含硅有机锡化合物的合成、结构、生物活性和催化活性研究
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摘要
具有杀菌、杀螨、抗癌及催化活性的各种有机锡化合物的研究越来越为人们所关注。然而,有机锡化合物的毒副作用在一定程度上限制了它们的实际应用。寻求具有应用前景、高效低毒的有机锡化合物是目前有机锡化学研究的重要课题之一。
为探讨在有机锡化合物分子中引入硅原子后,烃基结构的变化对有机锡化合物的物化性质、生物活性和催化活性的影响,本论文对一系列含硅有机锡化合物进行了研究。
1、设计、合成了以下六类新的含硅烃基锡化合物:
(1)含硅混合二烃基锡二卤化物R(R'Me_2SiCH_2)SnX_2 (R=Ph,Cy,Bu;X=Cl,Br;R'=Me,Et)
(2)含硅混合二烃基锡二芳香酸酯Cy(Me_3SiCH_2)Sn(OCOAr)_2 (Ar=C_6H_4-H,C_6H_4-F-p,C_6H_4-Cl-p,C_6H_4-Br-p,C_6H_4-NO_2-p,C_6H_4-OCH_3-p, C_6H_4-CH_3-p,C_6H_4-NO_2-m,C_6H_4-NH_2-o)
(3)含硅混合二烃基锡二卤化物-邻菲咯啉配合物R(R'Me_2SiCH_2)SnCl_2(Phen) (R=Ph,Cy;R'=Me,Et)
(4)含硅混合三烃基锡溴化物(Me_3SiCH_2)Bu_2SnBr
(5)含硅混合三烃基锡芳香酸酯(Me_3SiCH_2)Bu_2SnOCOAr (Ar=C_6H_5,C_6H_4-F-p,C_6H_4-Cl-p,C_6H_4-Cl-m,C_6H_4-Br-p,C_6H_4-NO_2-p,C_6H_4-OCH_3-p,C_6H_4-CH_3-p,C_6H_4-NO_2-m)
(6)含硅四烃基二锡氧烷[ClBu_2SnOSn(CH_2SiMe_3)_2Cl]_2和[p-NO_2C_6H_4CO_2)Bu_2Sn-OSn(CH_2SiMe_3)_2(O_2CC_6H_4NO_2-p)]2
并对一些含硅有机锡化合物的合成方法和反应条件进行了初步探讨。
2、通过IR、~1HNMR、~(13)C NMR和MS的测定,确定了这些化合物的分子结构。结构分析的结果表明,环己基-[(三甲基硅基)甲基]锡二芳香酸酯的羰基氧原子可能与锡原子发生了配位,形成以锡原子为中心的六配位扭曲八面体构型。含硅混合二烃基锡二卤化物-邻菲咯啉配合物的锡原子也可能是六配位的。而二丁基-[(三甲基硅基)甲基]锡羧酸酯则可能形成了中心锡原子为四配位的单体结构。
3、初步测定了其中部分羧酸酯化合物的生物活性。初步结果显示,有机锡化合物在引入硅原子、改变烃基结构后,仍保留有一定的生物活性。
(1)二丁基-[(三甲基硅基)甲基]锡羧酸酯具有较好的杀螨活性和一定的杀菌活性。
(2)环己基-[(三甲基硅基)甲基]锡二芳香酸酯具有较强的体外抗肿瘤活性,且比含硅单一二烃基锡芳香酸酯更好。
4、通过对含硅三烃基锡氯化物、含硅三烃基锡氧化物、含硅二烃基锡氯化物、含硅二烃基锡二芳香羧酸酯及含硅四烃基二锡氧烷等几类含硅有机锡化合物在酯化和缩醛反应中的催化活性的初步研究,结果显示有机锡化合物在引入硅原子后仍具有较好的催化活性。
本文对一系列新的含硅有机锡化合物的初步研究,丰富了有机锡化学的内容,为研究开发安全高效的有机锡农药、有机锡药物和有机锡催化剂作了一些初步探索工作。
There has been growing interest in the study of a variety of organotin compounds with fungicidal, acaricidal, antitumour and catalytic activities. However, organotin compounds are limited to certain extent in practical application due to their toxicity. To discover safe and efficient organotin compounds with application prospect becomes one of the important subjects of investigation in organotin chemistry.
The studies on a series of organotin compounds containing silicon were carried out to evaluate the influence on the physical-chemical property, biological activity and catalytic activity of the organotin compounds, after the introduction of silicon atom as well as variation of alkyl group.
