中文摘要
 

由于α-氨基膦酸酯衍生物在結(jié)構(gòu)上近似于天然氨基酸, 而且這種化合物有著極大的作用和優(yōu)點(diǎn)。α-氨基膦酸酯衍生物繼承了類似于天然氨基酸的好的生物利用性能，毒性低且殘留量低，所以其一般被用作殺蟲劑、除草劑、殺菌劑、生長調(diào)節(jié)劑、酶的抑制劑等，甚至還可用作抗癌藥物和抗病毒藥物。因此高效的α-氨基膦酸酯衍生物合成方法一直備受關(guān)注。

α-氨基膦酸酯衍生物在現(xiàn)在利用極為廣泛，且合成方法也很多。高效的合成方法的探究十分重要，而現(xiàn)階段許多合成方法是通過使用有機(jī)溶劑的兩步合成法，這種方法一般由于有機(jī)溶劑的使用而存在最終產(chǎn)物難提取、產(chǎn)率低和對(duì)環(huán)境不好的弊端。在這種情況下，本文提出了新的無溶劑的“一鍋法”合成法來合成產(chǎn)物。本文詳細(xì)的介紹了利用三甲基氯硅烷（TMSCl）在無溶劑的條件下合成一系列的α-氨基膦酸酯衍生物。具體是：
在無溶劑條件下，利用取代苯甲醛、取代苯胺和亞磷酸二乙酯為原料，并以TMSCl作為催化劑，“一鍋法”合成了一系列的α-氨基膦酸酯衍生物。此外，還研究分析了原料的配比和TMSC1的濃度對(duì)合成產(chǎn)物和產(chǎn)物濃度的影響。最后，其結(jié)構(gòu)經(jīng)1H NMR和代表化合物的X-單晶衍射進(jìn)行了表征。此合成方法反應(yīng)條件溫和、操作方便、產(chǎn)率較高且對(duì)環(huán)境友好，是一種綠色的合成方法。

Abstract

As the stucture of α-amino phosphonate derivatives is similar to natural amino acids, this compound play an important role in the field of biology and pharmacology. α-amino phosphonate derivative inherited the good bioavailability properties from the natural amino acid, it shows low toxicity and low residual amount, generally, it is used as insecticides, herbicides , fungicides , growth-regulating agents, enzymes inhibitors , and even can be used as anti-cancer drugs and antiviral drugs. So theα-amino phosphonate derivatives have attracted much attention, and an efficient synthetic method of α-amino phosphonate derivatives is very important.

Nowadays, α-amino phosphonate derivatives are applied widely, and there are lots of synthesis methods of α-amino phosphonate derivatives. The efficient systhesis method ofα-amino phosphonate derivatives is very important, and the most famous  synthetic method is two-step synthesis method, which use an organic solvent method. But this method have some disadvantages, such as the final product extraction is difficult, low yield and some environmental issues. In this case, this paper proposed a “one-pot” synthesis method to synthesize a new solvent-free product. This paper describes a new method that use trimethylchlorosilane (TMSCl) as synthesis catalyst for solvent-free synethsis, the product is a series ofα-amino phosphonate derivatives.
Specifically, in the solvent-free react system, the use of substituted benzaldehyde, substituted aniline and diethyl phosphite as raw materials, and TMSCl as a catalyst, the "one-pot" synthesis method has been used to synthesized a series of α-amino phosphonate derivatives. Furthermore, this paper also analysed the effect of TMSC1 concentration and the ratio of raw materials for the yield of synthetic products. Finally, the structure of representative compoud were tested by X-single-crystal and 1H NMR. It is indicated that this synthesis method is a gree synthetic method with mild reaction conditions, the convenient way of operation, high yields and environmental friendly.

