Academic literature on the topic 'Macrocyclic muscs'

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Journal articles on the topic "Macrocyclic muscs"

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Williams, Alvin S. "The Synthesis of Macrocyclic Musks." Synthesis 1999, no. 10 (October 1999): 1707–23. http://dx.doi.org/10.1055/s-1999-3581.

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Williams, Alvin S. "ChemInform Abstract: The Synthesis of Macrocyclic Musks." ChemInform 30, no. 49 (June 12, 2010): no. http://dx.doi.org/10.1002/chin.199949256.

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Wang, Quanrui, Sereina Riniker, Philip Kraft, Jie Liu, Vera Hürlimann, Roger Emter, Andreas Natsch, et al. "A New Family of Rigid Dienone Musks Challenges the Perceptive Range of the Human Olfactory Receptor OR5AN1." Synlett 31, no. 10 (March 24, 2020): 972–76. http://dx.doi.org/10.1055/s-0040-1708009.

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A new family of dienone musks was discovered by alkylation of different aldehydes with but-3-en-1-yn-1-yllithium and subsequent domino reaction of a Saucy–Marbet transfer vinylation–Claisen rearrangement with an intramolecular Diels–Alder reaction, and concluding Lewis acid catalyzed double-bond isomerization. The newly synthesized dienone structures possess pleasant musk odors displaying fatty, slightly fruity and green facets. Although the dienone musks were predicted in silico to bind to the OR5AN1 receptor based on QM/MM calculations, they were found to be inactive in the in vitro assay. The latter results suggest that the OR5AN1 receptor is not the prime musk receptor but primarily responsible for the animalic character of certain macrocyclic ketones and nitro musks.
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Ahmed, Lucky, Yuetian Zhang, Eric Block, Michael Buehl, Michael J. Corr, Rodrigo A. Cormanich, Sivaji Gundala, et al. "Molecular mechanism of activation of human musk receptors OR5AN1 and OR1A1 by (R)-muscone and diverse other musk-smelling compounds." Proceedings of the National Academy of Sciences 115, no. 17 (April 9, 2018): E3950—E3958. http://dx.doi.org/10.1073/pnas.1713026115.

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Understanding olfaction at the molecular level is challenging due to the lack of crystallographic models of odorant receptors (ORs). To better understand the molecular mechanism of OR activation, we focused on chiral (R)-muscone and other musk-smelling odorants due to their great importance and widespread use in perfumery and traditional medicine, as well as environmental concerns associated with bioaccumulation of musks with estrogenic/antiestrogenic properties. We experimentally and computationally examined the activation of human receptors OR5AN1 and OR1A1, recently identified as specifically responding to musk compounds. OR5AN1 responds at nanomolar concentrations to musk ketone and robustly to macrocyclic sulfoxides and fluorine-substituted macrocyclic ketones; OR1A1 responds only to nitromusks. Structural models of OR5AN1 and OR1A1 based on quantum mechanics/molecular mechanics (QM/MM) hybrid methods were validated through direct comparisons with activation profiles from site-directed mutagenesis experiments and analysis of binding energies for 35 musk-related odorants. The experimentally found chiral selectivity of OR5AN1 to (R)- over (S)-muscone was also computationally confirmed for muscone and fluorinated (R)-muscone analogs. Structural models show that OR5AN1, highly responsive to nitromusks over macrocyclic musks, stabilizes odorants by hydrogen bonding to Tyr260 of transmembrane α-helix 6 and hydrophobic interactions with surrounding aromatic residues Phe105, Phe194, and Phe207. The binding of OR1A1 to nitromusks is stabilized by hydrogen bonding to Tyr258 along with hydrophobic interactions with surrounding aromatic residues Tyr251 and Phe206. Hydrophobic/nonpolar and hydrogen bonding interactions contribute, respectively, 77% and 13% to the odorant binding affinities, as shown by an atom-based quantitative structure–activity relationship model.
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Sytniczuk, A., M. Milewski, A. Kajetanowicz, and K. Grela. "Preparation of macrocyclic musks via olefin metathesis: comparison with classical syntheses and recent advances." Russian Chemical Reviews 89, no. 4 (March 31, 2020): 469–90. http://dx.doi.org/10.1070/rcr4930.

