764-37-4

Usage

Uses

Used in Flavor and Fragrance Industry:
OXY-3-PENTENE is used as a flavoring agent and fragrance ingredient for its grassy, green-fresh smell. It adds a natural and pleasant aroma to various products in this industry.
Used in Chemical Synthesis:
OXY-3-PENTENE is used as a building block for the synthesis of related esters and odor standards. Its unique structure allows for the creation of various compounds with different applications in the chemical industry.

InChI:InChI=1/C5H10O/c1-2-3-4-5-6/h2-3,6H,4-5H2,1H3/b3-2+

Upstream product

• 818-58-6 methyl (E)-pent-3-enoate 
• 7515-52-8 1-cyclopropyl-1-ethanol acetate 
• 504-60-9 penta-1,3-diene 
• 1069-54-1 bis-(1,2-dimethylpropyl)borane 
• 33698-87-2 (Z)-pent-3-enoic acid 
• 10229-10-4 pent-3-yn-1-ol 
• 65032-23-7 penta-2,3-dien-1-ol 
• 636-72-6 2-thiophenemethanol 
• 74379-22-9 (+/-)-2-hydroxymethyl-2,5-dihydrothiophene 
• 75-24-1 trimethylaluminum 
• 927-74-2 3-Butyn-1-ol 
• 60-29-7 diethyl ether 
• 30672-41-4 trans-3-chloro-2-methyltetrahydrofuran 
• 30672-41-4 cis-3-chloro-2-methyltetrahydrofuran 

Downstream Products

• 10229-10-4 pent-3-yn-1-ol 
• 71-41-0 pentan-1-ol 
• 110-62-3 pentanal 
• 764-38-5 (3Z)-pent-3-en-1-ol 
• 1641-49-2 α-trimethylsilylpentane 
• 3174-67-2 1,3-pentanediol 
• 1617-32-9 (E)-3-pentenoic acid 
• 1449467-79-1 (2R,3R)-5-(tert-butyl diphenylsilyloxy)pentane-2,3-diol 
• 1449467-80-4 tert-butyl diphenyl(2-((4R,5R)-2,2,5-trimethyl-1,3-dioxolan-4-yl)ethoxy)silane 
• 124070-55-9 (E)-tert-butyl (pent-3-enyloxy)diphenylsilane 
• 20086-87-7 (3S*)-hydroxy-(2R*)-methyltetrahydrofuran 
• 75272-39-8 N-((2S,3S)-1-benzyl-2-methylpyrrolidin-3-yl)-5-chloro-2-methoxy-4-(methylamino)benzamide 
• 1352347-71-7 C₁₃H₁₉NO₃S 
• 1337862-77-7 (2S,3S)-3-azido-1-benzyl-2-methylpyrrolidine 

Relevant academic research and scientific papers

Unexpected formation of a trans-syn-fused linear triquinane from a trimethylenemethane (TMM)-diyl-mediated [2+3] cycloaddition reaction

trans-Fused triquinane: Intramolecular-trimethylenemethane-mediated [2+3] cycloaddition reaction of a highly congested substrate proceeded stepwise to produce highly strained triquinane structures along with tricyclo[5.3.1.0 2, 6]undecanes.

SOLVENT-CONTROLLED ADDITIONS OF ORGANOTITANIUM REAGENTS TO OLEFINIC DOUBLE BONDS

Under carefully chosen working conditions (solvent, temperature), methyltitanium reagents smoothly convert homoallyl alcohols having a terminal double-bond into (E)-3-penten-1-ols whereas non-terminal 3-alken-1-ols afford 4-methyl-branched derivatives with configurational inversion of the chain (Z -> E; E -> Z), stereoselectivities being better than 99percent.

Alkyne Aminopalladation/Heck and Suzuki Cascades: An Approach to Tetrasubstituted Enamines

Alkyne aminopalladation reactions starting from tosylamides are reported. The emerging vinylic Pd species are converted either in an intramolecular Heck reaction with olefinic units or in an intermolecular Suzuki reaction by using boronic acids exhibiting broad functional group tolerance. Tetra(hetero)substituted tosylated enamines are obtained in a simple one-pot process.

Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3

Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.

Method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing (9Z, 12E)-9,12-tetradecadien-1-ol acetate. According to the method, malonic acid and 9-bromo-1-nonyl alcohol are used as two starting raw materials. The method comprises the following steps: carrying out a Knoevenagel condensation reaction on malonic acid and propionaldehyde inthe presence of piperidine acetate to generate (E)-3-pentenoic acid, then carrying out lithium aluminum hydride reduction to obtain (E)-3-penten-1-ol, carrying out bromination reaction, and refluxingwith triphenylphosphine in acetonitrile to obtain (E)-3-pentenyltriphenylphosphine bromide; carrying out a PCC oxidation reaction on 9-bromo-1-nonanol to obtain 9-bromononanal, and then reacting the 9-bromononanal with potassium acetate to obtain 9-acetoxynonanal; and finally, carrying out a Wittig reaction on (E)-3-pentenyltriphenylphosphine bromide and 9-acetoxynonanal so as to obtain (9Z, 12E)-9,12-tetradecadien-1-ol acetate. An E-type double bond is constructed by utilizing the Knoevenagel condensation reaction of malonic acid and propionaldehyde, and the method has the advantages of mildreaction conditions, environmental friendliness, simple synthetic route and the like.

Dynamic ?-Bonding of Imidazolyl Substituent in a Formally 16-Electron Cp Ru(2-P, N)+ Catalyst Allows Dramatic Rate Increases in (E)-Selective Monoisomerization of Alkenes

Alkene isomerization can be an atom-economical approach to generating a wide range of alkene intermediates for synthesis, but fully equilibrated mixtures of disubstituted internal alkenes typically contain significant amounts of the positional as well as geometric (E and Z) isomers. Most classical catalyst systems for alkene isomerization struggle to kinetically control either positional or E/Z isomerism. We report coordinatively unsaturated, formally 16-electron Cp Ru catalyst 5, which facilitates simultaneous regio- A nd stereoselective isomerization of linear 1-alkenes to their internal analogues, providing consistent yields of (E)-2-alkenes greater than 95%. Because nitrile-free catalyst 5 is more than 400 times faster than previously published nitrile-containing analogues 2 + 2a, very reasonable 0.1-0.5 mol % loadings of 5 complete ambient-temperature reactions within 15 min to 4 h. UV-vis, NMR, and computational studies depict the imidazolyl fragment on the phosphine as a hemilabile, four-electron donor in 2-P,N coordination. For the first time, we show direct experimental evidence that the PN ligand has accepted a proton from the substrate by characterizing the intermediate Cp Ru[??3-allyl][1-P)P-N+H], which highlights the essential role of the bifunctional ligand in promoting rapid and selective alkene isomerizations. Moreover, kinetic studies and computations reveal the role of alkene binding in selectivity of unsaturated catalyst 5.

Catalyst versus Substrate Control of Forming (E)-2-Alkenes from 1-Alkenes Using Bifunctional Ruthenium Catalysts

Here we examine in detail two catalysts for their ability to selectively convert 1-alkenes to (E)-2-alkenes while limiting overisomerization to 3- or 4-alkenes. Catalysts 1 and 3 are composed of the cations CpRu(κ2-PN)(CH3CN)+ and Cp?Ru(κ2-PN)+, respectively (where PN is a bifunctional phosphine ligand), and the anion PF6-. Kinetic modeling of the reactions of six substrates with 1 and 3 generated first- and second-order rate constants k1 and k2 (and k3 when applicable) that represent the rates of reaction for conversion of 1-alkene to (E)-2-alkene (k1), (E)-2-alkene to (E)-3-alkene (k2), and so on. The k1:k2 ratios were calculated to produce a measure of selectivity for each catalyst toward monoisomerization with each substrate. The k1:k2 values for 1 with the six substrates range from 32 to 132. The k1:k2 values for 3 are significantly more substrate-dependent, ranging from 192 to 62 000 for all of the substrates except 5-hexen-2-one, for which the k1:k2 value was only 4.7. Comparison of the ratios for 1 and 3 for each substrate shows a 6-12-fold greater selectivity using 3 on the three linear substrates as well as a >230-fold increase for 5-methylhex-1-ene and a 44-fold increase for a silyl-protected 4-penten-1-ol substrate, which are branched three and five atoms away from the alkene, respectively. The substrate 5-hexen-2-one is unique in that 1 was more selective than 3; NMR analysis suggested that chelation of the carbonyl oxygen can facilitate overisomerization. This work highlights the need for catalyst developers to report results for catalyzed reactions at different time points and shows that one needs to consider not only the catalyst rate but also the duration over which a desired product (here the (E)-2-alkene) remains intact, where 3 is generally superior to 1 for the title reaction.

