异黄酮类化合物合成新方法及3，4-二氢-2（1H）-喹啉酮衍生物合成新方法研究
摘要
异黄酮类化合物是黄酮家族中一个十分重要的亚类，是许多中草药的有效成分之一，具有广泛的生理和药理活性，如抗癌、抗菌、抗炎及对心血管系统、内分泌系统、免疫系统的改善作用等，某些以异黄酮类成分为主的制剂经临床试用有效已作为成药上市。3，4-二-氢-2(1H)喹啉酮衍生物是重要的医药及化工中间体，可用于合成血栓药、消炎药、强心剂、治疗心脑血管药、抗癌药等，以其为中间体合成的药物已被用作治疗性药物上市。
本论文包括两个部分，第一部分研究了异黄酮类化合物的合成新方法，第二部分研究了3，4-二氢-2(1H)喹啉酮衍生物的合成新方法。
在第一部分，综述了异黄酮化合物的合成方法，在此基础上，自行设计了合成路线，经赫氏(Hoesch)或酰化反应、脱甲基化、环化和脱甲基化反应合成了染料木素及其衍生物、大豆黄素及其衍生物、5，7-二羟基异黄酮及其衍生物以及6-溴-4′，7-二甲氧基异黄酮，就工艺条件进行了探讨，得到了最佳反应条件。
文献报道的染料木素及5，7-二羟基异黄酮的合成反应中，一般采用1，3，5-三羟基苯为原料，总收率在45-50％左右。首先，本文中在原料的选择上，以价格低廉且供应充足的1，3，5-三甲氧基苯为原料，经苯基苄基酮路线环合得到4′，5，7-三甲氧基异黄酮或5，7-二甲氧基异黄酮后，直接以氢溴酸／相转移催化剂或氢溴酸为脱甲基反应体系，一次性脱去全部甲基，得到染料木素或5，7-二羟基异黄酮，采用新工艺路线后，不仅降低了成本，且可将总收率提高到60-75％，还可以通过对脱甲基试剂的调整及反应条件的控制，得到4′，5，7-三甲氧基异黄酮和5，7-二甲氧基异黄酮的部分脱甲基产物。
其次，在合成6-溴-4′，7-二甲氧基异黄酮的过程中得到了新化合物2-羟基-4，4′-二甲氧基-5-溴脱氧安息香和6-溴-4′，7-二甲氧基异黄酮(经检索，无相关报道)，发现了在6-溴-4′，7-二甲氧基异黄酮在脱甲基过程中存在脱溴现象，并从机理上进行了分析。
再次，根据文献报道，脱甲基试剂中只有氢碘酸可一次性脱去全部甲基，而本文中采用氢溴酸／相转移催化剂(四正丁基溴化铵、苄基三乙基氯化铵或三甲基十六烷基溴化铵等)或氢溴酸为脱甲基反应体系，一次性脱去全部甲基，直接
浙江大学博士学位论文
摘要
得到染料木素、大豆黄素和5，7一二轻基异黄酮，具有首创性，不仅可以脱去全部
甲基，而且所用的脱甲基试剂氢滨酸的价格远低于氢碘酸。
最后，通过对染料木素、大豆黄素、5，7一二轻基异黄酮、5一轻基一4‘，7一二甲氧
基异黄酮、4，，5一二轻基一7一甲氧基异黄酮、4护一轻基一7一甲氧基异黄酮、5一轻基一7一甲
氧基异黄酮的IHNMR谱图的对照分析，研究得到了4’，5，7一三甲氧基异黄酮的脱
甲基顺序。
在第二部分，以苯胺和3一氯丙酞氯为原料，经酞化、环化、硝化、还原和重
氮化水解反应制得了3，4一二氢一2(IH)喳琳酮衍生物，提出了一条合成6一轻基一3，4-
二氢一2(1H)哇琳酮的新工艺路线，总收率可达65%以上。一方面，文献中报道的
6一氨基一3，4一二氢一2(1H)喳琳酮的总收率(以苯胺计)为58.6%，而新工艺路线的
总收率(以苯胺计)可提高到78%，高于文献中报道的收率。另一方面，在合成
3，4一二氢一2(1H)哇琳酮二取代衍生物的反应中，得到了一个新化合物，即6一氨基
一8一硝基一3，4一二氢一2(IH)喳琳酮(经检索，无相关报道)。值得一提的是，在硝
基还原为氨基的反应中，还原产物6一氨基一8一硝基一3，4一二氢一2(1H)喳琳酮的收率可
达92.2%，6一氨基一3，4-二氢一2(IH)哇琳酮和6，8一二氨基一3，4一二氢一2(IH)哇琳
酮的收率分别达到99.6%和99.5%。
从总体上讲，本文设计的异黄酮类化合物及3，4一二氢·2(1H)喳琳酮衍生物的
合成路线，具有原料价廉，路线简单，操作简便，反应条件温和，无需高温、高
压、惰性气体保护等苛刻的反应条件等优点，且无繁杂的后处理过程，同现有的
其它合成路线相比，更适于工业化大规模生产。
This dissertation studies on new methods of synthesis isoflavonoids and 3,4-dihydro-2(lH)quinolinone derivatives with higher yield and simpler operation. It covers nine chapters which can be divided into two parts.
The first part which contains six chapters gives the comments on the synthesis of isoflavonoids. This part not only designs and synthesizes genistein, daidzein, 5,7-dihydroxyisoflavone, 6-bromo-4',7-dimethoxyisoflavone and their derivatives, but also discusses the technical conditions.
