1070-40-2

Usage

Uses

Used in Organic Synthesis:
5-Decyne-4,7-diol is used as a building block in organic synthesis for its ability to form complex structures through its unique chemical properties, contributing to the development of novel organic compounds.
Used in Materials Science:
In the field of materials science, 5-Decyne-4,7-diol is utilized for its potential to create innovative materials, leveraging its capacity to form intricate molecular arrangements.
Used in Pharmaceutical Production:
5-Decyne-4,7-diol is employed as a precursor in the synthesis of various pharmaceuticals, playing a crucial role in the development of new drugs and medicinal compounds.
Used in the Synthesis of Organic Compounds:
As a precursor, 5-Decyne-4,7-diol is used in the synthesis of a range of organic compounds, highlighting its importance in the chemical industry for creating diverse chemical entities.
It is important to handle 5-Decyne-4,7-diol with proper safety measures due to its potential hazards if not managed correctly.

InChI:InChI=1/C10H18O2/c1-3-5-9(11)7-8-10(12)6-4-2/h9-12H,3-6H2,1-2H3

Upstream product

• 4301-15-9 ethynyldimagnesium dibromide 
• 123-72-8 butyraldehyde 
• 1117-94-8 copper(I) acetylide 
• 74-86-2 acetylene 
• 1942-46-7 5-decyne 
• 1817-52-3 dec-5-yn-4-ol 
• 105-31-7 1-hexyn-3-ol 
• 5111-44-4 2-methyloct-3-yne-2,5-diol 
• 693-02-7 hex-1-yne 

Downstream Products

• 4469-89-0 4,7-decanediol 
• 97-61-0 2-Methylpentanoic acid 

Relevant academic research and scientific papers

Cycloaddition Reaction of Vinylphenylfurans and Dimethyl Acetylenedicarboxylate to [8 + 2] Isomers via Tandem [4 + 2]/Diradical Alkene-Alkene Coupling/[1,3]-H Shift Reactions: Experimental Exploration and DFT Understanding of Reaction Mechanisms

An experimental test of designed [8 + 2] reaction of vinylphenylfuran and dimethyl acetylenedicarboxylate (DMAD) has been carried out, showing that the reaction gave unexpected addition products under different conditions. When the reaction was conducted under thermal conditions in toluene, expoxyphenanthrene, which was named as a [8 + 2] isomer, was generated. The scope of this reaction has been investigated in the present study. In addition, experiments and DFT calculations have been conducted to investigate how the reaction between vinylphenylfuran and DMAD took place. Surprisingly, the reaction did not involve the expected [8 + 2] intermediate, o-quinodimethane. Instead, the reaction starts from intermolecular Diels-Alder reactions between DMAD and the furan moiety of vinylphenylfuran, followed by unexpected intramolecular alkene-alkene coupling. This step generates a diradical species, which then undergoes [1,3]-H shift to give the experimentally observed expoxyphenanthrene. DFT calculations revealed that, the [8 + 2] cycloadduct cannot be obtained because the [1,5]-H shift process from the [1,5]-vinyl shift intermediate is disfavored kinetically compared to the [1,3]-H shift to the [8 + 2] isomer.

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.

Highly Stereoselective approach to Alk-2-yne-1,4-diols by oxazaborolidine-mediated reduction of Alk-2-yne-1,4-diones

We performed the borane-mediated reduction of a series of symmetrical alk-2-yne-1,4-diones (5) in the presence of the oxazaborolidine (R)-6 to afford (R,R)-alk-2-yne-1,4-diols ((R,R)-1) in good yields and high stereoselectivities (up to 99.9% ee). In some cases, the stereochemical purity of 1 was improved by a two-step process: (i) temporary transformation of 1 into its vic-dibromo derivatives 9, which allowed us to remove the minor meso isomer by chromatography, and (ii) regeneration of the enantioenriched diols 1 with SmI2. Reduction of the hexacarbonyldicobalt complexes 8 derived from 5 was also successful.