927-57-1

Usage

InChI:InChI=1/C5H8O2/c1-5(7)3-2-4-6/h5-7H,4H2,1H3

Upstream product

• 75-07-0 acetaldehyde 
• 107-19-7 propargyl alcohol 
• 50-00-0 formaldehyd 
• 2028-63-9 but-3-yn-2-ol 
• 7732-18-5 water 
• 1117-94-8 copper(I) acetylide 
• 114419-86-2 4-methyl-4-(tetrahydro-2-pyranyloxy)-2-butyn-1-ol 
• 14092-30-9 5-<(Tetrahydro-2H-pyran-2-yl)oxy>-3-pentyn-2-ol 
• 925-90-6 ethylmagnesium bromide 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 626-95-9 1,4-Pentanediol 
• 192136-81-5 C₂₁H₂₂N₂O₈S₂ 
• 1079308-83-0 N,N'-bis(tert-butyloxycarbonyl)-N,N'-bis[(4-methylphenyl)sulfonyl]-1-methyl-2-butyn-1,4-diamine 
• 651044-37-0 (1-O-dibenzylphosphoryl)-1-hydroxy-4-oxo-pent-2-ene 
• 651044-36-9 (1-O-dibenzylphosphoryl)-1,4-dihydroxypent-2-ene 

Relevant academic research and scientific papers

Enzymatic kinetic resolution of internal propargylic diols. Part I: A new approach for the synthesis of (S)-pent-2-yn-1,4-diol, a natural product from Clitocybe catinus

Internal bis-substituted propargylic diols were subjected to enzymatic kinetic resolution promoted by CAL-B. Employing a two round sequence EKR, mono- and bis-acetoxy propargylic products were obtained in a high enantiomeric ratio (E > 200). The efficiently resolved chiral 8b was applied in a concise synthesis of (S)-1b, an optically active natural product produced by fungi Clitocybe catinus.

Method for synthesizing inducing component 4-oxo-trans-2-hexenal in sex pheromones of miridae

The invention discloses a method for synthesizing an inducing component 4-oxo-trans-2-hexenal in sex pheromones of miridae. The method comprises the following steps that (1) under the effect of base,propargyl alcohol and acetaldehyde have a substitution reaction to obtain 1-methyl-1,4-butynediol; (2) 1-methyl-1,4-butynediol obtained in step (1) has a reduction reaction under the effect of a reducing agent to obtain 1-methyl-1,4-butenediol; (3) 1-methyl-1,4-butenediol obtained in step (2) has an oxidation reaction under the effect of an oxidizing agent, and after the reaction is finished, 4-oxo-trans-2-hexenal is obtained through treatment. The synthesis method has a short route, the reaction yield of each step is high at the same time, the operation is simple, and the mass production is facilitated.

CeCl3-mediated addition of acetylenic bis-lithium salts to aldehydes and ketones: An efficient route to bis-substituted alkyne diols

An efficient, chemoselective protocol to access propargylic diols via a CeCl3-mediated addition reaction is reported. Propargylic alcohols were transformed into the corresponding acetylenic bis-lithium salt intermediates, which react with aldehydes and ketones in the presence of dry CeCl3 to furnish the corresponding bis-substituted alkyne diols. This protocol does not involve protection-deprotection or transmetallation steps, and allows the use of poorly reactive or highly enolizable substrates.

Iron-catalyzed sustainable synthesis of pyrrole

Efficient, sustainable, highly regiospecific substituted pyrroles were synthesized using a well-defined, air stable, molecular iron(0) complex. The developed methodology is broadly applicable and tolerates a variety of functional groups. C-2, C-3, and C-2 & C-4 substituted pyrroles were synthesized in good yield. Symmetrical bis-pyrroles were accessible for the first time using an iron catalyst. On the basis of the experimental observation, we propose that the reaction proceeds through a hydrogen autotransfer process followed by second oxidation/ intramolecular dehydrative condensation to provide the pyrrole.

Synthesis and in vitro evaluation of (R), (S) and (R/S)-2-hexyne-1,4-diol, a natural product produced by fungus Clitocybe catinus, and related analogs as potential anticancer agents

The search for natural products and related analogs as potential anticancer agents has seen a significant growth worldwide. Since small sized propargylic diols can be found in nature and chemically synthesized, their evaluation against cancer cells has been of great interest, being a topic of relevance to be investigated. For this purpose, a scalable approach aiming at the synthesis of several propargylic diols and their bioactivity against seven tumor cell lines were evaluated. Interestingly, when the compound 1a, a natural product produced by fungus Clitocybe catinus, was tested in its racemic mixture a more effective activity was observed if compared when enantiopure R-1a or S-1a were tested separately.

Some special features of hydroalumination-iodination of alkyne-1,4-diols

Hydroalumination-iodination of alkyne-1,4-diols of different structure showed that with increasing number of substituents at the C-OH group the amount of β-iodo-substituted products with respect to this group increased. In the case of symmetric secondary 1,4-diols the reaction results in a 1: 1 mixture of stereoisomeric iodoalkenediols, and in the case of phenyl substituents the reaction proceeds regio- and stereoselectively to give an alkenediol iodine atom in the β-position to phenyl group.

Ruthenium-catalyzed [2 + 2] cycloadditions between norbornene and propargylic alcohols or their derivatives

Diastereoselective ruthenium-catalyzed [2 + 2] cycloadditions of norbornene and propargylic alcohols or their derivatives were investigated. The cycloadditions were found to be highly stereoselective, giving exo cycloadducts in moderate to excellent yields with diastereoselectivities up to 92:8. When a chiral propargylic alcohol was used in the cycloaddition, up to 80% ee of the [2 + 2] cycloadducts was observed after oxidation of the alcohol.

Preparation, structure, and unique thermal [2 + 2], [4 + 2], and [3 + 2] cycloaddition reactions of 4-vinylideneoxazolidin-2-one

The terminal allene Cα=Cβ bonds of 4-vinylidene-2-oxazolidinone (2) readily undergo [2 + 2] cycloaddition with a wide variety of terminal alkynes, alkenes, and 1,3-dienes irrespective of their electronic nature under strictly thermal activation conditions (70-100°C) and provide 3-substituted (Z)-methylenecyclobutenes 6, 3-substituted methylenecyclobutanes 7 and 8, and 3-vinylmethylenecyclobutanes 9, respectively, in good to excellent yields. Alkenes react with 2 with complete retention of configuration. The [2 + 2] cycloaddition is concluded to proceed via a concerted [(π2s + π2s)allene + π2s] Hueckel transition state on the basis of experimental evidences and quantum mechanical methods. Some highly polarized enones and nitrile oxide, on the other hand, react with 2 selectively at the internal C4=Cα double bonds and give spiro compounds 10 and 11, respectively. The bent allene bonds (173-176°) and the unique reactivity associated with 2 are attributed to a low-lying LUMO (Cα=Cβ) that is substantiated by a through-space σ*(N-SO2)-π*(Cα= Cβ) orbital interaction.

ASSESSMENT OF BUTENE-1,4-DIOLS AS STARTING MATERIALS FOR THE PREPARATION OF ?-ALLYLTRICARBONYLIRON COMPLEXES

This work assesses the use of butene-1,4-diols as starting materials for the synthesis of ?-allyltricarbonyliron lactone complexes.It has been shown that substituents, and the use of Lewis acids, mainly ZnBr2, in reactions with Fe2(CO)9 in benzene under ultrasonic conditions or in THF, greatly influence the yield and the product distribution.