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Tetrahedron

Reactions of ketene acetals-14 The use of simple mixed vinylketene acetals in the annulation of quinones

J Savard, P Brassard

文献索引：Savard, Jacques; Brassard, Paul Tetrahedron, 1984 , vol. 40, # 18 p. 3455 - 3464

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被引用次数: 157

摘要

α, β-β, γ-unsaturated esters can be converted by strong base and chlorotrimethylsilane to the corresponding mixed vinylketene acetals which are shown to be particularly useful and generally applicable reagents for the regiospecific annulation of halogenoquinones. The reaction proceeds readily with a variety of substrates including benzoquinones.

2-氯-1,4-萘醌结构式

2-氯-1,4-萘醌

1,2-dimethoxy-1-trimethylsilyloxy-1,3-butadiene结构式

1,2-dimethoxy-1...

~3%

1-羟基-2-甲氧基蒽醌结构式

1-羟基-2-甲氧基蒽醌

1,2-Dimethoxyanthracene-9,10-dione结构式

1,2-Dimethoxyan...

chlorojuglone结构式

(1-methoxy-2-methylbuta-1,3-dienoxy)-trimethylsilane结构式

(1-methoxy-2-me...

~32%

1,5-dihydroxy-2-methylanthracene-9,10-dione结构式

1,5-dihydroxy-2...

未登录结构式

1-溴-2-丁烯结构式

氯甲酸甲酯结构式

氯甲酸甲酯

~60%

3-Butenoic acid, 2-Methyl-, Methyl ester结构式

3-Butenoic acid...

2、6一二氯-P-苯醌结构式

2、6一二氯-P-苯醌

Brassard's diene结构式

Brassard's diene

~5%

3-氯-5-羟基-7-甲氧基萘醌结构式

3-氯-5-羟基-7-甲氧基萘醌

2-chloro-6,8-dimethoxynaphthalene-1,4-dione结构式

2-chloro-6,8-di...

未登录结构式

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~82%

9,10-Anthracenedione,1,5,8-trihydroxy-3- methyl-结构式

9,10-Anthracene...

1,4-dihydroxy-8-methoxy-6-methylanthraquinone结构式

1,4-dihydroxy-8...

2-chloro-8-hydroxynaphthalene-1,4-dione结构式

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~3%

大黄酚结构式

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione结构式

8-hydroxy-1-met...

2-chloro-8-hydroxynaphthalene-1,4-dione结构式

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~3%

大黄酚结构式

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione结构式

8-hydroxy-1-met...

详细

3-chloro-5-methoxy-1,4-naphthoquinone结构式

3-chloro-5-meth...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~43%

8-Methyl Chrysophanol结构式

8-Methyl Chryso...

1,8-二甲氧基-3-甲基蒽酮结构式

1,8-二甲氧基-3-甲基蒽酮

3-chloro-5-methoxy-1,4-naphthoquinone结构式

3-chloro-5-meth...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~49%

8-Methyl Chrysophanol结构式

8-Methyl Chryso...

1,8-二甲氧基-3-甲基蒽酮结构式

1,8-二甲氧基-3-甲基蒽酮

2-chloro-8-hydroxy-6-methyl-1,4-naphthoquinone结构式

2-chloro-8-hydr...

Brassard's diene结构式

Brassard's diene

~9%

大黄素甲醚结构式

大黄素甲醚

1-Hydroxy-3,8-dimethoxy-6-methylanthraquinone结构式

1-Hydroxy-3,8-d...

2-氯-1,4-萘醌结构式

2-氯-1,4-萘醌

Brassard's diene结构式

Brassard's diene

~99%

1-Hydroxy-3-methoxy-9,10-anthraquinone结构式

1-Hydroxy-3-met...

chlorojuglone结构式

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~56%

1,5-Dihydroxy-3-methylanthraquinone结构式

1,5-Dihydroxy-3...

3-氯-5-羟基-7-甲氧基萘醌结构式

3-氯-5-羟基-7-甲氧基萘醌

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~66%

大黄素甲醚结构式

大黄素甲醚

1-hydroxy-6,8-dimethoxy-3-methylanthracene-9,10-dione结构式

1-hydroxy-6,8-d...

详细

2-chloro-8-hydroxy-6-methyl-1,4-naphthoquinone结构式

2-chloro-8-hydr...

