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You searched for subject:(Calone 1951). Showing records 1 – 3 of 3 total matches.

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1. Cacciuttolo, Bastien. Formation de composés polycycliques par activation de doubles liaisons : approche catalytique intra et intermoléculaire de réactions de type Friedel-Crafts : applications au domaine des arômes et parfums : Non disponible.

Degree: Docteur es, Chimie, 2013, Nice

L’utilisation de méthodologies de synthèse toujours plus performantes et respectueuses de l’environnement est un axe de recherche majeur de la chimie moderne. L’apport de la catalyse, avec l’utilisation de superacides de Lewis, a permis d’améliorer de nombreux processus synthétiques. Nous avons pu développer dans ce manuscrit des réactions de cycloisomérisation de type réaction de Friedel-Crafts qui donnent accès à un ensemble de structures polycycliques intéressantes avec de bons rendements et sélectivités. L’utilisation d’une quantité catalytique, entre 1 et 10 mol% de Bi(OTf)3, permet l’activation d’oléfines et d’allènes non activés ainsi que de systèmes 1,3-diéniques. Ce type de méthodologie, à économie d’atomes maximale, a permis de limiter la formation de sous-produits, le catalyseur pouvant être recyclé et réutilisé sans perte d’activité. Des approches intra- et intermoléculaires, des réactions cascades et tandems ainsi qu’une étude mécanistique ont été effectuées afin de mieux comprendre la réactivité et ses limitations, et ainsi atteindre une plus large gamme de structures. Les méthodologies développées ont été appliquées au domaine des arômes et parfums pour la synthèse d’analogues de la Calone 1951®, de chromanes, d’indanes et de tétralines fonctionnalisés, posant les bases de travaux futurs pour une meilleur compréhension des relations structures-odeurs

Efficient and ecofriendly synthetic methodologies have always constituted an important area of research in modern organic chemistry. Lewis superacid catalysis has contributed in the improvement of many synthetic processes. We have developed some cycloisomerization reactions including Friedel-Crafts type reaction, giving access to a set of interesting polycyclic structures with good yields and selectivities. The use of a catalytic amount of Bi(OTf)3 (1 to 10 mol%), has allowed the activation of olefins, non-activated allenes and of 1,3-dienic systems. This atom economy methodology can prevent the formation of by-products and the catalyst can be recycled without loss of activity. Intra- and intermolecular approaches, tandem and cascades reactions, as well as mechanistic studies were conducted to enable a better understanding of the reactivity and its limitations to reach a wider range of structures. The developed methodologies were applied to the field of flavors and fragrances in the synthesis of Calone 1951® analogues, and for the preparation of chromans, indanes and tetralins type functionalized structures, for a better understanding of the structure/odor relationship.

Advisors/Committee Members: Duñach-Clinet, Elisabet (thesis director).

Subjects/Keywords: Friedel-Crafts; Cyclisation; Catalyse; Triflate de bismuth; Oléfine non activée; Allène; Diène-1,3; Calone 1951; Chromane; Indane; Tétraline; Benzosubérane; Friedel-Crafts; Cyclization; Catalysis; Bismuth triflate; Unactivated olefine; Allene; 1,3-diene; Calone 1951; Chromane; Indane; Tetraline; Benzosuberane; 540

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Cacciuttolo, B. (2013). Formation de composés polycycliques par activation de doubles liaisons : approche catalytique intra et intermoléculaire de réactions de type Friedel-Crafts : applications au domaine des arômes et parfums : Non disponible. (Doctoral Dissertation). Nice. Retrieved from http://www.theses.fr/2013NICE4009

Chicago Manual of Style (16th Edition):

Cacciuttolo, Bastien. “Formation de composés polycycliques par activation de doubles liaisons : approche catalytique intra et intermoléculaire de réactions de type Friedel-Crafts : applications au domaine des arômes et parfums : Non disponible.” 2013. Doctoral Dissertation, Nice. Accessed August 04, 2020. http://www.theses.fr/2013NICE4009.

MLA Handbook (7th Edition):

Cacciuttolo, Bastien. “Formation de composés polycycliques par activation de doubles liaisons : approche catalytique intra et intermoléculaire de réactions de type Friedel-Crafts : applications au domaine des arômes et parfums : Non disponible.” 2013. Web. 04 Aug 2020.