目  錄

中文摘要 I
Abstract II
第一章  緒論 1
1.1 α-氨基膦酸酯衍生物的應(yīng)用 1
1.1.1α-氨基膦酸酯衍生物用作除草劑 1
1.1.2α-氨基膦酸酯衍生物的抗菌作用 3
1.1.3α-氨基膦酸酯衍生物用作植物生長素 4
1.1.4α-氨基膦酸酯衍生物的酶抑制劑和抗病毒作用 5
1.1.5α-氨基膦酸酯衍生物的抗癌作用 7
1.1.6 N端決定α-氨基膦酸酯衍生物的應(yīng)用 7
1.2 α-氨基膦酸酯衍生物的合成進(jìn)展 8
1.2.1 無溶劑合成法制備α-氨基膦酸酯衍生物 9
1.2.2 微波合成法制備α-氨基膦酸酯衍生物 11
1.2.3 “一鍋法”合成法制備α-氨基膦酸酯衍生物 13
1.2.4 離子液體在無溶劑條件下催化合成α-氨基膦酸酯衍生物 15
1.3 α-氨基膦酸酯衍生物的合成中的影響因素 16
1.3.1 反應(yīng)中的投料比的影響 17
1.3.2 反應(yīng)溫度的影響 17
1.3.3 催化劑對(duì)反應(yīng)的影響 18
1.4 目標(biāo)化合物合成的設(shè)計(jì)和研究意義 19
1.4.1 目標(biāo)化合物合成的思路 19
1.4.2 目標(biāo)化合物的合成路線 20
1.4.3 本課題的研究意義 21
第二章  實(shí)驗(yàn)部分 22
2.1 實(shí)驗(yàn)儀器與試劑 22
2.1.1 實(shí)驗(yàn)試劑 22
2.1.2 實(shí)驗(yàn)儀器 22
2.2 α-氨基膦酸酯衍生物的合成 23
2.2.1 試劑處理 23
2.2.2 α-氨基膦酸酯衍生物的合成步驟 23
2.2.3 α-氨基膦酸酯衍生物的提純處理 24
2.2 α-氨基膦酸酯衍生物的反應(yīng)條件優(yōu)化實(shí)驗(yàn) 24
2.3 α-氨基膦酸酯衍生物產(chǎn)物的分析 25
2.3.1 α-氨基膦酸酯衍生物產(chǎn)物的1H NMR分析 25
2.3.2 α-氨基膦酸酯衍生物產(chǎn)物的13C NMR分析 25
2.3.3 α-氨基膦酸酯衍生物產(chǎn)物的元素分析 26
2.3.3 α-氨基膦酸酯衍生物產(chǎn)物的X單晶衍射 26
第三章  實(shí)驗(yàn)結(jié)果與討論 28
3.1 α-氨基膦酸酯衍生物的合成結(jié)果與分析 28
3.2催化劑TMSC1的用量對(duì)α-氨基膦酸酯衍生物產(chǎn)率的影響 29
3.3α-氨基膦酸酯衍生物產(chǎn)物的1H NMR結(jié)果與分析 30
3.4α-氨基膦酸酯衍生物產(chǎn)物的13C NMR結(jié)果與分析 34
3.5α-氨基膦酸酯衍生物產(chǎn)物的元素分析結(jié)果 37
3.6α-氨基膦酸酯衍生物產(chǎn)物的單晶衍射結(jié)果與分析 37
第四章  結(jié)論 39
參考文獻(xiàn) 40
附圖 部分化合物的圖譜 44
在學(xué)期間發(fā)表的文章 45
致    謝 46

第一章  緒論

1.1 α-氨基膦酸酯衍生物的應(yīng)用

目前，有機(jī)磷化學(xué)這門學(xué)科已經(jīng)發(fā)展成獨(dú)立的學(xué)科，而且有機(jī)磷化學(xué)在整個(gè)化學(xué)的研究領(lǐng)域中都占據(jù)著極為重要的地位。大部分的其他學(xué)科也會(huì)在發(fā)展中會(huì)涉及到這一學(xué)科。20世紀(jì)30年代，一些學(xué)者偶然的情況下發(fā)現(xiàn)了有機(jī)磷毒劑和有機(jī)磷殺蟲劑后，標(biāo)志著整個(gè)有機(jī)磷化學(xué)正式開始發(fā)展，并且逐步走向成熟，同時(shí)也開創(chuàng)了整個(gè)新的農(nóng)藥工業(yè)。
α-氨基膦酸酯衍生物是和天然氨基酸有著類似結(jié)構(gòu)的化合物，同時(shí)它也是有機(jī)磷化學(xué)在近幾十年來發(fā)展起來重要的組成部分。1959年，， Horiguhci和knadastu兩位科學(xué)家從綿羊體內(nèi)分離出來α-氨基膦酸至今已經(jīng)有50多年的歷史了。α-氨基膦酸酯是α-氨基酸和擬肽水解中間產(chǎn)物的結(jié)構(gòu)類似物，具有一定的生物活性。正是基于這一點(diǎn)，近些年來，α-氨基膦酸酯衍生物的生物活性研究受到了許多科學(xué)家的廣泛關(guān)注，其結(jié)構(gòu)的多樣性同時(shí)也為相關(guān)新的衍生物的合成奠定了基礎(chǔ)。研究表明，不同的α-氨基膦酸酯衍生物具有不同的生物活性。迄今為止，研究者已經(jīng)發(fā)現(xiàn)了α-氨基膦酸酯衍生物具有抗植物病毒[1]、除草[2]、植物生長調(diào)節(jié)[3]、殺菌[4]、酶抑制劑活性[5]、抗癌[6]、抗氧化能力[7, 8]等生物活性。此外研究還發(fā)現(xiàn)它在動(dòng)物體內(nèi)有著一定的抗血栓和抗動(dòng)脈粥樣硬化的重要生物活性[9-13]。
因此，α-氨基膦酸酯衍生物備受科學(xué)家的關(guān)注，許多新的α-氨基膦酸酯衍生物通過不同的方法合成出來，同時(shí)不同的生物活性也在被不斷地發(fā)現(xiàn)，它在各個(gè)領(lǐng)域的應(yīng)用方面的研究也逐漸成熟起來[14]。

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