Name: highly stereoselective synthesis of 1,6-ketoesters mediated by ionic liquids: a three-component reaction enabling rapid access to a new class of low molecular weight gelators
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Metil 6-okso-3,4,6-triphenylhexanoate 1. Gram ölçekli sentezi <ol><li> 10 mBar, 1 saat süre ile 40 ° C&#39;de bir döner buharlaştırıcı üzerinde bir yuvarlak tabanlı şişe içinde kuru 1-etil-3-metil imidazolyum asetat (EMIMAc). </li><li> Kuru EMIMAc 2.1 g ve 1,3-difenil-2-propen-1-on Manyetik bir karıştırıcı ile donatılmış 100 ml&#39;lik bir tabanı yuvarlak bir şişeye, 1.0 g ekleyin. </li><li> Metanol 2,019 ml ve şişeye sinamaldehid 2.3 g ekleyin. </li><li> Oda sıcaklığında (22 ° C) &#39;...

<ol>
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Ketoester 3 X-ışını analizi ile ve Bode ve işçiler 30 tarafından önerilen mekanik soruşturma belirlenen anti--konfigürasyonunda dayanarak aşağıdaki reaksiyon yolu (Şekil 5) önerilmektedir. IL protonasyonunun giderilmesi ve NHC türler oluşturan; NHC Breslow ara-ürün I. Breslow ara ürün oluşturmak üzere, doymamış aldehid ile reaksiyona girer ve kalkon dieni II oluşturulması için bir çapraz benzoin reaksiyona girmesi. Orta Düzey II anti-Odaklı ste...

<img alt="TOK 1" src="/files/ftp_upload/53213/53213TOC.jpg" /> (Yukarıda) 1,6-ketoesterlerden üç bileşenli sentezi: düşük molekül ağırlıklı gelators yeni bir sınıf. İyonik sıvılar (İS), yüksek stabilite, düşük bir uçuculuğa olmayan alev alma sahiptir ve bu yüzden dönüştürme için güvenli reaksiyon ortamı ve ideal çözücüler olarak dikkat hale getirmiştir. 1-3 Dialkil imidazolyumlar iyonik sıvılar belli bir tür olduğu, bir baz varlığında, , organobileşik alanında bir N-heterosiklik karben (NHC). 4 işlemek için deprotone edilebilir karbenlerin, farklı reaksiyon yolları altında faaliyet jenerik reaksiyonlar geniş bir yelpazede yaygın kullanım bulmuştur. 5-11 Buna rağmen, IL&#39;lerin ve CC bağ formin arasındaki bağlantıg NHC-kataliz nispeten keşfedilmemiş olduğunu. Bununla birlikte, IL&#39;lerin türetilen karbenlerin örneğin benzoin kondensasyon ve Stetter tepki olarak oluşturma reaksiyonlarında CC bağ katalize etmek için rapor edilmiştir. Örneğin, 12-22, Davis ve ark., N-alkil thiazoliums türetilen IL&#39;ler içinde ihtiva eden ön katalizörler olarak hizmet göstermiştir Benzaldehitten benzoin oluşumu. 12 Daha yakın zamanlarda, Chen ve arkadaşları, IL dayanan bir imidazolyum kullanarak bu kavramı genişletilmiş, 1-etil-3-metil imidazolyum asetat (EMIMAc) &#39;5,5 oluşturmak için 5-hidroksimetilfurfural (HMF) üzerine benzoin yoğunlaşma gerçekleştirmek için -di IL&#39;ler piyasada mevcuttur ve karbenlerin üreten ucuz bir yol sunar göz önüne alındığında (hidroksimetil) furoin (DHMF). 23, biz reaksiyonlar IL&#39;lerin diğer tip yerine ne olabilir soruşturma ilgilenmişlerdir. Bu amaçla, dialkil imidazolyumlar verimli formal konjügat Additi olarak ihtiva eden ön katalizörler olarak kullanılabileceğini buldukDoymamış aldehitlerin ilgili 1,6-ketoesterleri veren chalcone (Şekil 1). En verimli IL EMIMAc, sinamaldehid ve Kalkon arasında yüksek stereo reaksiyonu destekler. Reaksiyon, bir anti -diastereomeri yüksek tercihle oluşur ve 1,6-Ketoester 92 kadar% verimlerde izole edilebilir. 24,25,26 <img alt="figür 1" src="/files/ftp_upload/53213/53213fig1.jpg" /> Şekil 1: Üç bileşenli, Kalkon için sinamaldehid stereoselektif ek, IL-aracılı.

