99902-35-9

Usage

Uses

Used in Organic Synthesis:
(R)-3-hydroxy-5-phenyl-1-pentyne is used as a building block in organic synthesis for the creation of more complex molecules. Its unique structure, including the alkyne and phenyl groups, allows for a variety of chemical reactions, making it a versatile component in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
(R)-3-hydroxy-5-phenyl-1-pentyne is used as an intermediate in the development of pharmaceutical compounds. Its chiral nature and functional groups can be exploited to create enantiomerically pure drugs, which are essential for ensuring the desired therapeutic effects and minimizing side effects.
Used in Chemical Industry:
(R)-3-hydroxy-5-phenyl-1-pentyne is utilized as a specialty chemical in various applications within the chemical industry. Its properties may be harnessed for the production of materials with specific characteristics, such as coatings, adhesives, or polymers with tailored properties.
Used in Research:
(R)-3-hydroxy-5-phenyl-1-pentyne is used as a subject of research to explore the properties and reactivity of alkynes and chiral compounds. Understanding its behavior in chemical reactions can lead to the discovery of new synthetic routes and applications in various fields.

Upstream product

• 104-53-0 3-phenyl-propionaldehyde 
• 1066-26-8 sodium acetylide 
• 74-86-2 acetylene 
• 65032-27-1 ethynylmagnesium chloride 
• 140149-77-5 5-phenyl-1-trimethylsilylpent-1-yn-3-ol 
• 4301-14-8 acetylenemagnesium bromide 
• 122-97-4 3-Phenyl-1-propanol 
• 1027627-26-4 C₂₀H₃₄OSi₂ 
• 110211-31-9 Acetic acid 1-phenethyl-3-trimethylsilanyl-prop-2-ynyl ester 
• 67-56-1 methanol 
• 100330-45-8 (+/-)-1-(2-Phenylethyl)-3-propynyl acetate 
• 591-50-4 iodobenzene 
• 99902-30-4 (3R,5R)-3-methyl-5-(2'-phenylethyl)-4-oxahept-6-insaeure 
• 118584-91-1 5-phenylpent-1-yn-3-one 

Downstream Products

• 67647-96-5 nona-3,4-dien-1-ylbenzene 
• 67647-98-7 (6,6-dimethylhepta-3,4-dienyl)benzene 
• 84733-04-0 (3S)-3-(tert-butyldimethylsiloxy)-5-phenyl-1-pentyne 
• 130325-03-0 (Z)-(S)-1-Iodo-5-phenyl-pent-1-en-3-ol 
• 135450-08-7 ethyl (1-ethynyl-3-phenylpropoxy)acetate 
• 100330-45-8 (+/-)-1-(2-Phenylethyl)-3-propynyl acetate 
• 453574-71-5 3,3-dimethyl-5-phenylethyl-4-oxa-3-sila-1-hepten-6-yne 
• 710313-46-5 (E)-6-methyl-1-phenyloct-6-en-4-yn-3-ol 
• 152710-05-9 5-phenyl-1-pentyn-3-yl methanesulfonate 
• 880085-52-9 methyl 5-phenylpent-1-yn-3-yl carbonate 
• 40339-21-7 penta-3,4-dienyl-benzene 
• 913977-01-2 C₁₅H₁₈O 

Relevant academic research and scientific papers

Sc(OTf)3-catalyzed [3 + 2]-cycloaddition of nitrones with ynones

An efficient approach to access functionalized (2,3-dihydroisoxazol-4-yl) ketones has been developed by reacting nitrones 4 with ynones 7 or terminal ynones 10 in a one-pot fashion. The reaction went through a formal Sc(OTf)3-catalyzed [3 + 2]-cycloaddition process to generate a number of functionalized (2,3-dihydroisoxazol-4-yl) ketones 11aa-11aw, 11ba-11la and 12aa-12ae in moderate to good yields. This journal is

Enantioselective [3 + 2] annulation of 4-isothiocyanato pyrazolones and alkynyl ketones under organocatalysis

An asymmetric [3 + 2] annulation reaction of 4-isothiocyanato pyrazolones with alkynyl ketones in the presence of an organic catalyst derived from a cinchona alkaloid under mild conditions is realized. This protocol provides unprecedented expeditious access to a wide range of optically active spiro[pyrroline-pyrazolones] with various electronic properties in high yields with good to excellent enantioselectivities.

Synthesis of Difluorinated Dihydrobenzo[de]chromenes via Rh(III)-Catalysed C-H Couplings of 1-Naphthols with Gem-Difluoromethylene Alkynes

The Rh(III)-catalysed C?H couplings of 1-naphthols with gem-difluoromethylene alkynes have been realized for the direct construction of difluorinated dihydrobenzo[de]chromenes with broad substrate/functional group compatibility and good regio-/chemoselect

A Convergent, Stereoselective Route to Trisubstituted Alkenyl Boronates

A modular, stereoselective route to trisubstituted (Z)-alkenyl (MIDA)boronates is described, consisting of the radical addition-fragmentation of dithiocarbonates to 2-(MIDA)boronyl-3-(2′-fluoro-pyridyl-6′-oxy)-alkenes. The bulky (MIDA)boronate ensures a highly stereoselective fragmentation that is enhanced by the poor stabilization of the radical adjacent to the tetravalent boron atom. The vinyl boronate precursors are prepared from propargyl alcohols by copper-catalyzed regioselective protoboration of their fluoropyridoxy derivatives, with the fluoropyridine acting as an internal directing group.

Transition-Metal-Free Synthesis of Electron Rich 1,3-Dienes via Base Promoted Isomerization of Propargylic Ethers

Herein, a novel and scalable synthesis of electron rich 1,3-dienes based on KOtBu mediated isomerization of propargylic ether derivatives was developed. This new process features easy handling reaction conditions, transition-metal-free isomerization, high isolated yields, and most of all, it could be used for modification of natural products at late stage functionalizations.

Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (?)-centrolobine.

Drastic fluorine effect: Complete reversal of the selectivity in the Au-catalyzed hydroalkoxylation reaction of fluorinated haloalkynes

The gold-catalyzed hydration reaction of haloalkynes is highly regioselective producing 2-halomethylketones as the sole products. Herein, we document a drastic fluorine effect where the reaction of 1-halo-3,3-difluoroalkynes as substrates leads to a complete reversal of selectivity and produces 3,3-difluoroesters as the unique products.

Rhodium-Catalyzed Parallel Kinetic Resolution of Racemic Internal Allenes Towards Enantiopure Allylic 1,3-Diketones

A rare case of a parallel kinetic resolution of racemic 1,3-disubstituted allenes by means of a rhodium-catalyzed addition to 1,3-diketones furnishing enantiopure allylic 1,3-diketones is described. Mechanistic experiments demonstrate that the different allene enantiomers react in parallel to either the diastereomeric E- or Z-allylic 1,3-diketones with the same absolute configuration of the newly formed stereogenic center. A broad substrate scope demonstrates the synthetic utility of this new method.

Palladium- and Rhodium-Catalyzed Dynamic Kinetic Resolution of Racemic Internal Allenes Towards Chiral Pyrazoles

A complementing Pd- and Rh-catalyzed dynamic kinetic resolution (DKR) of racemic allenes leading to N-allylated pyrazoles is described. Such compounds are of enormous interest in medicinal chemistry as certified drugs and potential drug candidates. The new methods feature high chemo-, regio- and enantioselectivities aside from displaying a broad substrate scope and functional group compatibility. A mechanistic rational accounting for allene racemization and trans-alkene selectivity is discussed.