Side-Chain Modification and “Grafting Onto” via Olefin Cross-Metathesis

2012 ◽  
Vol 33 (23) ◽  
pp. 2023-2028 ◽  
Author(s):  
Lucas Montero de Espinosa ◽  
Kristian Kempe ◽  
Ulrich S. Schubert ◽  
Richard Hoogenboom ◽  
Michael A. R. Meier
Keyword(s):  
Side Chain ◽  
Cross Metathesis ◽  
Grafting Onto

scholarly journals Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

2018 ◽  
Vol 14 ◽  
pp. 2737-2744 ◽  
Author(s):  
Jacqueline Pollini ◽  
Valentina Bragoni ◽  
Lukas J Gooßen
Keyword(s):  
First Generation ◽  
Anacardic Acid ◽  
Side Chain ◽  
Tyrosinase Inhibitor ◽  
Target Compound ◽  
Selective Precipitation ◽  
Acid Component ◽  
Cross Metathesis ◽  
Cashew Nutshell Liquid ◽  
Bond Isomers

A convenient and sustainable three-step synthesis of the tyrosinase inhibitor 2-hydroxy-6-tridecylbenzoic acid was developed that starts directly from the anacardic acid component of natural cashew nutshell liquid (CNSL). Natural CNSL contains 60–70% of anacardic acid as a mixture of several double bond isomers. The anacardic acid component was converted into a uniform starting material by ethenolysis of the entire mixture and subsequent selective precipitation of 6-(ω-nonenyl)salicylic acid from cold pentane. The olefinic side chain of this intermediate was elongated by its cross-metathesis with 1-hexene using a first generation Hoveyda–Grubbs catalyst, which was reused as precatalyst in a subsequent hydrogenation step. Overall, the target compound was obtained in an overall yield of 61% based on the unsaturated anacardic acid content and 34% based on the crude CNSL.

scholarly journals Synthesis of a Poly(3-dodecylthiophene) Bearing Aniline Groups for the Covalent Functionalization of Carbon Nanotubes

Reactions ◽  
2021 ◽  
Vol 2 (4) ◽  
pp. 473-485
Author(s):  
Felipe Wasem Klein ◽  
Jean-Philippe Lamps ◽  
Matthieu Paillet ◽  
Pierre Petit ◽  
Philippe J. Mésini
Keyword(s):  
Carbon Nanotubes ◽  
Single Walled Carbon Nanotubes ◽  
Polymer Chains ◽  
Side Chain ◽  
Covalent Functionalization ◽  
One Step ◽  
Diazonium Coupling ◽  
Functionalization Of Carbon Nanotubes ◽  
Walled Carbon Nanotubes ◽  
Grafting Onto

The functionalization of carbon nanotubes by polymers necessitates two steps, first their modification by oxidizing them or by covalently attaching small compounds to them, then the growth of the polymer chains from these anchors or their grafting onto them. In order to better control the process and the rate of functionalization, we develop polymers able to covalently react with the carbon nanotubes by their side chains in one step. We describe the synthesis of a copolymer of dodecylthiophene and its analogue bearing an aniline group at the end of the dodecyl side chain. This copolymer can functionalize single-walled carbon nanotubes (SWNTs) non-covalently and disperse more SWNTs than its hexyl analogues. UV-Vis and fluorescence spectroscopies show that in these non-covalent hybrids, the polymer forms p-stacked aggregates on the SWNTs. The non-covalent hybrids can be transformed into covalent ones by diazonium coupling. In these covalent hybrids the polymer is no longer p-stacked. According to Raman spectroscopy, the conformation of the poly(3-hexylthiophene) backbone is more ordered in the non-covalent hybrids than in the covalent ones.

scholarly journals Synthesis and investigation of a self-assembled hydrogel based on hydroxyethyl cellulose and its in vitro ibuprofen drug release characteristics

RSC Advances ◽  
2017 ◽  
Vol 7 (16) ◽  
pp. 9500-9511 ◽  
Author(s):  
Nan Sun ◽  
Ting Wang ◽  
Xiufeng Yan
Keyword(s):  
Drug Release ◽  
Inclusion Complexes ◽  
Hydroxyethyl Cellulose ◽  
Side Chain ◽  
Self Assembled ◽  
Grafting Onto

IBU is solubilized and encapsulated by β-CDP. Then C12 side-chain grafting onto HEC forms inclusion complexes with the cavities of β-CDP in β-CDP/IBU through host–guest interactions to form a new self-assembled hydrogel gel-(β)CDP-HEC/IBU.

