27593-19-7

Usage

Uses

Used in Pharmaceutical Industry:
1-Octyn-3-one is used as a synthetic intermediate for the production of pharmaceuticals, contributing to the development of new drugs and medicines due to its unique structure and reactivity.
Used in Pesticide Industry:
In the realm of agriculture, 1-Octyn-3-one is utilized as a component in the synthesis of pesticides, playing a role in creating effective solutions for pest control.
Used in Organic Chemistry Research:
1-Octyn-3-one is employed as a research tool in organic chemistry, facilitating experimental studies and exploration of new chemical reactions and mechanisms.
Used in Development of Novel Materials:
Recognized as a potential building block, 1-Octyn-3-one is used in the development of innovative materials and bioactive compounds, indicating its broad applicability in material science.

Upstream product

• 818-72-4 1-Octyn-3-ol 
• 142-61-0 Hexanoyl chloride 
• 4301-14-8 acetylenemagnesium bromide 
• 629-05-0 n-octyne 
• 66-25-1 hexanal 
• 17962-52-6 1-(trimethylsilyl)-1,2-octadiene 

Downstream Products

• 32556-71-1 1-octyn-3-ol 
• 72443-72-2 (R)-1-((R)-6-Benzyloxy-2,5,7,8-tetramethyl-chroman-2-yl)-pent-3-yn-2-ol 
• 136730-69-3 (Z,Z)-bis(3-oxo-1-octenyl)sulfide 
• 126959-20-4 2,4,6-tri(2-oxoheptyl)-1,3,5-trithiane 
• 136730-72-8 (Z,E)-bis(3-oxo-1-octenyl)sulfide 
• 136757-16-9 (E,E)-bis(3-oxo-1-octenyl)sulfide 
• 108161-47-3 (Z)-1-Bromo-oct-1-en-3-one 
• 52418-89-0 (E)-1-bromo-1-octen-3-one 
• 39178-64-8 (E)-1-iodo-1-octen-3-one 
• 109572-55-6 (E)-2-(Hydroxy-phenyl-methyl)-1-iodo-oct-1-en-3-one 
• 109572-44-3 (Z)-2-(Hydroxy-phenyl-methyl)-1-iodo-oct-1-en-3-one 
• 109572-54-5 (E)-1-Chloro-2-(hydroxy-phenyl-methyl)-oct-1-en-3-one 
• 109572-45-4 2-Hydroxy-3-[1-iodo-meth-(Z)-ylidene]-nonan-4-one 
• 109572-47-6 2-Hydroxy-3-[1-iodo-meth-(E)-ylidene]-nonan-4-one 

Relevant academic research and scientific papers

Regio- and Stereoselective Alkylation of a Pyrrolidinic System: Structural and Conformational Studies by High Field NMR Techniques

A new merocyanine was prepared by addition of the pyrrolidine enamine of N-ethoxycarbonylpyrrolidine-3-one to 1-octyne-3-one.This addition was regioselective (with an unexpected C-4 alkylation of the pyrrolidinone-3-enamine) and stereospecific (exclusively trans addition to the triple bond).The structure and conformational equilibrium were studied by high resolution proton magnetic resonance (NOE and variable temperature effects).Activation parameters ΔH*, ΔS* and ΔG* are given, and the behaviour on protonation examined.

