55563-79-6

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-4-PENTEN-2-OL is used as a key intermediate in the synthesis of various pharmaceutical compounds, such as goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid. These compounds have been found to possess a range of biological activities, including anti-inflammatory, analgesic, and anti-cancer properties. The application of (S)-(+)-4-PENTEN-2-OL in this industry is driven by its ability to facilitate the production of these therapeutically relevant molecules.
Used in Chemical Synthesis:
(S)-(+)-4-PENTEN-2-OL is used as a versatile building block in the synthesis of various organic compounds, such as 2-pentanone. Its unique chemical structure allows it to participate in a wide range of reactions, including allylboration, esterification, and ring-closing metathesis. This makes it a valuable asset in the development of new chemical entities and the improvement of existing synthetic routes.

InChI:InChI=1/C5H10O/c1-3-4-5(2)6/h3,5-6H,1,4H2,2H3/t5-/m0/s1

Upstream product

• 64584-91-4 phthalic acid mono-(1-methyl-but-3-enyl) ester 
• 7785-70-8 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene 
• 75-07-0 acetaldehyde 
• 1730-25-2 allylmagnesium bromide 
• 111957-98-3 Pent-4-en-2-ol 
• 760181-72-4 (R)-2-(4-methoxybenzyloxy)pent-4-en-1-ol 
• 847049-72-3 1-methoxy-4-{[(2S)-pent-4-en-2-yloxy]methyl}benzene 
• 142561-89-5 (R)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 
• 874660-40-9 (R)-2-(4-Methoxy-benzyloxy)-pent-4-enal 
• 108-05-4 vinyl acetate 
• 1384108-64-8 C₅H₉O₄S^(1-)*Na⁽¹⁺⁾ 
• 1384108-43-3 C₅H₉O₄S^(1-)*Na⁽¹⁺⁾ 
• 1826-67-1 vinyl magnesium bromide 
• 75-56-9 methyloxirane 

Downstream Products

• 717124-38-4 (S)-2-(4-methoxyphenoxy)-4-pentene 
• 12772-57-5 (9Z,11E)-(4R,6R,8R)-16-Chloro-17,19-dihydroxy-4-methyl-3,7-dioxa-tricyclo[13.4.0.0^6,8]nonadeca-1⁽¹⁵⁾,9,11,16,18-pentaene-2,13-dione 
• 867367-94-0 2,4-Dihydroxy-6-methyl-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester 
• 378750-02-8 (3R,4R,6S)-6-(tert-butyldiphenylsilyl)-3,4-(oxiranyl)hept-1-ene 
• 867367-83-7 2,4-Bis-methoxymethoxy-6-methyl-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester 
• 754201-26-8 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3S)-3-vinyl-oxiranyl)-ethyl ester 
• 867367-85-9 2,4-Bis-methoxymethoxy-6-((E)-2-oxo-hexa-3,5-dienyl)-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester 
• 1147106-37-3 (2Z,4E)-((S)-pent-4-en-2-yl) 3-ethyl-4-(4-methylbenzoyl)hexa-2,4-dienoate 
• 1147106-49-7 (2Z,4E)-((S)-pent-4-en-2-yl) 4-(4-bromobenzoyl)-3-methylnona-2,4,8-trienoate 
• 1147106-54-4 (S,2Z,4E)-((S)-pent-4-en-2-yl) 4-(4-bromobenzoyl)-3-ethyl-7,11-dimethyldodeca-2,4,10-trienoate 

Relevant academic research and scientific papers

Total synthesis of (–)-cephalosporolide D

In this communication, a concise and efficient synthetic route for the synthesis of (–)-Cephalosporolide D in enantioselective way has been described. In this synthesis, Mitsunobu esterification and Ring Closing Metathesis (RCM) for macrocyclic ring formation have been applied as key steps.

Copper-Catalyzed Enantiotopic-Group-Selective Allylation of gem-Diborylalkanes

We report a copper-catalyzed enatiotopic-group-selective allylation of gem-diborylalkanes with allyl bromides. The combination of copper(I) bromide and H8-BINOL derived phosphoramidite ligand proved to be the most effective catalytic system to provide various enantioenriched homoallylic boronate esters, containing a boron-substituted stereogenic center that is solely derived from gem-diborylalkanes, in good yields with high enantiomeric ratios under mild conditions. Experimental and theoretical studies have been conducted to elucidate the reaction mechanism, revealing how the enatiotopic-group-selective transmetalation of gem-diborylalkanes with chiral copper complex occurs to generate chiral α-borylalkyl-copper species for the first time. Additional synthetic applications to the synthesis of various chiral building blocks are also included.

