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| DC 欄位 | 值 | 語言 |
|---|---|---|
| dc.contributor.advisor | 柳玗珍 | zh_TW |
| dc.contributor.advisor | Woo-Jin Yoo | en |
| dc.contributor.author | 吳淳輔 | zh_TW |
| dc.contributor.author | Chun-Fu Wu | en |
| dc.date.accessioned | 2024-10-14T16:11:28Z | - |
| dc.date.available | 2024-10-15 | - |
| dc.date.copyright | 2024-10-14 | - |
| dc.date.issued | 2024 | - |
| dc.date.submitted | 2024-09-22 | - |
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Chem. 1981, 46, 3936–3938. | - |
| dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/96098 | - |
| dc.description.abstract | 苯環的飽和生物等排體替代物在藥物發現領域中是重點研究方向，並且近幾年來二取代雙環[2.1.1]己烷已被確認為能夠充當鄰位和間位取代苯生物等排體的多功能分子骨架。在我們之前的研究中，我們合成了1-取代雙環[2.1.1]己烷-5-醇，這些化合物可以作為鄰位酚類生物等排體。然而，在我們的官能化研究中，我們發現這些化合物無法忍受強酸和強鹼的條件，因此限制了我們合成若干具有生物活性的分子骨架。為此，我們假設將醇基重新定位到橋頭位置希望可以提高雙環醇的穩定性。在本論文中，我們概述了通過兩類二碘化釤介導的還原環化反應合成一系列2-取代雙環[2.1.1]己烷-1-醇的方法，以充當鄰位酚類生物等排體。 | zh_TW |
| dc.description.abstract | The substitution of benzene rings with saturated bioisosteres is an area of focus in drug discovery, and disubstituted bicyclo[2.1.1]hexanes have been identified as versatile molecular scaffolds capable of serving as ortho- and meta-substituted benzene bioisosteres. In our previous work, we synthesized 1-substituted bicyclo[2.1.1]hexan-5-ols, which could act as ortho-phenolic bioisosteres. However, during our functionalization studies, we found that these compounds could not endure strong acidic and basic conditions, which limits our ability to synthesize saturated version of several bioactive molecules. Therefore, we supposed that relocating the alcohol group to the bridgehead position could enhance the stability of the bicyclic alcohol. In this thesis, we outline the synthesis of a range of 2-substituted bicyclo[2.1.1]hexan-1-ols via two categories of SmI2-mediated reductive cyclization reactions for acting as ortho-phenolic bioisosteres. | en |
| dc.description.provenance | Submitted by admin ntu (admin@lib.ntu.edu.tw) on 2024-10-14T16:11:28Z No. of bitstreams: 0 | en |
| dc.description.provenance | Made available in DSpace on 2024-10-14T16:11:28Z (GMT). No. of bitstreams: 0 | en |
| dc.description.tableofcontents | Abstract.....i
摘要.....ii Chapter 1 Introduction.....1 1.1 Definition and history of bioisoterism.....1 1.2 Examples of classical bioisosteres.....5 1.3 Examples of rigid hydrocarbons as benzene bioisosteres.....8 1.4 Synthesis of bicyclo[2.1.1]hexane as ortho-substituted benzene bioisostere.....12 1.5 Introduction of SmI2 mediated cross coupling reaction.....17 Chapter 2 Experimental Design.....21 Chapter 3 Results and Discussion.....24 3.1 Starting material synthesis and optimization for ketyl-olefin cyclization.....24 3.2 Substrate scope for ketyl-olefin cyclization.....28 3.3 Starting material synthesis and optimization for the Barbier reaction.....30 3.4 Substrate scope for the Barbier reaction.....32 3.5 Starting material synthesis and optimization for the Reformastky-type reaction.....35 3.6 Conclusion.....38 Chapter 4 Experimental Section.....39 4.1 General Information.....39 4.2 Preparation of aldehyde 60.....40 4.3 General procedure for the synthesis of 54a-54l via olefination reactions.....41 4.4 Substrate scope for the synthesis of 56a-h (General Procedure A).....48 4.5 Substrate scope for the synthesis of 56h-l (General Procedure B).....51 4.6 General procedure for the synthesis of 66a-n via addition reactions.....54 4.7 Substrate scope for the synthesis of 55a-n (General Procedure C).....66 4.8 Preparation of cyclobutanones 68 for Reformatsky reaction.....75 Reference.....79 Chapter 5 Supplementary Information.....87 5.1 NMR spectra.....87 | - |
| dc.language.iso | en | - |
| dc.title | 藉由二碘化釤介導的還原環化反應合成 2-取代雙環[2.1.1]己-1-醇 | zh_TW |
| dc.title | Synthesis of 2-Substituted Bicyclo[2.1.1]hexan-1-ols via SmI2-Mediated Reductive Cyclization Reactions | en |
| dc.type | Thesis | - |
| dc.date.schoolyear | 113-1 | - |
| dc.description.degree | 碩士 | - |
| dc.contributor.oralexamcommittee | 羅禮強;陳國庭 | zh_TW |
| dc.contributor.oralexamcommittee | Lee-Chiang Lo;Kuo-Ting Chen | en |
| dc.subject.keyword | 二取代的雙環[2.1.1]己烷,苯生物等排體,2-取代的雙環[2.1.1]己烷-1-醇,鄰位酚衍生物,二碘化釤介導的還原環化反應, | zh_TW |
| dc.subject.keyword | Disubstituted bicyclo[2.1.1]hexanes,Benzene bioisosteres,2-Substituted bicyclo[2.1.1]hexan-1-ols,Ortho-phenolic,SmI2-mediated reductive cyclization, | en |
| dc.relation.page | 189 | - |
| dc.identifier.doi | 10.6342/NTU202404379 | - |
| dc.rights.note | 同意授權(全球公開) | - |
| dc.date.accepted | 2024-09-23 | - |
| dc.contributor.author-college | 理學院 | - |
| dc.contributor.author-dept | 化學系 | - |
| 顯示於系所單位： | 化學系 | |
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