Isoketals form cytotoxic phosphatidylethanolamine adducts in cells

Levuglandins and their stereo- and regio-isomers (termed isolevuglandins or isoketals) are γ-ketoaldehydes (IsoK) that rapidly react with lysines to form stable protein adducts. IsoK protein adduct levels increase in several pathological conditions including cardiovascular disease. IsoKs can induce ion channel dysfunction and cell death, potentially by adducting to cellular proteins. However, IsoKs also adduct to phosphatidylethanolamine (PE) in vitro, and whether PE adducts form in cells or contribute to the effects of IsoKs is unknown. When radiolabeled IsoK was added to HEK293 cells, 40% of the radiolabel extracted into the chloroform lower phase suggesting the possible formation of PE adducts. We therefore developed methods to measure IsoK-PE adducts in cells. IsoK-PE was quantified by LC/MS/MS after hydrolysis to IsoK-ethanolamine by Streptomyces chromofuscus phospholipase D. In HEK293 and human umbilical vein endothelial cells (HUVEC), IsoK dose-dependently increased PE adduct concentrations to a greater extent than protein adduct. To test the biological significance of IsoK-PE formation, we treated HUVEC with IsoK-PE. IsoK-PE dose dependently induced cytotoxicity (LC50 2.2 μM). These results indicate that cellular PE is a significant target of IsoKs, and that formation of PE adducts may mediate some of the biological effects of IsoKs relevant to disease. Copyright

Chemoselective photocatalytic oxidation of alcohols to aldehydes and ketones by nitromethane on titanium dioxide under violet 400 nm LED light irradiation

In this study, for the first time, nitroalkanes, especially nitromethane, have been used as electron acceptors for the highly chemoselective oxidation of alcohols in the presence of a TiO2 photocatalyst under 400 nm LED irradiation. The reactions showed excellent selectivity for the production of aldehydes. Interestingly, aldehydes such as benzaldehyde and p-methoxybenzaldehyde are stable under the reaction conditions. In the case of the use of 2-nitropropane and 2-methyl-2-nitropropane, the product imine, which is the result of the reaction of the aldehyde with aliphatic amine, is also obtained.

Aerobic oxidation of alcohols catalyzed by in situ generated gold nanoparticles inside the channels of periodic mesoporous organosilica with ionic liquid framework

In situ generated gold nanoparticles inside the nanospaces of periodic mesoporous organosilica with an imidazolium framework (Au?PMO-IL) were found to be highly active, selective, and reusable catalysts for the aerobic oxidation of activated and nonactivated alcohols under mild reaction conditions. The catalyst was characterized by nitrogen adsorption-desorption measurement, thermogravimetric analysis (TGA), transmission electron microscopy (TEM), elemental analysis (EA), diffuse reflectance infrared Fourier transform spectroscopy (DRIFT), X-ray photoelectron spectroscopy (XPS), and inductively coupled plasma atomic emission spectroscopy (ICP-AES). The catalyst exhibited excellent catalytic activity in the presence of either Cs2CO3 (35 °C) or K2CO3 (60 °C) as reaction bases in toluene as a reaction solvent. Under both reaction conditions, various types of alcohols (up to 35 examples) including activated benzylic, primary and secondary aliphatic, heterocyclic, and challenging cyclic aliphatic alcohols converted to the expected carbonyl compounds in good to excellent yields and selectivity. The catalyst was also recovered and reused for at least seven reaction cycles. Data from three independent leaching tests indicated that amounts of leached gold particles were negligible (0.2 ppm). It is believed that the combination of bridged imidazolium groups and confined nanospaces of PMO-IL might be a major reason explaining the remarkable stabilization and homogeneous distribution of in situ generated gold nanoparticles, thus resulting in the highly active and recyclable catalyst system.

1,1-Diphosphines and divinylphosphines via base catalyzed hydrophosphination

A catalytic hydrophosphination route to 1,1-diphosphines is yet to be reported: these narrow bite angle pro-ligands have been used to great effect as ligands in homogeneous catalysis. We herein demonstrate that terminal alkynes readily undergo double hydrophosphination with HPPh2 and catalytic potassium hexamethyldisilazane (KHMDS) to generate 1,1-diphosphines. A change to H2PPh leads to the formation of P,P-divinyl phosphines.