A Short Synthesis of (+)-Brefeldin C through Enantioselective Radical Hydroalkynylation

A very concise total synthesis of (+)-brefeldin C starting from 2-furanylcyclopentene is described. This approach is based on an unprecedented enantioselective radical hydroalkynylation process to introduce the two cyclopentane stereocenters in a single step. The use of a furan substituent allows a high trans diastereoselectivity to be achieved during the radical process and it contains the four carbon atoms C1–C4 of the natural product in an oxidation state closely related to the one of the target molecule. The eight-step synthesis requires six product purifications and it provides (+)-brefeldin C in 18 % overall yield.

Carbohydrate/DBU Cocatalyzed Alkene Diboration: Mechanistic Insight Provides Enhanced Catalytic Efficiency and Substrate Scope

A mechanistic investigation of the carbohydrate/DBU cocatalyzed enantioselective diboration of alkenes is presented. These studies provide an understanding of the origin of stereoselectivity and also reveal a strategy for enhancing reactivity and broadening the substrate scope.

Synthesis and Stereochemical Assignment of Arenolide

The convergent synthesis of candidate stereoisomers of the natural product arenolide was accomplished using recently developed catalytic boron-based reactions. Comparison of the spectral data for candidate structures with that reported for the authentic natural product revealed the likely stereostructure of the natural compound.

[1,3]thiazin-2-amine compounds as well as applications and pharmaceutical compositions thereof

The invention relates to [1,3]thiazin-2-amine compounds as well as applications and pharmaceutical compositions thereof, and belongs to the field of BACE (beta-site amyloid precursor protein cleavingenzyme) inhibitors. The [1,3]thiazid-2-amine compounds are compounds, pharmaceutically acceptable salts, stereoisomers, solvates, or prodrugs represented by a formula (I), and the formula (I) is shownin the description. The [1,3]thiazin-2-amine compounds provided by the invention have good inhibiting effects on BACE, and can be used for the preparation of medicines for treating neurodegenerativediseases such as alzheimer diseases.

Mechanistic Studies on a Cu-Catalyzed Asymmetric Allylic Alkylation with Cyclic Racemic Starting Materials

Mechanistic studies on Cu-catalyzed asymmetric additions of alkylzirconocene nucleophiles to racemic allylic halide electrophiles were conducted using a combination of isotopic labeling, NMR spectroscopy, kinetic modeling, structure-activity relationships, and new reaction development. Kinetic and dynamic NMR spectroscopic studies provided insight into the oligomeric Cu-ligand complexes, which evolve during the course of the reaction to become faster and more highly enantioselective. The Cu-counterions play a role in both selecting different pathways and in racemizing the starting material via formation of an allyl iodide intermediate. We quantify the rate of Cu-catalyzed allyl iodide isomerization and identify a series of conditions under which the formation and racemization of the allyl iodide occurs. We developed reaction conditions where racemic allylic phosphates are suitable substrates using new phosphoramidite ligand D. D also allows highly enantioselective addition to racemic seven-membered-ring allyl chlorides for the first time.1H and2H NMR spectroscopy experiments on reactions using allylic phosphates showed the importance of allyl chloride intermediates, which form either by the action of TMSCl or from an adventitious chloride source. Overall these studies support a mechanism where complex oligomeric catalysts both racemize the starting material and select one enantiomer for a highly enantioselective reaction. It is anticipated that this work will enable extension of copper-catalyzed asymmetric reactions and provide understanding on how to develop dynamic kinetic asymmetric transformations more broadly.

Nickel-Catalyzed Enantioselective Conjunctive Cross-Coupling of 9-BBN Borates

Catalytic enantioselective conjunctive cross-coupling between 9-BBN borate complexes and aryl electrophiles can be accomplished with Ni salts in the presence of a chiral diamine ligand. The reactions furnish chiral 9-BBN derivatives in an enantioselective fashion and these are converted to chiral alcohols and amines, or engaged in other stereospecific C?C bond forming reactions.

Asymmetric Synthesis of Borylalkanes via Copper-Catalyzed Enantioselective Hydroallylation

An efficient synthetic method for preparing enantioenriched secondary borylalkanes has been achieved through a copper-catalyzed regio- and enantioselective hydroallylation of alkenyl boronates and boramides employing hydrosilanes and allylic phosphates. In the presence of a copper catalyst with a chiral Walphos ligand, a range of alkenylboron compounds with an aryl, heteroaryl, or alkyl substituent produced secondary homoallylic alkylboron compounds in good yields and with high enantioselectivities up to 99% ee. The utility of the resulting alkylboronates was demonstrated in an efficient synthesis of (S)-massoialactone.

Synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin: A facile and stereoselective approach

A concise and facile synthesis of (3R,5S)-5-hydroxy-de-O-methyllasiodiplodin has been demonstrated in 12 steps starting from methylacetoacetate and (±)propylene oxide. The key reactions involved are Jacobsen's hydrolytic kinetic resolution, Sharpless asymmetric epoxidation, Mitsunobu, and ring closing metathesis reaction for the construction of macrolactone with two chiral substitutions on it.