Brassard's diene结构式

Brassard's diene

~73%

大黄素甲醚结构式

大黄素甲醚

1-Hydroxy-3,8-dimethoxy-6-methylanthraquinone结构式

1-Hydroxy-3,8-d...

3-氯-5-羟基-7-甲氧基萘醌结构式

3-氯-5-羟基-7-甲氧基萘醌

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~8%

大黄素甲醚结构式

大黄素甲醚

1-hydroxy-6,8-dimethoxy-3-methylanthracene-9,10-dione结构式

1-hydroxy-6,8-d...

详细

2-氯-1,4-萘醌结构式

2-氯-1,4-萘醌

1,2-dimethoxy-1-trimethylsilyloxy-1,3-butadiene结构式

1,2-dimethoxy-1...

~75%

1-羟基-2-甲氧基蒽醌结构式

1-羟基-2-甲氧基蒽醌

1,2-Dimethoxyanthracene-9,10-dione结构式

1,2-Dimethoxyan...

2-氯-1,4-萘醌结构式

2-氯-1,4-萘醌

(1-methoxy-2-methylbuta-1,3-dienoxy)-trimethylsilane结构式

(1-methoxy-2-me...

~54%

1-羟基-2-甲基蒽醌结构式

1-羟基-2-甲基蒽醌

未登录结构式

2-chloro-8-hydroxynaphthalene-1,4-dione结构式

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~21%

大黄酚结构式

未登录结构式

2-chloro-8-hydroxynaphthalene-1,4-dione结构式

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~64%

大黄酚结构式

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione结构式

8-hydroxy-1-met...

2-chloro-8-hydroxynaphthalene-1,4-dione结构式

2-chloro-8-hydr...

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~62%

大黄酚结构式

8-hydroxy-1-methoxy-3-methylanthracene-9,10-dione结构式

8-hydroxy-1-met...

详细

2-氯-1,4-萘醌结构式

2-氯-1,4-萘醌

(1-methoxy-3-methylbuta-1,3-dienyloxy)-trimethylsilane结构式

(1-methoxy-3-me...

~92%

Pachybasin结构式

未登录结构式

2、6一二氯-P-苯醌结构式

2、6一二氯-P-苯醌

Brassard's diene结构式

Brassard's diene

~92%

3-氯-5-羟基-7-甲氧基萘醌结构式

3-氯-5-羟基-7-甲氧基萘醌

2-chloro-6,8-dimethoxynaphthalene-1,4-dione结构式

2-chloro-6,8-di...

2-chloro-8-hydroxynaphthalene-1,4-dione结构式

2-chloro-8-hydr...

Brassard's diene结构式

Brassard's diene

~53%

1,8-dihydroxy-3-methoxyanthracene-9,10-dione结构式

1,8-dihydroxy-3...

2-chloro-5-methoxycyclohexa-2,5-diene-1,4-dione结构式

2-chloro-5-meth...

Brassard's diene结构式

Brassard's diene

~20%

5-hydroxy-2,7-dimethoxy-naphthalene-1,4-dione结构式

5-hydroxy-2,7-d...

5-hydroxy-2,7-dimethoxy-naphthalene-1,4-dione结构式

5-hydroxy-2,7-d...

碘甲烷结构式

~%

2,5,7-三甲氧基-[1,4]萘醌结构式

2,5,7-三甲氧基-[1,4]萘醌

Preparation of anthraquinones from 10-hydroxy-9-anthraceneca...

[Bhawal, Baburao M.; Khanapure, Subhash P.; Zhang, Hongming; Biehl, Edward R. Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2846 - 2849]

Obtention of Anthraquinones by Selective Oxidation of the Co...

[Anastasia; Allevi; Bettini; Fiecchi; Sanvito Synthesis, 1990 , # 11 p. 1083 - 1084]

Obtention of Anthraquinones by Selective Oxidation of the Co...

[Anastasia; Allevi; Bettini; Fiecchi; Sanvito Synthesis, 1990 , # 11 p. 1083 - 1084]

Monoketale von 1.2??Diketonen. Ein Beitrag zur Theorie der B...

[Kuhn,R.; Trischmann,H. Chemische Berichte, 1961 , vol. 94, p. 2258 - 2263]

Monoketale von 1.2??Diketonen. Ein Beitrag zur Theorie der B...

[Kuhn,R.; Trischmann,H. Chemische Berichte, 1961 , vol. 94, p. 2258 - 2263]