Firstly, we replace expensive material l,3,5-trihydroxybenzene(produced from TNT, whose price is about 600,000 yuan/t) with cheap material 1,3,5-trimethoxybenzene (160,000 yuan/t) and get 4',5,7-trihydroxyisofiavone or 5,7-dihydroxyisoflavone by demethylation reaction of 4',5,7-trimethoxyisoflavone or 5,7-dimethoxyisoflavone which can be gotten via cyclizing of phenyl benzyl ketone. This way not only costs less but also yields higher, the total yield can reach 60-75%. Secondly, two new compounds are found in this part: 2-hydroxy-4,4'-dimethoxy-5-bromodeoxy-benzoin and 6-bromo-4',7-dimethoxy-isoflavone. They are prepared in synthesis of 6-bromo-4',7-dimethoxyisoflavone. Then, the part puts forward the system of demethylation reaction which is hydrobromic acid(2000~5200yuan/t) or hydrobromic acid/PTC for the first time, and it is much cheaper than hydroiodic acid(l 80000 ~200000yuan/t), the common demethyl reagent in references. We use this method to take off all the methyl and get genistein, daidzein and 5,7-
dihydroxyisoflavone in one time. At last, we investigate the order and mechanism of the demethylation of 4',5,7-dimethoxyisoflavone, and testify them by 'HNMR spectrum of genistein, daidzein, 5,7-dihydroxyisoflavone, 5-hydroxy-4',7-dimethoxyisoflavone, 4',5-dihydroxy-7-methoxyisoflavone, 4'-hydr-oxy-7-methoxyisoflavone and 5-hydroxy-7-methoxyisoflavone.
ABSTRACT
The second part, which contains two chapters, designs and synthesizes 3,4-dihydro-2(lH)quinolinone derivatives. In this part, a new mehod of synthesis 6-hydroxy-3,4-dihydro-2(lH)quinolinone is brought forward, and the total yield gets upwards of 65%. On the one hand, the total yield of 6-amino-3,4-dihydro-2(lH)quinolinone can reach 78% (from aniline), which is more than 58.6% total yield(from aniline) that mentioned in references. On the other hand, we get a new compound in the reaction of synthesis 3,4-dihydro-2(lH)quinolinone derivatives, which is 6-amhio-8-nitro-3,4-dihydro-2(lH)quinolinone. Furthermore, the yields of reduction are very high, those of 6-amino-3,4-dihydro-2(lH)quinolinone and 6,8-diamino-3,4-dihydro- 2(lH)quinolinone are basically quantitation.
