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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1. غرام النطاق توليف الميثيل 6 أوكسو-3،4،6-triphenylhexanoate <ol style=";text-align:right;direction:rtl"><li style=";text-align:right;direction:rtl"> الجاف 1-ايثيل-3-الميثيل خلات imidazolium (EMIMAc) في قاع القارورة المستديرة حول المبخر الدوار في 10 ميللي بار، 40 ° C لمدة 1 ساعة. </li><li style=";text-align:right;direction:rtl"> إضافة 2.1 غرام من EMIMAc الجا...

<ol>
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استنادا إلى -configuration المضادة التي يحددها التحليل بالأشعة السينية ketoester 3 وعلى التحقيق الآلية التي اقترحها بوده وزملاء العمل 30 واقترح مسار التفاعل التالي (الشكل 5). نزع بروتون من IL يولد نوعا NHC. وNHC يتفاعل مع ألدهيد غير مشبعة لتشكيل بريسلو سيطة أولا بر...

<img alt="TOC 1" src="/files/ftp_upload/53213/53213TOC.jpg" /> (فوق) تركيب ثلاثي مكون من 1،6-ketoesters: فئة جديدة من الاسعار المنخفضة gelators الوزن الجزيئي. السوائل الأيونية (ILS) لديها استقرار عالية، وتقلب أسعار منخفضة، وعدم قابليتها للاشتعال، وبالتالي جعلت اهتمام وسائل الإعلام رد فعل آمنة والمذيبات مثالية لإعادة التدوير. 1-3 imidazoliums الألكيل هي نوع معين من السوائل الأيونية أنه في وجود قاعدة ، يمكن deprotonated لإصدار-N الحلقية غير المتجانسة carbene (NHC). 4 في مجال organocatalysis، NHCs، التي تعمل تحت مسارات رد فعل متميزة، وقد وجدت استخدام على نطاق واسع في مجموعة واسعة من ردود الفعل العامة. 5-11 وعلى الرغم من ذلك، فإن العلاقة بين ILS وformin السندات CCز NHC الحفز غير مستكشفة نسبيا. ومع ذلك، فقد تم الإبلاغ عن NHCs المستمدة من ILS لتحفيز CC السندات تشكيل ردود الفعل مثل التكثيف الجاوي وردود الفعل ستتر. 12-22 فعلى سبيل المثال، أظهرت ديفيس وآخرون أن ILS المستمدة من thiazoliums N-ألكيل بمثابة precatalysts في تشكيل الجاوي من بنزيلديهايد 12 في الآونة الأخيرة، وتشن وزملاء العمل توسيع هذا المفهوم باستخدام imidazolium استنادا IL، 1 إيثيل-3-الميثيل imidazolium خلات (EMIMAc)، لأداء التكثيف الجاوي على 5 hydroxymethylfurfural (HMF) لتوليد 5،5 &#39;-di (hydroxymethyl) furoin (DHMF). 23 وبالنظر إلى أن وILS المتاحة تجاريا وتوفر وسيلة غير مكلفة لتوليد NHCs، ونحن مهتمون في التحقيق في ما أنواع أخرى من ردود الفعل ILS يمكن أن تؤدي. تحقيقا لهذه الغاية، وجدنا أن الألكيل imidazoliums يمكن أن تستخدم بكفاءة precatalysts في المترافقة additi الرسميعلى الألدهيدات غير المشبعة إلى الجالكونات (الشكل 1) إعطاء 1،6-ketoesters. وIL الأكثر كفاءة، EMIMAc، ويعزز رد فعل فراغي للغاية بين سينمالدهيد وكالكون. يحدث رد فعل مع تفضيل عالية لمكافحة -diastereomer و-ketoesters 1،6 يمكن عزل في عوائد تصل إلى 92٪. 24،25،26 <img alt="الشكل 1" src="/files/ftp_upload/53213/53213fig1.jpg" /> الشكل 1: IL بوساطة ثلاثة مكونات، بالإضافة فراغي من سينمالدهيد إلى كالكون.

<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.

<html> كما يتضح أعلاه، EMIMAc بمثابة precatalyst في إضافة المترافقة الرسمية للα، β-غير المشبعة ألدهيد إلى الجالكونات. وتم التحقيق أيضا الأخرى المتاحة تجاريا ILS استنادا imidazolium مثل كلوريد 1-ايثيل-3-methylimidazolium (EMIMCl) وكلوريد 1-بوتيل-3-methylimidazolium (BMIMCl)، ومع ذلك، هذه التفاعلات شرع ف...

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.

توليف فراغي للغاية من 1،6-Ketoesters وساطة من قبل أيوني السوائل: رد فعل ثلاثي مكون تمكين الوصول السريع إلى فئة جديدة من الاسعار المنخفضة الوزن الجزيئي 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 ...

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إعداد واستخدام ثنائي يوديد السمريوم (SMI<sub&gt; 2</sub&gt;) في التركيب العضوي: دور الميكنة من أملاح النيكل وHMPA (II) في رد فعل باربييه السمريوم

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التوليف وتفاعل كيمياء Nanosize أحادية الصوديوم ملح التيتان

This paper describes the synthesis and peroxide-modification of nanosize monosodium titanate (nMST), along with an ion-exchange reaction to load the ...

Synthesis and Exfoliation of Discotic Zirconium Phosphates to Obtain Colloidal Liquid Crystals

التوليف وتقشير من Discotic الزركونيوم الفوسفات للحصول على بلورات الغروية السائل

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

توليف للبرمجة الرئيسية سلسلة اللدائن السائل البلوري باستخدام مرحلتين ثيول-اكريليت رد الفعل

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

توليف الكادميوم خالية من البرنامج النووي العراقي / ZnS الكم النقاط مناسبة للتطبيقات الطبية الحيوية

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

بروتوكول لتوليف<em&gt; أورثو</em&gt; مشتقات الانيلين -trifluoromethoxylated

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

توليف سطحي من المذيلات تشبه دودة من الضوء المرئي وساطة التشتت البلمرة عن طريق Photoredox محفز

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

من جزيئات المواد: هندسة البلورات السائلة الأيونية الجديدة من خلال الربط هالوجين

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

تصنيع واختبار أيروجيلس الحفاز أعدت عن طريق استخراج فوق الحرجة السريع

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

تعزيز السريع نانوبروبي إشارة بتوليف نانوحبيبات الذهب في الموقع

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