Synergistic catalysis within TEMPO-functionalized periodic mesoporous organosilica with bridge imidazolium groups in the aerobic oxidation of alcohols

Anchoring 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO) within the nanospaces of a periodic mesoporous organosilica with bridged imidazolium groups led to an unprecedented powerful bifunctional catalyst (TEMPO@PMO-IL-Br), which showed enhanced activity in the metal-free aerobic oxidation of alcohols. The catalyst and its precursors were characterized by N2 adsorption-desorption analysis, transmission electron microscopy (TEM), small angle X-ray scattering (SAXS), thermal gravimetric analysis (TGA), diffuse reflectance infrared Fourier transform spectroscopy (DRIFT), solid state electron paramagnetic resonance (EPR) spectroscopy, elemental analysis, transmission electron microscopy (TEM) and high resolution TEM. It was clearly found that the catalytic activity of SBA-15-functionalized TEMPO (TEMPO@SBA-15) not bearing IL, TEMPO@PMO-IL-Cl, PMO-IL-AMP, or individual catalytic functionalities (PMO-IL/TEMPO@SBA-15) was inferior as compared with those obtained from TEMPO@PMO-IL-Br in the metal-free aerobic oxidation of benzyl alcohol, suggesting the critical role of co-supported TEMPO and imidazolium bromide in obtaining high catalytic activity in the described catalyst system. Our observation clearly points to the fact that the combination of imidazolium bromide units in close proximity to TEMPO moieties in the nanospaces of TEMPO@PMO-IL-Br might be indeed one of the key factors explaining the enhanced catalytic activity observed for this catalyst in the oxidation of benzyl alcohol, possibly through a synergistic catalysis relay pathway. A proposed model was suggested for the observed synergistic effect.

A propargyl alcohol oxidation system acetylenic ketone method

The invention provides a method for preparing acetylenic ketone through oxidizing propargyl alcohol. The method comprises the following steps: in a liquid phase, taking 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) as the catalyst, nitric acid as the co-catalyst, and oxygen gas as the oxidant, and oxidizing propargyl alcohol in an organic solvent so as to produce acetylenic ketone. The method has the advantages of mild conditions, convenient operation, no metal, and little pollution, and is a green and environment-friendly novel method for preparing ketone through oxidizing alcohol with a non-metal catalyst.

Styrene as 4π-Component in Zn(II)-Catalyzed Intermolecular Diels-Alder/Ene Tandem Reaction

A mild Zn-catalyzed intermolecular Diels-Alder/ene tandem reaction with styrene as a 4π-component is reported. A variety of dihydronaphthalene products could be prepared in moderate to good yields. Moreover, a combination of DFT calculations and experiments was performed to further understand the mechanism of this unique tandem reaction.

SBA-15-Functionalized 3-Oxo-ABNO as Recyclable Catalyst for Aerobic Oxidation of Alcohols under Metal-Free Conditions

The nitroxyl radical 3-oxo-9-azabicyclo [3.3.1]nonane-N-oxyl (3-oxo-ABNO) has been prepared using a simple protocol. This organocatalyst is found to be an efficient catalyst for the aerobic oxidation of a wide variety of alcohols under metal-free conditions. In addition, the preparation and characterization of a supported version of 3-oxo-ABNO on ordered mesoporous silica SBA-15 (SABNO) is described for the first time. The catalyst has been characterized using several techniques including simultaneous thermal analysis (STA), transmission electron microscopy (TEM), and nitrogen sorption analysis. This catalyst exhibits catalytic performance comparable to its homogeneous analogue and much superior catalytic activity in comparison with (2,2,6,6-tetramethylpiperidin-1-yl)oxy (TEMPO) for the aerobic oxidation of almost the same range of alcohols under identical reaction conditions. It is also found that SABNO can be conveniently recovered and reused at least 12 times without significant effect on its catalytic efficiency.

A simple and efficient method for mild and selective oxidation of propargylic alcohols using TEMPO and calcium hypochlorite

Oxidation of propargylic alcohols to the corresponding aldehydes and ketones was achieved at room temperature using 2,2,6,6-tetramethylpiperidine-1- oxyl (TEMPO) and calcium hypochlorite (Ca(OCl)2). Propargylic diols yielded corresponding dialdehydes as the product. This system was found to be very efficient for both the electron donating and electron withdrawing groups such as methoxy and nitro substituted alcohols, respectively. This method does not require any additives and demonstrates the controlled, selective oxidation of propargylic alcohols affording up to 97% isolated yield. The Royal Society of Chemistry 2013.