72206-25-8

Upstream product

• 638-29-9 n-valeryl chloride 
• 110-62-3 pentanal 
• 1016669-36-5 1-phenylhept-2-ynyl pivalate 
• 73922-80-2 1-phenylhept-2-yn-1-ol 
• 536-74-3 phenylacetylene 
• 13146-23-1 copper(I) phenylacetylenide 
• 22342-18-3 1-morpholinopentan-1-one 
• 110-53-2 1-Bromopentane 
• 14374-45-9 1-heptynylbenzene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 4440-01-1 lithium phenylacetylide 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 
• 693-02-7 hex-1-yne 

Downstream Products

• 261506-10-9 (-)-1-phenyl-hept-1-yn-3-ol 
• 1152672-30-4 1-(2-tert-butyl-3,5-diphenyl-2,3-dihydro-isoxazol-4-yl)-pentan-1-one 
• 1103532-33-7 3-butyl-2-methyl-5-phenylpent-2-en-4-ynoic acid 
• 72206-30-5 1-formyl-2-phenyl-2-(1-hexynyl)cyclopropane 
• 72206-37-2 (Z)-2-butylidene-4-phenyl-2,5-dihydrooxepin 
• 882182-98-1 5-butyl-3,3-difluoro-2-methoxy-2-phenyl-2,3-dihydro-furan 
• 882182-87-8 1-(3,3-difluoro-2-phenyl-cycloprop-1-enyl)-pentan-1-one 
• 138298-43-8 (3S)-1-phenylheptan-3-ol 

Relevant academic research and scientific papers

Copper-catalyzed method for preparing aldehyde or ketone compound by oxidizing alcohol with oxygen as oxidizing agent and application

The invention discloses a copper-catalyzed method for preparing an aldehyde or ketone compound by oxidizing alcohol with oxygen as an oxidizing agent. Reaction is performed in an organic solvent for 4-48 hours at room temperature by using copper salt and nitroxide free radicals as catalysts and oxygen or air as an oxidizing agent to efficiently oxidize an alcohol compound into the corresponding aldehyde or ketone compound. The method is simple to operate, free of chlorides corrosive to equipment, available in raw materials and reagents, mild in reaction conditions, wide in substrate universality, good in functional group compatibility, convenient in separation and purification, environmentally friendly in the whole process and free of pollution, and is a method suitable for industrial production.

General Synthesis of α-Alkyl Ynones from Morpholine Amides and 1-Copper(I) Alkynes Promoted by Triflic Anhydride

The first general method for the synthesis of α-alkyl ynones was developed based on the strategy of electrophilic activation of amides. Its distinctive advantages are attributed to the use of air-stable "bare"1-copper(I) alkyne as a mild nucleophile witho

Pd-Catalyzed Cross-Coupling of Terminal Alkynes with Chromium(0) Fischer Carbene Complexes

Alkyl chromium(0) carbene complexes typically undergo cycloadditions with alkynes to afford carbo- or heterocyclic compounds. In the presence of Pd catalyst, it is demonstrated that a traditional cycloaddition pathway is completely altered: instead of cyc

MnO2/TBHP: A Versatile and User-Friendly Combination of Reagents for the Oxidation of Allylic and Benzylic Methylene Functional Groups

In the presence of activated MnO2, tert-butyl hydroperoxide (TBHP) in CH2Cl2 is able to oxidize the allylic and benzylic methylene groups of different classes of compounds. I describe a one-pot oxidation protocol based on two sequential steps. In the first step, carried out at low temperature, MnO2 catalyses the oxidation of the methylene group. This is followed by a second step where reaction temperature is increased, allowing MnO2 both to catalyse the decomposition of unreacted TBHP and to oxidize allylic alcohols that could possibly be formed. The proposed oxidation procedure is generally applicable, although its efficiency, regioselectivity, and chemoselectivity are strongly dependent on the structure of the substrate. A simple and user-friendly synthetic procedure for the oxidation of allylic and benzylic methylene groups to the corresponding conjugated carbonyl derivatives is described. The proposed oxidation protocol is based on the combined use of MnO2 and tert-butyl hydroperoxide, and is generally applicable.