1. Six types of new organotin compounds containing silicon were designed and synthesized as follows:
(1) Mixed diorganotin halides R(R'Me_2SiCH2)SnX_2
(2) Mixed diorganotin arylcarboxylates Cy(Me_3SiCH_2)Sn(OCOAr)_2
(3) Mixed diorganotin chloride-phenanthroline complexes
(4) Mixed triorganotin bromide (Me_3SiCH_2)Bu_2SnBr
(5) Mixed triorganotin arylcarboxylates (Me_3SiCH_2)Bu_2SnOCOAr
(6) Tetraorganodistannoxanes [ClBu_2SnOSn(CH_2SiMe_3)_2Cl]_2 and [(p-NO_2C_6H_4CO_2) -Bu_2SnOSn(CH_2SiMe_3)_2(O_2CC_6H_4NO_2-p)]_2。
The synthetic methods and reaction conditions of some organotin compounds containing silicon were also discussed.
2. The molecular structures of these new compounds were characterized by IR,~1H NMR, ~(13)C NMR and MS. The result showed that in the molecule of cyclohexyl(trimethylsilylmethyl)tin arylcarboxylates, the carbonyl oxygen atom was probably coordinated to certain extent with tin atom giving a six-coordinated distorted octahedral geometry. In mixed diorganotin halide-phenanthroline complexes containing silicon, the tin atom was possibly six-coordinated. In dibutyl(trimethylsilylmethyl)tin arylcarboxylates, the central tin atom was probably four-coordinated affording a monomeric structure.
3. The biological activities of some carboxylates were determined preliminarily. The result showed that the organotin compounds still remained certain biological activities after the introduction of silicon atom as well as variation of alkyl groups.
(1) The dibutyl(trimethylsilylmethyl)tin arylcarboxylates not only displayed a good acaricidal activity, but also showed certain fungicidal activity.
(2) The cyclohexyl(trimethylsilylmethyl)tin arylcarboxylates had a good antitumour activity in vitro, which was superior to that of simple diorganotin carboxylates containing silicon.
4. The preliminarily study of catalytic activity in esterification and acetalization, of some organotin compounds containing silicon such as triorganotin chlorides, triorganotin oxide, diorganotin chlorides, diorganotin arylcarboxylates and tetraorganodistannoxanes, were carried out. The result showed that organotin compounds still had certain catalytic activity after the introduction of silicon atom.This preliminary study on a series of new organotin compounds containing silicon may enrich the resources of organotin chemistry, and provide a basis for the exploitation of safe and efficient organotin antitumour drugs, organotin biocides and organotin catalysts.
为探讨在有机锡化合物分子中引入硅原子后,烃基结构的变化对有机锡化合物的物化性质、生物活性和催化活性的影响,本论文对一系列含硅有机锡化合物进行了研究。
1、设计、合成了以下六类新的含硅烃基锡化合物:
(1)含硅混合二烃基锡二卤化物R(R'Me_2SiCH_2)SnX_2 (R=Ph,Cy,Bu;X=Cl,Br;R'=Me,Et)
(2)含硅混合二烃基锡二芳香酸酯Cy(Me_3SiCH_2)Sn(OCOAr)_2 (Ar=C_6H_4-H,C_6H_4-F-p,C_6H_4-Cl-p,C_6H_4-Br-p,C_6H_4-NO_2-p,C_6H_4-OCH_3-p, C_6H_4-CH_3-p,C_6H_4-NO_2-m,C_6H_4-NH_2-o)
(3)含硅混合二烃基锡二卤化物-邻菲咯啉配合物R(R'Me_2SiCH_2)SnCl_2(Phen) (R=Ph,Cy;R'=Me,Et)
(4)含硅混合三烃基锡溴化物(Me_3SiCH_2)Bu_2SnBr
(5)含硅混合三烃基锡芳香酸酯(Me_3SiCH_2)Bu_2SnOCOAr (Ar=C_6H_5,C_6H_4-F-p,C_6H_4-Cl-p,C_6H_4-Cl-m,C_6H_4-Br-p,C_6H_4-NO_2-p,C_6H_4-OCH_3-p,C_6H_4-CH_3-p,C_6H_4-NO_2-m)
(6)含硅四烃基二锡氧烷[ClBu_2SnOSn(CH_2SiMe_3)_2Cl]_2和[p-NO_2C_6H_4CO_2)Bu_2Sn-OSn(CH_2SiMe_3)_2(O_2CC_6H_4NO_2-p)]2
并对一些含硅有机锡化合物的合成方法和反应条件进行了初步探讨。
2、通过IR、~1HNMR、~(13)C NMR和MS的测定,确定了这些化合物的分子结构。结构分析的结果表明,环己基-[(三甲基硅基)甲基]锡二芳香酸酯的羰基氧原子可能与锡原子发生了配位,形成以锡原子为中心的六配位扭曲八面体构型。含硅混合二烃基锡二卤化物-邻菲咯啉配合物的锡原子也可能是六配位的。而二丁基-[(三甲基硅基)甲基]锡羧酸酯则可能形成了中心锡原子为四配位的单体结构。
3、初步测定了其中部分羧酸酯化合物的生物活性。初步结果显示,有机锡化合物在引入硅原子、改变烃基结构后,仍保留有一定的生物活性。
(1)二丁基-[(三甲基硅基)甲基]锡羧酸酯具有较好的杀螨活性和一定的杀菌活性。
