81939-73-3

Basic information

• Product Name: (S)-4-PENTYN-2-OL
• Synonyms: (S)-4-PENTYN-2-OL
• CAS NO: 81939-73-3
• Molecular Formula: C₅H₈O
• Molecular Weight: 84.11642
• Mol File: 81939-73-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-4-PENTYN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-PENTYN-2-OL(81939-73-3)
• EPA Substance Registry System: (S)-4-PENTYN-2-OL(81939-73-3)

Safety Data

• Hazardous Substances Data: 81939-73-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-PENTYN-2-OL is used as a building block in organic synthesis for the production of pharmaceuticals. Its ability to form carbon-carbon bonds through alkyne chemistry makes it a valuable component in the development of new drugs and medications.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-4-PENTYN-2-OL serves as a key component in the synthesis of various agrochemicals, contributing to the development of effective pest control solutions and other agricultural products.
Used in Specialty Chemicals:
(S)-4-PENTYN-2-OL is also utilized in the manufacturing of specialty chemicals, where its unique properties are harnessed to create high-quality and specialized chemical products.
Used as a Solvent:
Due to its solubility in water, ethanol, and diethyl ether, (S)-4-PENTYN-2-OL is used as a solvent in various chemical processes, facilitating reactions and improving the efficiency of production.
Used in Perfumery and Flavorings:
(S)-4-PENTYN-2-OL is employed in the manufacturing of perfumes and flavorings, where its distinctive odor and solubility properties contribute to the creation of unique and appealing scents and tastes.
Used as a Reagent in Chemical Reactions:
(S)-4-PENTYN-2-OL acts as a reagent in a range of chemical reactions, particularly in the formation of carbon-carbon bonds through alkyne chemistry, which is crucial for the synthesis of complex organic molecules.
Safety Precautions:
It is important to handle (S)-4-PENTYN-2-OL with care, as it can be irritating to the eyes, skin, and respiratory system. Proper safety measures should be taken to minimize potential health risks during its use and manipulation.

Upstream product

• 174953-30-1 (S)-(+)-4-methyl-2,2-dioxo-1,3,2-dioxathiolane 
• 74-86-2 acetylene 
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• 1066-54-2 trimethylsilylacetylene 
• 103712-19-2 (S)-(+)-5-(trimethylsilyl)-4-pentyn-2-ol 
• 32464-98-5 (2S)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 70277-75-7 lithium acetylide 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 

Downstream Products

• 120555-31-9 Ro 24-0238 
• 111954-72-4 (R)-α-methyl-3-pyridinebutanamine 
• 10048-32-5 (S)-parasorbic acid 
• 231291-69-3 (S)-4-Benzyloxy-pentan-1-ol 
• 231291-48-8 ((S)-4-Chloro-1-methyl-butoxymethyl)-benzene 
• 153681-99-3 (S)-N-benzyl-N-(Z)-(1-methyl-4-trimethylsilylbut-3-enyl)amine 
• 693790-22-6 (3R,5S)-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-(4-methoxybenzyloxy)propyl]thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethylethoxycarbonylamino)hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester 
• 693790-20-4 (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester 
• 693790-44-2 (3R,5S)-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-hydroxypropyl]thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethylethoxycarbonylamino)hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester 
• 693790-42-0 (3R,5S)-3-amino-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-(4-methoxybenzyloxy)propyl]thiazol-4-yl}hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester 
• 207129-91-7 (S)-((pent-4-yn-2-yloxy)methyl)benzene 

Relevant articles and documents

Concise Synthesis of a Pateamine A Analogue with in Vivo Anticancer Activity Based on an Iron-Catalyzed Pyrone Ring Opening/Cross-Coupling

The marine macrolide pateamine A and its non-natural sibling DMDA-Pat A are potent translation inhibitors targeting the eukaryotic initiation factor 4A (eIF4A), an enzyme with RNA helicase activity. Although essential for every living cell, this protein target seems "drugable" since DMDA-Pat A has previously been shown to exhibit remarkable in vivo activity against two different melanoma mouse models. The novel entry into this promising compound presented herein is shorter and significantly more productive than the literature route. Key to success was the masking of the signature Z,E-configured dienoate subunit of DMDA-Pat A in the form of a 2-pyrone ring, which was best crafted by a gold-catalyzed cyclization. While the robustness of the heterocycle facilitated the entire assembly stage, the highly isomerization-prone seco-Z,E-dienoic acid could be unlocked in due time for macrolactonization by an unconventional iron-catalyzed ring opening/cross coupling. Moreover, the crystal structure analysis of an advanced intermediate gave first insights into the conformation of the macrodilactone framework of the pateamine family, which is thought to be critical for eliciting the desired biological response.