<table>
	<tbody>
		<tr>
			<td>1-ethyl-3-methyl imidazolium acetate</td>
			<td>Aldrich</td>
			<td>51053-100G-F</td>
			<td>Produced by BASF &#8805;90%, dried on a rotary evaporated before use (10 mBar, 40 &#176;C, 1h) 
			CAS NUMBER: 143314-17-4</td>
		</tr>
		<tr>
			<td>1,3-diphenyl-2-propen-1-one</td>
			<td>Aldrich</td>
			<td>11970-100G</td>
			<td>98.0% 
			CAS NUMBER: 94-41-7</td>
		</tr>
		<tr>
			<td>trans-cinnamaldehyde&#160;</td>
			<td>Aldrich</td>
			<td>C80687-25G</td>
			<td>99%, stored under nitrogen prior to use 
			CAS NUMBER: 14371-10-9</td>
		</tr>
		<tr>
			<td>1,8-Diazobicyclo[5.4.0]undec-7-ene</td>
			<td>Aldrich</td>
			<td>139009-25G</td>
			<td>98% 
			CAS NUMBER: 6674-22-2</td>
		</tr>
		<tr>
			<td>Methanol</td>
			<td>Sigma-Aldrich</td>
			<td>32213N-2.5L</td>
			<td>puriss. P.a., ACS reagent, reag. ISO, reag. Ph. Eur. &#8805;99.8% (GC) 
			CAS NUMBER: 67-56-1</td>
		</tr>
		<tr>
			<td>Dichloromethane</td>
			<td>Fischer Chemical</td>
			<td>D/1852/17X</td>
			<td>Analytic reagent grade, stabilized with amylene 
			CAS NUMBER:9/2/1975</td>
		</tr>
		<tr>
			<td>n-Heptane</td>
			<td>Fischer Chemical</td>
			<td>H/0160/17X</td>
			<td>Analytic reagent grade 
			CAS NUMBER: 142-82-5</td>
		</tr>
	</tbody>
</table>

highly stereoselective synthesis of 1,6-ketoesters mediated by ionic liquids: a three-component reaction enabling rapid access to a new class of low molecular weight gelators

In organic chemistry ionic liquids (ILs) have emerged as safe and recyclable reaction solvents. In the presence of a base ILs can be deprotonated to form catalytically active N-Heterocyclic Carbenes (NHCs). Here we have used ILs as precatalysts in the addition of &#945;,&#946;-unsaturated aldehydes to chalcones to form 1,6-ketoesters, incorporating an anti-diphenyl moiety in a highly stereoselective fashion. The reaction has a broad substrate scope and several functional groups and heteroaromatics can be integrated into the ketoester backbone in generally good yields with maintained stereoselectivity. The reaction protocol is robust and scalable. The starting materials are inexpensive and the products can be obtained after simple filtration, avoiding solvent-demanding chromatography. Furthermore, the IL can be recycled up to 5 times without any loss of reactivity. Moreover, the 1,6-ketoester end product is a potent gelator in several hydrocarbon based solvents. The method enables rapid access to and evaluation of a new class of low molecular weight gelators (LMWGs) from recyclable and inexpensive starting materials.