Vancouver:

Cacciuttolo B. Formation de composés polycycliques par activation de doubles liaisons : approche catalytique intra et intermoléculaire de réactions de type Friedel-Crafts : applications au domaine des arômes et parfums : Non disponible. [Internet] [Doctoral dissertation]. Nice; 2013. [cited 2020 Aug 04]. Available from: http://www.theses.fr/2013NICE4009.

Council of Science Editors:

Cacciuttolo B. Formation de composés polycycliques par activation de doubles liaisons : approche catalytique intra et intermoléculaire de réactions de type Friedel-Crafts : applications au domaine des arômes et parfums : Non disponible. [Doctoral Dissertation]. Nice; 2013. Available from: http://www.theses.fr/2013NICE4009


RMIT University

2. Plummer, C. The chemical synthesis of aliphatic benzo[b][1,4]dioxepin-3-one analogues related to synthetic marine odorants.

Degree: 2016, RMIT University

Odour discrimination is a combinatorial phenomenon, as odorant molecules are known to bind to multiple olfactory receptors. It is also considered that the absolute configuration of a molecule is of crucial importance in determining the human perception of odour. Additionally, it is also recognised that a substance evokes a sense of smell provided that its molecular shape is compatible with the complementary space within the olfactory receptor. Since the benzo[b][1,4]dioxepin-3-one scaffold represents the essential structural characteristics of the synthetic marine odorant family, we were therefore interested in the effect of modulating the molecular shape via an aromatic/aliphatic ring exchange. By the substitution of the aromatic functionality with a saturated ring counterpart we endeavoured to discover the molecular interactions of the carbocyclic ring systems with olfactory receptor sites, including any potential chiral interactions occurring within the receptor(s). Our initial results revealed that an aromatic ring system was necessary for binding to the marine odorant receptor(s) and that the addition of an alkene or methyl substituent had little effect on receptor affinity. The synthesised aliphatic benzo[b][1,4]dioxepin-3-one analogues instead exhibited a plethora of odorant descriptors and consequently it was speculated that perhaps altogether new odorant families could be targeted by further chemical synthesis. It was also questioned if the fusion of 1,4-dioxepan-6-one heterocyclic rings onto naturally occurring terpenoid odorants could merge/synergise existing fragrance classes. The chemical synthesis and olfactory characterisation of a variety of aliphatic benzo[b][1,4]dioxepin-3-one analogues, as well as a series of 2-substituted and 2,3-annulated 1,4-dioxepan-6-one analogues is hereby reported.

Subjects/Keywords: Fields of Research; Chemistry; Synthesis; Fragrance; Benzodioxepinone; Calone 1951; Dioxepanone; Heterocycle; Organic synthesis; Chemical synthesis; Odorant; Fused-ring system; Structure-activity relationship

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Plummer, C. (2016). The chemical synthesis of aliphatic benzo[b][1,4]dioxepin-3-one analogues related to synthetic marine odorants. (Thesis). RMIT University. Retrieved from http://researchbank.rmit.edu.au/view/rmit:161628

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

Plummer, C. “The chemical synthesis of aliphatic benzo[b][1,4]dioxepin-3-one analogues related to synthetic marine odorants.” 2016. Thesis, RMIT University. Accessed August 04, 2020. http://researchbank.rmit.edu.au/view/rmit:161628.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

Plummer, C. “The chemical synthesis of aliphatic benzo[b][1,4]dioxepin-3-one analogues related to synthetic marine odorants.” 2016. Web. 04 Aug 2020.

Vancouver:

Plummer C. The chemical synthesis of aliphatic benzo[b][1,4]dioxepin-3-one analogues related to synthetic marine odorants. [Internet] [Thesis]. RMIT University; 2016. [cited 2020 Aug 04]. Available from: http://researchbank.rmit.edu.au/view/rmit:161628.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Plummer C. The chemical synthesis of aliphatic benzo[b][1,4]dioxepin-3-one analogues related to synthetic marine odorants. [Thesis]. RMIT University; 2016. Available from: http://researchbank.rmit.edu.au/view/rmit:161628

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation


RMIT University

3. Drevermann, B. Marine fragrance chemistry : synthesis, olfactory characterisation and structure-odour-relationships of benzodioxepinone analogues.