Dehydrogenative Meyer-Schuster-like rearrangement: A gold-catalyzed reaction generating an alkyne

Easily accessible propargylic esters are converted to the inverted alkynyl ketones in an oxidative gold-catalyzed reaction. Gagosz's catalyst in combination with PhI(OAc)2 is the best system for this conversion and 18 examples with yields up to 80 % are reported. The results indicate that the triple bond in the product is formed by elimination from a vinylgold intermediate. In a formal sense the new conversion overall is a dehydrogenative Meyer-Schuster rearrangement. It takes alkynes: Propargyl esters can be converted into alkynyl ketones by a new oxidative gold-catalyzed reaction. The best catalyst system is Ph3PAuCl/AgNTf2 in combination with the oxidant PhI(OAc)2. The yields are as high as 80 % and the reaction can be conducted in the presence of air. Copyright

Easy preparation of 1,4,5-trisubstituted 5-(2-alkoxy-1,2-dioxoethyl)-1,2,3- triazoles by chemoselective trapping of copper(I)-carbon bond with alkoxalyl chloride

We found that alkoxalyl chloride (ClCOCO2R) did not carry out an acylation on 1-copper(I) alkyne in solvent without additives, but chemoselectively on 5-copper(I) 1,2,3-triazole (an intermediate in cycloaddition of 1-copper(I) alkyne and azide). Thus, a one-pot preparation of 1,4,5-trisubstituted 5-(2-alkoxy-1,2-dioxoethyl)-1,2,3-triazole was achieved by simply stirring the mixture of 1-copper(I) alkyne, azide, and alkoxalyl chloride at room temperature for 4 h.

CuCl-catalyzed aerobic oxidation of allylic and propargylic alcohols to aldehydes or ketones with 1:1 combination of phenanthroline and bipyridine as the ligands

We developed a modified protocol for the oxidation of 2,3-allenyl alcohols using CuCl with 1:1 combination of phenanthroline and bipyridine as the catalyst. To further investigate the applicability of this system, other types of alcohols such as allylic and propargylic alcohols have been tested: we found that both allylic and propargylic alcohols may be oxidized to the corresponding aldehydes or ketones using molecular oxygen in air as the oxidant with moderate to excellent yields. Copyright

PROCESS FOR PRODUCING ALDEHYDES OR KETONES BY OXIDIZING ALCOHOLS WITH OXYGEN

Provided is a process for producing aldehydes or ketones by oxidizing alcohols with oxygen, which comprises oxidizing alcohols to aldehydes or ketones in an organic solvent at room temperature with oxygen or air as an oxidant, wherein ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and an inorganic chloride are used as catalysts, the reaction time is 1-24 hours, and the molar ratio of said alcohols, 2,2,6,6-tetramethylpiperidine N-oxyl and the inorganic chloride is 100:1?10:1?10:1?10. The present process has the advantages of high yield, mild reaction conditions, simple operation, convenient separation and purification, recoverable solvents, substrates used therefor being various and no pollution, and therefore it is adaptable to industrialization.

Iron-catalyzed synthesis of β-chlorovinyl and α,β-alkynyl ketones from terminal and silylated alkynes with acid chlorides

A simple efficient method for the iron(III)-catalyzed synthesis of substituted β-chlorovinyl ketones and α,β-alkynyl ketones from terminal and silyl-substituted alkynes with acid chlorides, respectively, is described. This method features easily available

Development of a general and practical iron nitrate/TEMPO-catalyzed aerobic oxidation of alcohols to aldehydes/ketones: Catalysis with table salt

Oxidation of alcohols is a fundamental transformation related to our daily life. Traditional approaches with at least one stoichiometric amount of oxidants are expensive and cause serious environmental burdens. There are many reports on the aerobic oxidation of simple alcohols such as alkyl or phenyl carbinols and allylic alcohols, which used oxygen or air as the environmentally benign oxidant forming water as the only by-product. However, no such protocol has been reported for allenols and propargylic alcohols. Thus, it still highly desirable to develop efficient room temperature oxidations of alcohols with a wide scope including allenols and propargylic alcohols. In this paper, an efficient and clean aerobic oxidation of so far the widest spectrum of alcohols using 1 atm of oxygen or air, producing aldehydes/ketones at room temperature in fairly high isolated yields mostly within a couple of hours is described. It is interesting to observe that the reaction has been efficiently expedited by a catalytic amount of sodium chloride in easily recoverable 1,2-dichloroethane. A mechanism involving NO and NO2 has been proposed based on the results of the control experiments and GC-MS studies of the in-situ formed gas phase of the reaction mixture.