Generally speaking, the methods of synthesis isoflavonoids and 3,4-dihydro-2(lH)quinolinone derivatives in this paper cost less, operate simpler, yield higher and postprocess easier with gentle reaction condition. They are fit for mass production compared with other current ways.
本论文包括两个部分，第一部分研究了异黄酮类化合物的合成新方法，第二部分研究了3，4-二氢-2(1H)喹啉酮衍生物的合成新方法。
在第一部分，综述了异黄酮化合物的合成方法，在此基础上，自行设计了合成路线，经赫氏(Hoesch)或酰化反应、脱甲基化、环化和脱甲基化反应合成了染料木素及其衍生物、大豆黄素及其衍生物、5，7-二羟基异黄酮及其衍生物以及6-溴-4′，7-二甲氧基异黄酮，就工艺条件进行了探讨，得到了最佳反应条件。
文献报道的染料木素及5，7-二羟基异黄酮的合成反应中，一般采用1，3，5-三羟基苯为原料，总收率在45-50％左右。首先，本文中在原料的选择上，以价格低廉且供应充足的1，3，5-三甲氧基苯为原料，经苯基苄基酮路线环合得到4′，5，7-三甲氧基异黄酮或5，7-二甲氧基异黄酮后，直接以氢溴酸／相转移催化剂或氢溴酸为脱甲基反应体系，一次性脱去全部甲基，得到染料木素或5，7-二羟基异黄酮，采用新工艺路线后，不仅降低了成本，且可将总收率提高到60-75％，还可以通过对脱甲基试剂的调整及反应条件的控制，得到4′，5，7-三甲氧基异黄酮和5，7-二甲氧基异黄酮的部分脱甲基产物。
其次，在合成6-溴-4′，7-二甲氧基异黄酮的过程中得到了新化合物2-羟基-4，4′-二甲氧基-5-溴脱氧安息香和6-溴-4′，7-二甲氧基异黄酮(经检索，无相关报道)，发现了在6-溴-4′，7-二甲氧基异黄酮在脱甲基过程中存在脱溴现象，并从机理上进行了分析。
再次，根据文献报道，脱甲基试剂中只有氢碘酸可一次性脱去全部甲基，而本文中采用氢溴酸／相转移催化剂(四正丁基溴化铵、苄基三乙基氯化铵或三甲基十六烷基溴化铵等)或氢溴酸为脱甲基反应体系，一次性脱去全部甲基，直接
浙江大学博士学位论文
摘要
得到染料木素、大豆黄素和5，7一二轻基异黄酮，具有首创性，不仅可以脱去全部
甲基，而且所用的脱甲基试剂氢滨酸的价格远低于氢碘酸。
最后，通过对染料木素、大豆黄素、5，7一二轻基异黄酮、5一轻基一4‘，7一二甲氧
基异黄酮、4，，5一二轻基一7一甲氧基异黄酮、4护一轻基一7一甲氧基异黄酮、5一轻基一7一甲
氧基异黄酮的IHNMR谱图的对照分析，研究得到了4’，5，7一三甲氧基异黄酮的脱
甲基顺序。
在第二部分，以苯胺和3一氯丙酞氯为原料，经酞化、环化、硝化、还原和重
氮化水解反应制得了3，4一二氢一2(IH)喳琳酮衍生物，提出了一条合成6一轻基一3，4-
二氢一2(1H)哇琳酮的新工艺路线，总收率可达65%以上。一方面，文献中报道的
6一氨基一3，4一二氢一2(1H)喳琳酮的总收率(以苯胺计)为58.6%，而新工艺路线的
总收率(以苯胺计)可提高到78%，高于文献中报道的收率。另一方面，在合成
3，4一二氢一2(1H)哇琳酮二取代衍生物的反应中，得到了一个新化合物，即6一氨基
一8一硝基一3，4一二氢一2(IH)喳琳酮(经检索，无相关报道)。值得一提的是，在硝
基还原为氨基的反应中，还原产物6一氨基一8一硝基一3，4一二氢一2(1H)喳琳酮的收率可
达92.2%，6一氨基一3，4-二氢一2(IH)哇琳酮和6，8一二氨基一3，4一二氢一2(IH)哇琳
酮的收率分别达到99.6%和99.5%。
从总体上讲，本文设计的异黄酮类化合物及3，4一二氢·2(1H)喳琳酮衍生物的
合成路线，具有原料价廉，路线简单，操作简便，反应条件温和，无需高温、高
压、惰性气体保护等苛刻的反应条件等优点，且无繁杂的后处理过程，同现有的
其它合成路线相比，更适于工业化大规模生产。
This dissertation studies on new methods of synthesis isoflavonoids and 3,4-dihydro-2(lH)quinolinone derivatives with higher yield and simpler operation. It covers nine chapters which can be divided into two parts.