Degree: 2007, RMIT University

Calone 1951® (7-methyl-2H-1,5-benzodioxepin-3(4H)-one) is renowned in the fragrance industry for its distinct marine odour and offers an interesting molecular framework for structure-odour-relationship (SOR) research. Limited olfactory reports on 7-membered benzodioxepine analogues with modification influenced by functionality, polarity, and ring size, prompted us to construct a range of aromatic and C-3 substituted structures for olfactory evaluation. Incorporation of a diverse range of functionality contributes valuable information on the molecular aspects that determine the archetypal marine character of Calone 1951®. Here we present the preparation of Calone 1951® analogues including spectroscopic and olfactory details to contribute to the sparse marine fragrance arena. In these studies pertaining to the odour properties of benzodioxepinone systems, we considered the mod ification of substitution and functionality on the aromatic ring in the context of qualitative olfactory analysis. Application of the patented Williamson and Dieckmann reaction pathways resulted in construction of the benzodioxepinone molecule. Preparation of aryl-substituted benzodioxepinones required introduction of an alternate broadly applicable synthetic pathway due to the diverse nature of the introduced substituents. Limitations of the patented approach led to incorporation of a simple but novel methodology applied to the same range of substituted catechol reagents for synthesis of the benzodioxepinone skeleton and an overview of comparable yields. Single-step mechanisms were also successfully applied to contribute to the repertoire of benzodioxepin(on)e structures prepared for olfactory analysis. Semi-empirical models of the synthesised data set were generated and evaluated in light of previous research undertaken by Archer and Claret and related to the olfactory characteristics of each compound. Evaluation of the models with corresponding olfactory information revealed that functionality and ring size contribute significantly to the conformation adopted by the benzodioxepinone species and therefore the olfactory character of the molecule. It is evident from our observations that aromatic ring substitution and functional alteration of the cyclic ketone modifies the perceived odour of Calone 1951®. Structural modification overall led to a decrease in odour potency. The presence of the aromatic methyl substituent in Calone 1951® reinforces, but is not critical for, the marine tonality. Modification of the ketone of Calone 1951® led to significant deviation in character from the prototypical marine odour.

Subjects/Keywords: Fields of Research; Calone 1951®; benzodioxepinone; structure-odour-relationships (SORs); marine; odourants

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APA · Chicago · MLA · Vancouver · CSE | Export to Zotero / EndNote / Reference Manager

APA (6th Edition):

Drevermann, B. (2007). Marine fragrance chemistry : synthesis, olfactory characterisation and structure-odour-relationships of benzodioxepinone analogues. (Thesis). RMIT University. Retrieved from http://researchbank.rmit.edu.au/view/rmit:6655

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Chicago Manual of Style (16th Edition):

Drevermann, B. “Marine fragrance chemistry : synthesis, olfactory characterisation and structure-odour-relationships of benzodioxepinone analogues.” 2007. Thesis, RMIT University. Accessed August 04, 2020. http://researchbank.rmit.edu.au/view/rmit:6655.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

MLA Handbook (7th Edition):

Drevermann, B. “Marine fragrance chemistry : synthesis, olfactory characterisation and structure-odour-relationships of benzodioxepinone analogues.” 2007. Web. 04 Aug 2020.

Vancouver:

Drevermann B. Marine fragrance chemistry : synthesis, olfactory characterisation and structure-odour-relationships of benzodioxepinone analogues. [Internet] [Thesis]. RMIT University; 2007. [cited 2020 Aug 04]. Available from: http://researchbank.rmit.edu.au/view/rmit:6655.

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

Council of Science Editors:

Drevermann B. Marine fragrance chemistry : synthesis, olfactory characterisation and structure-odour-relationships of benzodioxepinone analogues. [Thesis]. RMIT University; 2007. Available from: http://researchbank.rmit.edu.au/view/rmit:6655

Note: this citation may be lacking information needed for this citation format:
Not specified: Masters Thesis or Doctoral Dissertation

.