Side-Chain Truncation of Apicularen A by Olefin Cross-Metathesis with Ethylene

2007 ◽  
Vol 70 (8) ◽  
pp. 1377-1379 ◽  
Author(s):  
Larissa Jundt ◽  
Gerhard Höfle
Keyword(s):  
Side Chain ◽  
Cross Metathesis ◽  
Apicularen A

scholarly journals 4-[(E)-4-Hydroxybut-2-en-1-yl]-2-methoxyphenol

IUCrData ◽  
2016 ◽  
Vol 1 (6) ◽  
Author(s):  
Kyle S. Knight ◽  
Michael C. Orick
Keyword(s):  
Hydrogen Bonds ◽  
Aromatic Ring ◽  
Dihedral Angle ◽  
Title Compound ◽  
Side Chain ◽  
Metathesis Reaction ◽  
Cross Metathesis ◽  
Compound C

The title compound, C11H14O3, was synthesized by a cross-metathesis reaction. The dihedral angle between the aromatic ring and the butenol side chain is 30.2 (2)°. In the crystal, inversion dimers are formed through O—H...O hydrogen bonds and these are linked into chains by additional O—H...O contacts. These chains are linked into sheets in thebcplane by C—H...O hydrogen bonds.

scholarly journals Synthesis and Glycosidase Inhibition of Broussonetine M and Its Analogues

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3712 ◽  
Author(s):  
Wu ◽  
Kinami ◽  
Kato ◽  
Li ◽  
Fleet ◽  
...  
Keyword(s):  
Natural Product ◽  
Hydroxyl Group ◽  
Side Chain ◽  
Alkyl Side Chain ◽  
Asymmetric Allylation ◽  
Pyrrolidine Ring ◽  
Cross Metathesis ◽  
Similar Strategy ◽  
Key Steps ◽  
Glycosidase Inhibition

Cross-metathesis (CM) and Keck asymmetric allylation, which allows access to defined stereochemistry of a remote side chain hydroxyl group, are the key steps in a versatile synthesis of broussonetine M (3) from the d-arabinose-derived cyclic nitrone 14. By a similar strategy, ent-broussonetine M (ent-3) and six other stereoisomers have been synthesized, respectively, starting from l-arabino-nitrone (ent-14), l-lyxo-nitrone (ent-3-epi-14), and l-xylo-nitrone (2-epi-14) in five steps, in 26%–31% overall yield. The natural product broussonetine M (3) and 10’-epi-3 were potent inhibitors of β-glucosidase (IC50 = 6.3 μM and 0.8 μM, respectively) and β-galactosidase (IC50 = 2.3 μM and 0.2 μM, respectively); while their enantiomers, ent-3 and ent-10’-epi-3, were selective and potent inhibitors of rice α-glucosidase (IC50 = 1.2 μM and 1.3 μM, respectively) and rat intestinal maltase (IC50 = 0.29 μM and 18 μM, respectively). Both the configuration of the polyhydroxylated pyrrolidine ring and C-10’ hydroxyl on the alkyl side chain affect the specificity and potency of glycosidase inhibition.

Synthesis and properties of a rod-g-rod bottlebrush with a semirigid mesogen-jacketed polymer as the side chain

2014 ◽  
Vol 5 (17) ◽  
pp. 4948-4956 ◽  
Author(s):  
Hai-Jian Tian ◽  
Wei Qu ◽  
Yu-Feng Zhu ◽  
Zhihao Shen ◽  
Xing-He Fan
Keyword(s):  
Chain Length ◽  
Side Chain ◽  
Side Chains ◽  
Side Chain Length ◽  
Grafting Onto

A series of bottlebrushes, PPLG-g-PMPCS, with an α-helical rigid backbone and mesogen-jacketed rigid side chains were synthesized by the “grafting onto” method. The conformation of the bottlebrush changes from a cylinder to an ellipsoid with increasing side-chain length.

Electroluminescent properties of side-chain naphthalimide-derivated polymers

1998 ◽  
Vol 95 (6) ◽  
pp. 1351-1354 ◽  
Author(s):  
C.-M. Bouché ◽  
P. Le Barny ◽  
H. Facoetti ◽  
F. Soyer ◽  
P. Robin
Keyword(s):  
Side Chain
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