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Sytniczuk, Adrian, Gwénaël Forcher, Douglas B. Grotjahn, and Karol Grela. "Sequential Alkene Isomerization and Ring-Closing Metathesis in Production of Macrocyclic Musks from Biomass." Chemistry - A European Journal 24, no. 41 (June 21, 2018): 10403–8. http://dx.doi.org/10.1002/chem.201800728.

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Rüedi, Georg, Matthias Nagel, and Hans-Jürgen Hansen. "Three-Carbon Ring Expansion by Cyclopropane Insertion: Macrocyclic Musks from Readily Available C-12 Starting Materials." Organic Letters 6, no. 17 (August 2004): 2989–91. http://dx.doi.org/10.1021/ol0487027.

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Zou, Yue, Halima Mouhib, Wolfgang Stahl, Andreas Goeke, Quanrui Wang, and Philip Kraft. "Efficient Macrocyclization by a Novel Oxy-Oxonia-Cope Reaction: Synthesis and Olfactory Properties of New Macrocyclic Musks." Chemistry - A European Journal 18, no. 23 (April 26, 2012): 7010–15. http://dx.doi.org/10.1002/chem.201200882.

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Zou, Yue, Lijun Zhou, Changming Ding, Quanrui Wang, Philip Kraft, and Andreas Goeke. "A Novel Oxy-Oxonia(Azonia)-CopeReaction: Serendipitous Discovery and Its Application to the Synthesis of Macrocyclic Musks." Chemistry & Biodiversity 11, no. 10 (October 2014): 1608–28. http://dx.doi.org/10.1002/cbdv.201400058.

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Zou Yue, Zou Yue, Lijun Zhou, Changming Ding, Quanrui Wang, Philip Kraft, and Andreas Goeke. "ChemInform Abstract: A Novel Oxy-Oxonia(Azonia)-Cope Reaction: Serendipitous Discovery and Its Application to the Synthesis of Macrocyclic Musks." ChemInform 45, no. 52 (December 11, 2014): no. http://dx.doi.org/10.1002/chin.201452230.

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Dissertations / Theses on the topic "Macrocyclic muscs"

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Raymond, Michaël. "Synthèse de macrocycles par réaction de métathèse et application en débit continu." Thèse, 2016. http://hdl.handle.net/1866/18438.

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La réaction de macrocyclisation par métathèse est une réaction clé en synthèse organique et qui comporte de nombreux défis. Les méthodes traditionnelles de macrocyclisation impliquent par exemple la haute dilution du mélange réactionnel et l’emploie d’une pompe seringue. Dans cette thèse de doctorat, une méthode qui évite l’emploi des techniques de haute dilution a été développée. Cette méthode a été appliquée à la synthèse de cyclophanes macrocycliques. De plus, la synthèse totale de la néomarchantine A, un macrocycle bisbibenzylique, a été réalisée en 12 étapes à partir de produits commercialement disponibles avec un couplage d’Ullmann, un couplage de Wittig et une macrocyclisation par métathèse comme réactions clés. La chimie en débit continu, une méthode facilement applicable en milieu industriel, a été explorée. Cette technologie a été appliquée à l’étape clé de macrocyclisation par métathèse pour la synthèse de la néomarchantine A ainsi que pour la synthèse d’un musc macrocyclique breveté par la compagnie « International Flavors and Fragrances (IFF) ».
The macrocyclic metathesis reaction is a key reaction in organic synthesis and possesses numerous challenges. Traditional methods typically involve high dilution conditions and the use of a syringe pump. In this doctoral thesis, a method that avoids the use of dilution technics has been developed. This method has been applied to the synthesis of macrocyclic cyclophanes. Furthermore, total synthesis of neomarchantin A, a bisbibenzyl macrocycle, has been done in 12 steps from commercially available reagents with an Ullmann coupling, a Wittig coupling and a macrocyclic metathesis reaction as key steps. Continuous flow chemistry, a method easily applicable in an industrial setting, has been explored. This technology was applied to the key macrocyclization step of the neomarchantin A and for the synthesis of a macrocyclic musk patented by International Flavors and Fragrances (IFF).
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Book chapters on the topic "Macrocyclic muscs"

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Tanabe, Yoo. "Synthetic Study on Macrocyclic Musks, Mints, and Jasmine Perfumes Utilizing Ti-Claisen and Aldol Reactions." In ACS Symposium Series, 267–72. Washington, DC: American Chemical Society, 2004. http://dx.doi.org/10.1021/bk-2005-0892.ch025.

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