N-<(trimethoxysilyl)methyl>-N-methylacetamide | 149219-02-3

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: N-<(trimethoxysilyl)methyl>-N-methylacetamide
• 英文别名: N-(trimethoxysilylmethyl)-N-methylacetamide；N-methyl-N-(trimethoxysilylmethyl)acetamide；N-[(trimethoxysilyl)methyl]-N-methylacetamide
• CAS: 149219-02-3
• 化学式: C₇H₁₇NO₄Si
• 分子量: 207.302
• InChiKey: LDTKKHAKHFHXAJ-UHFFFAOYSA-N

物化性质

• 沸点：
  206.0±23.0 °C(predicted)
• 密度：
  1.019±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.12
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-<(trimethoxysilyl)methyl>-N-methylacetamide 在 三氟化硼乙醚 作用下， 以 正己烷 为溶剂， 反应 0.5h， 以92%的产率得到N-(trifluorosilylmethyl)-N-methylacetamide
  参考文献：
  名称：

  Synthesis, structure and dynamic stereochemistry of (O→Si)-chelate N-(trifluorosilylmethyl)-[N-(S)-(1-phenylethyl)]acetamide and 1-(trifluorosilylmethyl)-2-oxoperhydroazepine: Retention of the O→Si coordination in the adduct with KF and 18-crown-6

  摘要：

  The novel compounds, N-(trifluorosilylmethyl)-[N-(S)-(1-phenylethyl)]- acetamide (1a) and 1-(trifluorosilylmethyl)- 2-oxoperhydroazepine (1b) have been prepared from the corresponding NH-compounds using ClCH2SiCl3/Et3N or ClCH2SiCl3/(Me3Si)(2)NH followed by methanolysis or hydrolysis of the reaction mixture in the presence of Lewis bases, and then BF3 etherate. Potassium-(18-crown-6)-(2-oxoperhydroazepinomethyl) tetrafluorosilicate (2) was synthesized by reaction of the trifluoride (1b) with KF in the presence of 18-crown-6. Using F-19, Si-29 NMR and X-ray diffraction techniques it was established that the silicon atom is pentacoordinate in the trifluorides (1a, b) and hexacoordinate in the adduct 2. Thus the internal coordination of the O --> Si bond present in the trifluoride (1b) is retained in the adduct 2. The stereochemical non-rigidity of the trifluorides (1a, b) and the N-(trifluorosilylmethyl)-N-methylacetamide (1c) was investigated using dynamic F-19 NMR spectroscopy. The activation barriers for permutational isomerization are in the range 9.5-10 kcal mol(-1). Lower values of Delta G(#) for permutation of trifluorides (1a-c) compared to the monofluorides with the coordination core OSiC3F together with small negative values for the activation entropy implies a non-dissociative mechanism. Quantum-chemical analysis suggests a mechanism involving a turnstile rotation. (C) 2008 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2008.01.033
• 作为产物：
  描述：

  一氯甲基三甲氧基硅烷 、 N-甲基-N-(三甲基硅基)乙酰胺 在 N,N-二乙基苯胺 作用下， 反应 0.5h， 以17%的产率得到N-<(trimethoxysilyl)methyl>-N-methylacetamide
  参考文献：
  名称：

  Kramarova, V.P.; Shipov, A.G.; Baukov, Yu.I., Journal of general chemistry of the USSR, 1992, vol. 62, # 11.2, p. 2113 - 2119

  摘要：

  DOI：

文献信息

• Synthesis and specific features of the structure of the mixed anionic six-coordinate silicon complexes with the (O,O)-dianionic and (C,O)-monoanionic chelate ligands
  作者：A. A. Korlyukov、A. G. Shipov、E. P. Kramarova、Vad. V. Negrebetskii、Yu. I. Baukov

  DOI：10.1007/s11172-008-0284-4

  日期：2008.10

  Dicyclohexylammonium salts of bis(1,2-catecholato-O,O′)-[(N-methylacetamido)methyl-C,O]silicate and bis(1,2-catecholato-O,O′)-[(2-oxohexahydroazepin-1-yl)methyl-C,O]silicate were synthesized by the transesterification of the corresponding trimethoxysilyl derivatives by pyrocatechol in the presence of dicyclohexylamine. According to the X-ray diffraction data, the synthesized salts are the anionic silicon complexes, in which the Si atoms are six-coordinate due to two (O,O′)-dianionic and one (C,O)-monoanionic chelate ligands. In the latter, chelating occurs due to the formation of the intramolecular (intraionic) coordination bond O→Si.