The first part which contains six chapters gives the comments on the synthesis of isoflavonoids. This part not only designs and synthesizes genistein, daidzein, 5,7-dihydroxyisoflavone, 6-bromo-4',7-dimethoxyisoflavone and their derivatives, but also discusses the technical conditions.
Firstly, we replace expensive material l,3,5-trihydroxybenzene(produced from TNT, whose price is about 600,000 yuan/t) with cheap material 1,3,5-trimethoxybenzene (160,000 yuan/t) and get 4',5,7-trihydroxyisofiavone or 5,7-dihydroxyisoflavone by demethylation reaction of 4',5,7-trimethoxyisoflavone or 5,7-dimethoxyisoflavone which can be gotten via cyclizing of phenyl benzyl ketone. This way not only costs less but also yields higher, the total yield can reach 60-75%. Secondly, two new compounds are found in this part: 2-hydroxy-4,4'-dimethoxy-5-bromodeoxy-benzoin and 6-bromo-4',7-dimethoxy-isoflavone. They are prepared in synthesis of 6-bromo-4',7-dimethoxyisoflavone. Then, the part puts forward the system of demethylation reaction which is hydrobromic acid(2000~5200yuan/t) or hydrobromic acid/PTC for the first time, and it is much cheaper than hydroiodic acid(l 80000 ~200000yuan/t), the common demethyl reagent in references. We use this method to take off all the methyl and get genistein, daidzein and 5,7-
dihydroxyisoflavone in one time. At last, we investigate the order and mechanism of the demethylation of 4',5,7-dimethoxyisoflavone, and testify them by 'HNMR spectrum of genistein, daidzein, 5,7-dihydroxyisoflavone, 5-hydroxy-4',7-dimethoxyisoflavone, 4',5-dihydroxy-7-methoxyisoflavone, 4'-hydr-oxy-7-methoxyisoflavone and 5-hydroxy-7-methoxyisoflavone.
ABSTRACT
The second part, which contains two chapters, designs and synthesizes 3,4-dihydro-2(lH)quinolinone derivatives. In this part, a new mehod of synthesis 6-hydroxy-3,4-dihydro-2(lH)quinolinone is brought forward, and the total yield gets upwards of 65%. On the one hand, the total yield of 6-amino-3,4-dihydro-2(lH)quinolinone can reach 78% (from aniline), which is more than 58.6% total yield(from aniline) that mentioned in references. On the other hand, we get a new compound in the reaction of synthesis 3,4-dihydro-2(lH)quinolinone derivatives, which is 6-amhio-8-nitro-3,4-dihydro-2(lH)quinolinone. Furthermore, the yields of reduction are very high, those of 6-amino-3,4-dihydro-2(lH)quinolinone and 6,8-diamino-3,4-dihydro- 2(lH)quinolinone are basically quantitation.
Generally speaking, the methods of synthesis isoflavonoids and 3,4-dihydro-2(lH)quinolinone derivatives in this paper cost less, operate simpler, yield higher and postprocess easier with gentle reaction condition. They are fit for mass production compared with other current ways.
引文
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