Regioselective Epoxidations by Cytochrome P450 3A4 Using a Theobromine Chemical Auxiliary to Predictably Produce N-Protected β- or γ-Amino Epoxides

N-Protected β- and γ-amino epoxides are useful chiral synthons. We report here that the enzyme cytochrome P450 3A4 can catalyze the formation of such compounds in a regio- and stereoselective manner, even in the presence of multiple double bonds or aromatic substituents. To this end, the theobromine chemical auxiliary is used not only to control the selectivity of the enzyme, but also as a masked amine, and to facilitate product recovery. Theobromine predictably directed epoxidation at the double bond of the fourth carbon from the theobromine group. Unlike with most catalysts, the selectivity did not depend on electronic or steric factors but rather on the position of the olefin relative to the theobromine group. (Figure presented.).

Terminal alkene monoisomerization catalysts and methods

The invention provides novel catalysts and methods of using catalysts for controlling the position of a double bond and cis/trans-selectivity in isomerization of terminal alkenes to their 2-isomers. Catalysts such as (pentamethylcyclopentadienyl)Ru formulas 1 and 3 having a bifunctional phosphine can be used in the methods. A catalyst loading of 1 mol % of formulas 1+3 can be employed for the production of (E)-2-alkenes at 40-70° C.; lower temperatures can be used with higher catalyst loading. Acetonitrile-free catalysts can be used at lower loadings, room temperature, and in less than a day to accomplish the same results as catalysts 1+3. The novel catalyst systems minimize thermodynamic equilibration of alkene isomers, so that the trans-2-alkenes of both non-functionalized and functionalized alkenes can be generated.

A 2-methyl-3-tetrahydrofuran thiol acetate method for preparing trans isomer

The invention relates to a simple preparation method for a 2-methyl-3-tetrahydrofuranthiol acetate cis-trans-isomer which has the structural formula as shown in the specification. The simple preparation method comprises the following steps: propionaldehyde and propandioic acid are subjected to condensation through Knoevenagel to obtain (E)-3-pentenoic acid, the (E)-3-pentenoic acid is reduced through lithium aluminum hydride to obtain (E)-3-pentene-1-alcohol, and then the (E)-3-pentene-1- alcohol reacts with methylsulfonyl chloride to obtain (E)-3-pentene-1-alcohol methanesulfonate, wherein the three-step overall reaction yield is 24%; (E)-3-pentene-1-alcohol methanesulfonate is oxidized with hydrogen peroxide and methanoic acid, and are cyclizated under the alkaline condition to obtain trans-2- methyl-3-hydroxytetrahydrofuran, and hydroxyl is transformed into methanesulfonate which reacts with thioacetic acid to obtain cis-2-methyl-3-tetrahydrofuranthiol acetate, wherein the three-step overall reaction yield is 61%; (E)-3-pentene-1-alcohol methanesulfonate is oxidized with potassium permanganate to obtain cis-2-methyl-3-hydroxytetrahydrofuran, and hydroxyl is transformed into methanesulfonate which reacts with thioacetic acid to obtain trans-2-methyl-3-tetrahydrofuranthiol acetate, wherein the three-step overall reaction yield is 63%.