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
• Article Data: 18

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

General Description

(S)-4-Pentyn-2-ol is a chemical compound with the molecular formula C5H8O. It is a colorless liquid with a sharp, acrid odor, and is soluble in water, ethanol, and diethyl ether. (S)-4-Pentyn-2-ol is primarily used as a building block in organic synthesis, particularly in the production of pharmaceuticals, agrochemicals, and specialty chemicals. It is also used as a solvent and in the manufacturing of perfumes and flavorings. Additionally, it can act as a reagent in various chemical reactions, including the formation of carbon-carbon bonds through alkyne chemistry. However, it is important to handle this chemical with caution, as it can be irritating to the eyes, skin, and respiratory system.

Upstream product

• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 16088-62-3 (S)-Propylene oxide 
• 70277-75-7 lithium acetylide 
• 32464-98-5 (2S)-2-hydroxypropyl 4-methylbenzenesulfonate 
• 74-86-2 acetylene 
• 103712-19-2 (S)-(+)-5-(trimethylsilyl)-4-pentyn-2-ol 
• 1066-54-2 trimethylsilylacetylene 
• 174953-30-1 (S)-(+)-4-methyl-2,2-dioxo-1,3,2-dioxathiolane 

Downstream Products

• 207129-91-7 (S)-((pent-4-yn-2-yloxy)methyl)benzene 
• 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 

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.

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.

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.