(2)环己基-[(三甲基硅基)甲基]锡二芳香酸酯具有较强的体外抗肿瘤活性,且比含硅单一二烃基锡芳香酸酯更好。
4、通过对含硅三烃基锡氯化物、含硅三烃基锡氧化物、含硅二烃基锡氯化物、含硅二烃基锡二芳香羧酸酯及含硅四烃基二锡氧烷等几类含硅有机锡化合物在酯化和缩醛反应中的催化活性的初步研究,结果显示有机锡化合物在引入硅原子后仍具有较好的催化活性。
本文对一系列新的含硅有机锡化合物的初步研究,丰富了有机锡化学的内容,为研究开发安全高效的有机锡农药、有机锡药物和有机锡催化剂作了一些初步探索工作。
There has been growing interest in the study of a variety of organotin compounds with fungicidal, acaricidal, antitumour and catalytic activities. However, organotin compounds are limited to certain extent in practical application due to their toxicity. To discover safe and efficient organotin compounds with application prospect becomes one of the important subjects of investigation in organotin chemistry.
The studies on a series of organotin compounds containing silicon were carried out to evaluate the influence on the physical-chemical property, biological activity and catalytic activity of the organotin compounds, after the introduction of silicon atom as well as variation of alkyl group.
1. Six types of new organotin compounds containing silicon were designed and synthesized as follows:
(1) Mixed diorganotin halides R(R'Me_2SiCH2)SnX_2
(2) Mixed diorganotin arylcarboxylates Cy(Me_3SiCH_2)Sn(OCOAr)_2
(3) Mixed diorganotin chloride-phenanthroline complexes
(4) Mixed triorganotin bromide (Me_3SiCH_2)Bu_2SnBr
(5) Mixed triorganotin arylcarboxylates (Me_3SiCH_2)Bu_2SnOCOAr
(6) Tetraorganodistannoxanes [ClBu_2SnOSn(CH_2SiMe_3)_2Cl]_2 and [(p-NO_2C_6H_4CO_2) -Bu_2SnOSn(CH_2SiMe_3)_2(O_2CC_6H_4NO_2-p)]_2。
The synthetic methods and reaction conditions of some organotin compounds containing silicon were also discussed.
2. The molecular structures of these new compounds were characterized by IR,~1H NMR, ~(13)C NMR and MS. The result showed that in the molecule of cyclohexyl(trimethylsilylmethyl)tin arylcarboxylates, the carbonyl oxygen atom was probably coordinated to certain extent with tin atom giving a six-coordinated distorted octahedral geometry. In mixed diorganotin halide-phenanthroline complexes containing silicon, the tin atom was possibly six-coordinated. In dibutyl(trimethylsilylmethyl)tin arylcarboxylates, the central tin atom was probably four-coordinated affording a monomeric structure.
3. The biological activities of some carboxylates were determined preliminarily. The result showed that the organotin compounds still remained certain biological activities after the introduction of silicon atom as well as variation of alkyl groups.
(1) The dibutyl(trimethylsilylmethyl)tin arylcarboxylates not only displayed a good acaricidal activity, but also showed certain fungicidal activity.
(2) The cyclohexyl(trimethylsilylmethyl)tin arylcarboxylates had a good antitumour activity in vitro, which was superior to that of simple diorganotin carboxylates containing silicon.
4. The preliminarily study of catalytic activity in esterification and acetalization, of some organotin compounds containing silicon such as triorganotin chlorides, triorganotin oxide, diorganotin chlorides, diorganotin arylcarboxylates and tetraorganodistannoxanes, were carried out. The result showed that organotin compounds still had certain catalytic activity after the introduction of silicon atom.This preliminary study on a series of new organotin compounds containing silicon may enrich the resources of organotin chemistry, and provide a basis for the exploitation of safe and efficient organotin antitumour drugs, organotin biocides and organotin catalysts.
引文
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