Catalysis-Based Total Syntheses of Pateamine A and DMDA-Pat A

The marine natural product pateamine A (1) and its somewhat simplified designer analogue DMDA-Pat A (2) (DMDA = desmethyl-desamino) are potently cytotoxic compounds; most notably, 2 had previously been found to exhibit a promising differential in vivo activity in xenograft melanoma models, even though the ubiquitous eukaryotic initiation factor 4A (eIF4A) constitutes its primary biological target. In addition, 1 had also been identified as a possible lead in the quest for medication against cachexia, an often lethal muscle wasting syndrome affecting many immunocompromised or cancer patients. The short supply of these macrodiolides, however, rendered a more detailed biological assessment difficult. Therefore, a new synthetic approach to 1 and 2 has been devised, which centers on an unorthodox strategy for the formation of the highly isomerization-prone but essential Z,E-configured dienoate substructure embedded into the macrocyclic core. This motif was encoded in the form of a 2-pyrone ring and unveiled only immediately before macrocyclization by an unconventional iron-catalyzed ring opening/cross-coupling reaction, in which the enol ester entity of the pyrone gains the role of a leaving group. Since the required precursor was readily available by gold catalysis, this strategy rendered the overall sequence short, robust, and scalable. A surprisingly easy protecting group management together with a much improved end game for the formation of the trienyl side chain via a modern Stille coupling protocol also helped to make the chosen route practical. Change of a single building block allowed the synthesis to be redirected from the natural lead compound 1 toward its almost equipotent analogue 2. Isolation and reactivity profiling of pyrone tricarbonyliron complexes provide mechanistic information as well as insights into the likely origins of the observed chemoselectivity.

Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones

Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.

Total synthesis of 7′,8′-dihydroaigialospirol

A highly convergent total synthesis of 7′,8′- dihydroaigialospirol is described. Key steps of the synthesis include a Nozaki-Hiyama-Kishi (NHK) coupling of an iodoalkyne with an advanced phthalide-aldehyde and a remarkable one-pot acid-mediated global deprotection/spiroacetalization.

Synthesis of (-)-sedinine by allene cyclization and iminium Ion chemistry

A synthesis of the sedum alkaloid sedinine has been achieved employing silver(I)-catalyzed allenic hydroxylamine cyclization and ring-closing metathesis to form a bicyclic N,O-acetal. Ring opening of this acetal with a silyl enol ether under Lewis acidic conditions is exclusively trans selective, leading to the natural product after reduction. On the other hand, conversion of the bicyclic N,O-acetal to a semicyclic N,O-acetal results in no stereoselectivity during such a reaction. The contrasting results can be rationalized by consideration of the conformation of the iminium ions.

Macrocyclic kinase inhibitors

A compound having a structure according to formula I wherein R1, R2, R3, R4, and R5 are as defined herein, are useful as kinase inhibitors.

Rapid access to trans-2,6-disubstituted piperidines: Expedient total syntheses of (-)-solenopsin A and (+)-epi-dihydropinidine

Expedient syntheses of (-)-solenopsin A and (+)-epi-dihydropinidine are reported, the key step in both being the one-pot multicomponent aza-silyl-Prins condensation reaction to yield a trans dihydropyridine. Georg Thieme Verlag Stuttgart.

Zinc-acetic acid reductive cyclisation in a two-step synthesis of the S1-N10 nine-membered lactone core of ent-griseoviridin

The synthesis of the S1-N10 nine-membered lactone core 28 of enf-griseoviridin is reported. Starting from cystine derivative 25, encompassing a terminal ynoate, treatment under Zn/AcOH conditions led to the formation of lactone 28 in 12% yield. Therefore, the lactone moiety of enf-griseoviridin is obtained in 10.7% overall yield for two steps. An access to the corresponding 5-epi-griseoviridin lactone 29 is also described.

The effect of catechin derivatives on the enantioselectivity of lipase-catalyzed hydrolyses of alkynol benzoate esters

Polyphenols, such as (+)-catechin and pyrogallol could be used to enhance stereochemical control in the lipase-catalyzed hydrolysis of alkynol benzoate esters, leading to increased enantioselectivities in the kinetic resolution of alkynols with lipase Amano AH.

Approach toward the total synthesis of griseoviridin: Formation of thioethynyl and thiovinyl ether-containing nine-membered lactones through a thioalkynylation-macrolactonization-hydrostannylation sequence

Synthesis of the lactone core 17 of 8-epi-griseoviridin is reported. Thioethynyl derivative 11 was easily prepared via an anionic coupling reaction between acetylenic compound 9 and sulfone 10. After desilylation of 11, saponification of the resulting hydroxy ester 12 followed by a Mitsunobu macrolactonization furnished the unusual triple-bond-containing nine-membered lactone 13 in 50% yield for the last two steps (39% after recrystallization). Stannylation under Magriotis conditions led to the pure regio- and stereocontrolled vinyltin 14 (80% yield). After a Sn/I exchange, palladium-catalyzed carbonylation delivered either the ester lactone 16 in 67% yield or the propargyl amide 17 in 65% yield. Synthesis of propargyl amide 17 of the lactone core of 8-epi-griseoviridin was achieved in 11.9% overall yield from commercial L-cystin dimethyl ester (nine steps).