Yukarıda örneklendiği gibi, EMIMAc chalcone için α, β-doymamış aldehit resmi eşleniği ilave olarak bir precatalyst olarak görev yaparlar. Örneğin 1-etil-3-metil-imidazolyum klorür (EMIMCl) ve 1-butil-3-metil-imidazolyum klorür (BMIMCl) gibi başka ticari olarak temin edilebilen imidazolyum göre IL&#39;ler de incelenmiştir, ancak, asetat anyonu olabilir belirten düşük verimlerle devam bu reaksiyonların reaktivite (Tablo 1, giriş 1-3) için önemli. 27,28 *</sup...

Watch this Scientific Journal Video about Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Ionic liquids (ILs) mediate fast, simple and cheap access to 1,6-ketoesters in high diastereoselectivities and good yields. The reaction protocol is robust and the 1,6-ketoesters can be obtained in gram scale after a simple filtration protocol. Moreover, the 1,6-ketoesters are potent gelators in hydrocarbon solvents.

İyonik Sıvılar ARACILI 1,6-Ketoester son derece Stereoseçici Sentezi: Düşük Molekül Ağırlıklı Gelators Yeni Bir Sınıf Rapid Erişim etkinleştirilmesi A Üç bileşenli Tepki

In organic chemistry ionic liquids (ILs) have emerged as safe and recyclable reaction solvents. In the presence of a base ILs can be deprotonated to form ...

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Hazırlanması ve Samaryum Diiodide Kullanımı (SMI<sub&gt; 2</sub&gt;) In Organic Synthesis: Samaryum Barbier Reaksiyonu HMPA ve Ni (II) tuzlarının Mekanistik Rolü

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Due to their abundance in natural clay and potential applications in advanced materials, discotic nanoparticles are of interest to scientists and ...

Synthesis of Programmable Main-chain Liquid-crystalline Elastomers Using a Two-stage Thiol-acrylate Reaction

Bir iki-aşamalı Tiol akrilat reaksiyonu kullanılarak programlanabilir ana zincirli Sıvı kristal Elastomerler sentezi

This study presents a novel two-stage thiol-acrylate Michael addition-photopolymerization (TAMAP) reaction to prepare main-chain liquid-crystalline ...

Synthesis of Cd-free InP/ZnS Quantum Dots Suitable for Biomedical Applications

Biyomedikal Uygulamalar için uygundur InP / ZnS Kuantum Noktaları Cd-serbest sentezi

Fluorescent nanocrystals, specifically quantum dots, have been a useful tool for many biomedical applications. For successful use in biological systems, ...

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

Sentezi İçin Protokol<em&gt; Ortho</em&gt; -trifluoromethoxylated Anilin türevleri

Molecules bearing trifluoromethoxy (OCF3) group often show desired pharmacological and biological properties. However, facile synthesis of ...

Facile Synthesis of Worm-like Micelles by Visible Light Mediated Dispersion Polymerization Using Photoredox Catalyst

Photoredox Katalizörü kullanarak görünür ışık aracılığı ile dispersiyon polimerleştirilmesi ile solucan gibi miseller Facile sentezi

Presented herein is a protocol for the facile synthesis of worm-like micelles by visible light mediated dispersion polymerization. This approach begins ...

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Malzemeler molekülleri üzerinden: yeni iyonik sıvı kristaller halojen yoluyla mühendislik

Herein, we demonstrate that a bottom-up approach, based on halogen bonding (XB), can be successfully applied for the design of a new type of ionic liquid ...

Fabrication and Testing of Catalytic Aerogels Prepared Via Rapid Supercritical Extraction

İmalat ve katalitik Aerogels hızlı süperkritik ayıklama hazırlanan test

Protocols for preparing and testing catalytic aerogels by incorporating metal species into silica and alumina aerogel platforms are presented. Three ...

Rapid Nanoprobe Signal Enhancement by In Situ Gold Nanoparticle Synthesis

Rapid Nanoprobe Signal Enhancement by In Situ Gold Nanoparticle Synthesis

Hızlı Nanoprobe sinyal geliştirme içinde in Situ altın nanoparçacık sentezi tarafından

The use of nanoprobes such as gold, silver, silica or iron-oxide nanoparticles as detection reagents in bioanalytical assays can enable high sensitivity ...