Au(I)-Catalyzed Cyclization of Methyl 2-(2-Alkynylphenylethynyl) Benzoates to 6H-Dibenzo[c,h]chromen-6-ones and Synthesis of Arnottin I
碩士 === 國立中山大學 === 化學系研究所 === 100 === Gold catalysts have the characteristic of promoting nucleophilic reaction. The cyclization reaction of enediynes catalyzed by gold activated by silver in toluene at 100oC to give 6H-dibenzo[c,h]chromen-6-ones (63), 6H-benzo[c]chromen-6-one (66) and Arnottin I...
Main Authors: | , |
---|---|
Other Authors: | |
Format: | Others |
Language: | zh-TW |
Published: |
2012
|
Online Access: | http://ndltd.ncl.edu.tw/handle/92891328567668102702 |
id |
ndltd-TW-100NSYS5065017 |
---|---|
record_format |
oai_dc |
spelling |
ndltd-TW-100NSYS50650172015-10-13T21:17:53Z http://ndltd.ncl.edu.tw/handle/92891328567668102702 Au(I)-Catalyzed Cyclization of Methyl 2-(2-Alkynylphenylethynyl) Benzoates to 6H-Dibenzo[c,h]chromen-6-ones and Synthesis of Arnottin I 金金屬催化甲基 2-(2-炔基苯乙炔) 苯甲酸之環化反應形成6H-dibenzo[c,h]chromen-6-ones以及Arnottin I之合成 Chia-Ling Hsu 許嘉玲 碩士 國立中山大學 化學系研究所 100 Gold catalysts have the characteristic of promoting nucleophilic reaction. The cyclization reaction of enediynes catalyzed by gold activated by silver in toluene at 100oC to give 6H-dibenzo[c,h]chromen-6-ones (63), 6H-benzo[c]chromen-6-one (66) and Arnottin I (10) is described. Treatment of enediynes (61、65) with 5 mol% of Ph3PAuCl and 10 mol% of AgSbF6 in toluene at 100oC gave 6H-dibenzo[c,h]chromen-6-ones (63) and 6H-benzo[c]chromen-6-one (66) in good yield. In addition to using gold catalyst, electrophilic reagents employed in the reaction caused one cyclization instead of two cyclization. Furthemore, a mechanistic study and GC-MS data showed that the toluene could participate in the reaction. Enediynes (73) can be synthesized by a series of organic synthesis with few steps. Treatment of enediynes (73) with 5 mol% of Ph3PAuCl and 10 mol% of AgSbF6 in toluene at 100oC gave natural product-Arnottin I (10). Ming-Jung Wu 吳明忠 2012 學位論文 ; thesis 228 zh-TW |
collection |
NDLTD |
language |
zh-TW |
format |
Others
|
sources |
NDLTD |
description |
碩士 === 國立中山大學 === 化學系研究所 === 100 === Gold catalysts have the characteristic of promoting nucleophilic reaction. The cyclization reaction of enediynes catalyzed by gold activated by silver in toluene at 100oC to give 6H-dibenzo[c,h]chromen-6-ones (63), 6H-benzo[c]chromen-6-one (66) and Arnottin I (10) is described.
Treatment of enediynes (61、65) with 5 mol% of Ph3PAuCl and 10 mol% of AgSbF6 in toluene at 100oC gave 6H-dibenzo[c,h]chromen-6-ones (63) and 6H-benzo[c]chromen-6-one (66) in good yield. In addition to using gold catalyst, electrophilic reagents employed in the reaction caused one cyclization instead of two cyclization. Furthemore, a mechanistic study and GC-MS data showed that the toluene could participate in the reaction.
Enediynes (73) can be synthesized by a series of organic synthesis with few steps. Treatment of enediynes (73) with 5 mol% of Ph3PAuCl and 10 mol% of AgSbF6 in toluene at 100oC gave natural product-Arnottin I (10).
|
author2 |
Ming-Jung Wu |
author_facet |
Ming-Jung Wu Chia-Ling Hsu 許嘉玲 |
author |
Chia-Ling Hsu 許嘉玲 |
spellingShingle |
Chia-Ling Hsu 許嘉玲 Au(I)-Catalyzed Cyclization of Methyl 2-(2-Alkynylphenylethynyl) Benzoates to 6H-Dibenzo[c,h]chromen-6-ones and Synthesis of Arnottin I |
author_sort |
Chia-Ling Hsu |
title |
Au(I)-Catalyzed Cyclization of Methyl 2-(2-Alkynylphenylethynyl) Benzoates to 6H-Dibenzo[c,h]chromen-6-ones and Synthesis of Arnottin I |
title_short |
Au(I)-Catalyzed Cyclization of Methyl 2-(2-Alkynylphenylethynyl) Benzoates to 6H-Dibenzo[c,h]chromen-6-ones and Synthesis of Arnottin I |
title_full |
Au(I)-Catalyzed Cyclization of Methyl 2-(2-Alkynylphenylethynyl) Benzoates to 6H-Dibenzo[c,h]chromen-6-ones and Synthesis of Arnottin I |
title_fullStr |
Au(I)-Catalyzed Cyclization of Methyl 2-(2-Alkynylphenylethynyl) Benzoates to 6H-Dibenzo[c,h]chromen-6-ones and Synthesis of Arnottin I |
title_full_unstemmed |
Au(I)-Catalyzed Cyclization of Methyl 2-(2-Alkynylphenylethynyl) Benzoates to 6H-Dibenzo[c,h]chromen-6-ones and Synthesis of Arnottin I |
title_sort |
au(i)-catalyzed cyclization of methyl 2-(2-alkynylphenylethynyl) benzoates to 6h-dibenzo[c,h]chromen-6-ones and synthesis of arnottin i |
publishDate |
2012 |
url |
http://ndltd.ncl.edu.tw/handle/92891328567668102702 |
work_keys_str_mv |
AT chialinghsu auicatalyzedcyclizationofmethyl22alkynylphenylethynylbenzoatesto6hdibenzochchromen6onesandsynthesisofarnottini AT xǔjiālíng auicatalyzedcyclizationofmethyl22alkynylphenylethynylbenzoatesto6hdibenzochchromen6onesandsynthesisofarnottini AT chialinghsu jīnjīnshǔcuīhuàjiǎjī22guìjīběnyǐguìběnjiǎsuānzhīhuánhuàfǎnyīngxíngchéng6hdibenzochchromen6onesyǐjíarnottinizhīhéchéng AT xǔjiālíng jīnjīnshǔcuīhuàjiǎjī22guìjīběnyǐguìběnjiǎsuānzhīhuánhuàfǎnyīngxíngchéng6hdibenzochchromen6onesyǐjíarnottinizhīhéchéng |
_version_ |
1718060202603839488 |