  双(1,2-儿茶酚-O,O′)-[(N-甲基乙酰胺基)甲基-C,O]硅酸盐和双(1,2-儿茶酚-O,O′)-[(2-氧代六氢氮杂卓-1-基)甲基-C、O]硅酸酯是在二环己基胺存在下，通过焦儿茶酚对相应的三甲氧基硅烷衍生物进行酯交换反应而合成的。根据 X 射线衍射数据，合成盐是阴离子硅配合物，其中的硅原子由于两个（O,O′）二阴离子和一个（C,O）单阴离子螯合配体而具有六配位。在后者中，由于分子内（离子内）配位键 O→Si 的形成而发生螯合作用。
• Synthesis, Structure and Electrochemical Properties of Acetamide- and Caprolactam-Containing Silicon Catecholates
  作者：Eugenia P. Kramarova、Alexander D. Volodin、Vadim V. Negrebetsky、Anastasia D. Shagina、Teimur M. Aliev、Pavel V. Dorovatovskii、Roman A. Novikov、Anna V. Vologzhanina、Alexander A. Korlyukov

  DOI：10.3390/molecules26123548

  日期：——

  Hexacoordinated heteroligand silicon catecholates, although being prospective as easily soluble compounds with high hydrolytic stability and diverse redox properties, have been insufficiently studied. The transesterification of 1-(trimethoxysilylmethyl)-2-oxohexahydroaze or N-methyl-N-(trimethoxysilylmethyl)acetamide by two equivalents of catechol derivatives in the presence of dicyclohexylamine afforded

  六配位杂配体硅儿茶酚酸盐虽然作为具有高水解稳定性和多种氧化还原特性的易溶化合物具有前景，但尚未得到充分研究。在二环己胺存在下，1-(三甲氧基甲硅烷基甲基)-2-氧代六氢aze或N-甲基-N- (三甲氧基甲硅烷基甲基)乙酰胺与2当量邻苯二酚衍生物发生酯交换反应，得到一系列目标化合物，收率良好。使用元素分析、FTIR、1 H、13 C 和29 Si NMR 光谱、X 射线晶体学和循环伏安法对配合物进行了表征。X 射线衍射证实硅原子具有SiCO 5的八面体几何形状根据29 Si NMR 数据，在溶液中保持不变的多面体。这些化合物表现出多达三个氧化波；并且还原曲线很大程度上取决于儿茶酚酸盐阴离子上取代基的性质。
• Synthesis, structure and muscarinic agonist activity of substituted<i>N</i>-(silatran-1-ylmethyl)acetamides
  作者：Vera G. Pukhalskaya、Eugeniya P. Kramarova、Larisa P. Kozaeva、Alexander A. Korlyukov、Alexander G. Shipov、Sergey Yu. Bylikin、Vadim V. Negrebetsky、Gennady V. Poryadin、Yuri I. Baukov

  DOI：10.1002/aoc.1539

  日期：2010.3

  N‐(silatran‐1‐ylmethyl)acetamides, N‐methyl‐N‐[1‐(3′,7′,10′‐trimethylsilatran‐1‐yl)methyl]acetamide (2a) and N‐(2‐hydroxyethyl)‐N‐[1‐(3′,7′,10′‐trimethylsilatran‐1‐yl)methyl]acetamide (2b) were prepared by the reactions of triisopropanolamine with N‐methyl‐N‐(trimethoxysilylmethyl)acetamide (1a) and 2,2‐dimethoxy‐4‐acetyl‐1‐oxa‐4‐aza‐2‐silacyclohexane (1b), respectively. According to X‐ray data, the structures of the

  取代的N-（silatran-1-基甲基）乙酰胺，N-甲基-N- [1-（3'，7'，10'-三甲基silatran- 1-基）甲基]乙酰胺（2a）和N-（2-羟基乙基） ）-三异丙醇胺与N-甲基-N的反应制备了N- [1-（1'（3'，7'，10'-三甲基硅氧杂环丁-1-基）甲基]乙酰胺（2b）（三甲氧基甲硅烷基甲基）乙酰胺（1a）和2,2-二甲氧基-4-乙酰基-1-氧杂-4-氮杂-2-硅环己烷（1b）。根据X射线数据，甲硅烷基部分的结构是不对称和对称立体异构体的叠加。两种化合物中都没有中心原子与环外取代基之间的O→Si配位。Silatranes 2a和2b是部分毒蕈碱激动剂，通过直接与回肠平滑肌的胆碱受体结合，显示出次最大的作用并模仿了乙酰胆碱的作用。版权所有©2009 John Wiley＆Sons，Ltd.
• Shipov, A. G.; Kramarova, E. P.; Artamkina, O. B., Russian Journal of General Chemistry, 1993, vol. 63, # 6.2, p. 1002
  作者：Shipov, A. G.、Kramarova, E. P.、Artamkina, O. B.、Baukov, Yu. I.

  DOI：——

  日期：——