds in one pot, in which 'HBr' is generated and transferred under mild metal-free conditions. D-incorporated experiments were employed to investigate the reaction mechanism and a plausible reaction path was proposed.

Iridium-catalyzed enantioselective hydrogenation of alkenylboronic esters

Choose the right ligand: An iridium complex derived from a phosphino-imidazoline ligand is a highly efficient catalyst for the asymmetric hydrogenation of terminal vinyl boronic esters (see scheme). On the other hand, trisubstituted alkenyl-boronates can

Ruthenium-catalyzed transformation of aryl and alkenyl triflates to halides

Aryl triflates were transformed to aryl bromides/iodides simply by treating them with LiBr/NaI and [Cp*Ru(MeCN)3]OTf. The ruthenium complex also catalyzed the transformation of alkenyl sulfonates and phosphates to alkenyl halides under mild conditions. Aryl and alkenyl triflates undergo oxidative addition to a ruthenium(II) complex to form η'1- arylruthenium and 1-ruthenacyclopropene intermediates, respectively, which are transformed to the corresponding halides.

α-Selective Ni-catalyzed hydroalumination of aryl- and alkyl-substituted terminal alkynes: Practical syntheses of internal vinyl aluminums, halides, or boronates

A method for Ni-catalyzed hydroalumination of terminal alkynes, leading to the formation of α-vinylaluminum isomers efficiently (>98% conv in 2-12 h) and with high selectivity (95% to >98% α), is described. Catalytic α-selective hydroalumination reactions proceed in the presence of a reagent (diisobutylaluminum hydride; dibal-H) and 3.0 mol % metal complex (Ni(dppp)Cl2) that are commercially available and inexpensive. Under the same conditions, but with Ni(PPh3)2Cl2, hydroalumination becomes highly β-selective, and, unlike uncatalyzed transformations with dibal-H, generates little or no alkynylaluminum byproducts. All hydrometalation reactions are reliable, operationally simple, and practical and afford an assortment of vinylaluminums that are otherwise not easily accessible. The derived α-vinyl halides and boronates can be synthesized through direct treatment with the appropriate electrophiles [e.g., Br 2 and methoxy(pinacolato)boron, respectively]. Ni-catalyzed hydroaluminations can be performed with as little as 0.1 mol % catalyst and on gram scale with equally high efficiency and selectivity.

Ruthenium-catalyzed transformation of alkenyl triflates to alkenyl halides

In the presence of a ruthenium catalyst, alkenyl triflates were found to be transformed to the corresponding bromides, chlorides and iodides simply by treatment with a lithium halide (1.2 equiv.). The Royal Society of Chemistry 2009.

Rh-catalyzed enantioselective hydrogenation of vinyl boronates for the construction of secondary boronic esters

Rh-catalyzed hydrogenation of prochiral vinyl boronates occurs in an enantioselective fashion in the presence of the chiral ligand Walphos 1. This transformation provides access to chiral secondary organoboronates that are not available from alkene hydrob

Fe(III) halides as effective catalysts in carbon-carbon bond formation: Synthesis of 1,5-dihalo-1,4-dienes, αβ-unsaturated ketones, and cyclic ethers

(Chemical Equation Presented). Iron(III) halides have proven to be excellent catalysts in the coupling of acetylenes and aldehydes. When terminal acetylenes were used the main products obtained were 1,5-dihalo-1,4-dienes with (E,Z)-stereochemistry contaminated in some cases with (E)-α,β- unsaturated ketones. The former carbonyl derivatives were the sole products isolated when nonterminal aromatic alkynes were used. When homopropargylic alcohols were used, a Prins-type cyclization occurred yielding 2-alkyl-4-halo-5,6-dihydro-2H-pyrans. In addition, anhydrous ferric halides are also shown to be excellent catalysts for the standard Prins cyclization with homoallylic alcohols. Isolation of an intermediate acetal, calculations, and alkyne hydration studies provide substantiation of a proposed mechanism.

Stable ethylene inhibiting compounds and methods for their preparation

A method to inhibit the ethylene response in plants with cyclopropene compounds by first generating stable cyclopropane precursor compounds and then converting these compounds to the gaseous cyclopropene antagonist compound by use of a reducing or nucleophilic agent.