[bis(2-methoxyethyl)amino]trimethylsilane | 221557-49-9

• 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: [bis(2-methoxyethyl)amino]trimethylsilane
• 英文别名: N-trimethylsilyl bis(2-methoxyethyl)amine；bis(2-methoxyethyl)(trimethylsilyl)amine；2-methoxy-N-(2-methoxyethyl)-N-trimethylsilylethanamine
• CAS: 221557-49-9
• 化学式: C₉H₂₃NO₂Si
• 分子量: 205.373
• InChiKey: KUEVJJWRLIEXTJ-UHFFFAOYSA-N

物化性质

• 沸点：
  216.0±25.0 °C(Predicted)
• 密度：
  0.882±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.42
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  [bis(2-methoxyethyl)amino]trimethylsilane 在 sulfur tetrafluoride 作用下， 以 乙醚 为溶剂， 以70%的产率得到[双(2-甲氧基乙基)胺]三氟化硫
  参考文献：
  名称：

  Bis(2-methoxyethyl)aminosulfur trifluoride: a new broad-spectrum deoxofluorinating agent with enhanced thermal stability

  摘要：

  双(2-甲氧乙基)氨基硫三氟化物（Deoxo-FluorTM）在将醇转化为烷基氟化物、将醛/酮转化为相应的双氟化物，以及将羧酸转化为其三氟甲基衍生物方面有效；它是传统的二烷基氨基硫三氟化物（DAST）脱氧氟化试剂的一个热敏感性较低、适用范围更广的替代品。

  DOI：

  10.1039/a808517j
• 作为产物：
  描述：

  三甲基氯硅烷 、 双(2-甲氧基乙基)胺 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 [bis(2-methoxyethyl)amino]trimethylsilane
  参考文献：
  名称：

  芳烃，氨基硅烷和醛的三组分偶联。

  摘要：

  芳烃，氨基硅烷和醛的三组分偶联使得各种氨基和羟甲基可以直接引入芳香环的1,2-位。

  DOI：

  10.1021/ol071347a

文献信息

• Ni-Catalyzed Carbon–Carbon Bond-Forming Reductive Amination
  作者：Christoph Heinz、J. Patrick Lutz、Eric M. Simmons、Michael M. Miller、William R. Ewing、Abigail G. Doyle

  DOI：10.1021/jacs.7b12212

  日期：2018.2.14

  describes a three-component, Ni-catalyzed reductive coupling that enables the convergent synthesis of tertiary benzhydryl amines, which are challenging to access by traditional reductive amination methodologies. The reaction makes use of iminium ions generated in situ from the condensation of secondary N-trimethylsilyl amines with benzaldehydes, and these species undergo reaction with several distinct classes

  本报告描述了一种三组分、Ni 催化的还原偶联，它能够聚合合成二苯甲基叔胺，这是传统还原胺化方法难以获得的。该反应利用仲 N-三甲基甲硅烷基胺与苯甲醛缩合原位生成的亚胺离子，这些物质与几种不同类别的有机亲电试剂发生反应。抗偏头痛药物氟桂利嗪 (Sibelium) 的一步合成以及帕罗西汀 (Paxil) 和美托洛尔 (Lopressor) 的高产衍生化证明了该工艺的合成价值。机理研究支持顺序氧化加成机制，而不是通过 α-氨基自由基形成进行的途径。因此，
• Three-Component Coupling Using Arynes and Aminosilanes for ortho-Selective Double Functionalization of Aromatic Skeletons
  作者：Takami Morishita、Hiroyuki Fukushima、Hiroto Yoshida、Joji Ohshita、Atsutaka Kunai

  DOI：10.1021/jo800761b

  日期：2008.7.1

  Arynes were found to couple with aminosilanes and carbonyl compounds in the presence of benzoic acid to provide 2-aminobenzhydrols. Sulfonylimines could also be applied to the reaction, enabling amino and aminomethyl moieties to be incorporated into contiguous positions of aromatic skeletons. Only a small amount of the three-component coupling product was obtained in the absence of benzoic acid, which

  发现在苯甲酸存在下，芳烃与氨基硅烷和羰基化合物偶合，以提供2-氨基苯甲酚。磺酰亚胺还可以应用于反应中，使氨基和氨基甲基部分可以并入芳香族骨架的连续位置。在不存在苯甲酸的情况下，仅获得少量的三组分偶联产物，这证实了其在本反应中的重要作用。
• Neutral and cationic rare-earth metal alkyl complexes that contain bis(2-methoxyethyl)(trimethylsilyl)amine, a neutral [ONO]-type ligand
  作者：Peter M. Zeimentz、Thomas P. Spaniol、Jun Okuda

  DOI：10.1016/j.ica.2006.04.018

  日期：2006.12

  Neutral tris(trimethylsilylmethyl) complexes [Ln(CH(2)SiMC(3))(3)(L)] (Ln = Sc (1), Lu (2)) and cationic bis(trimethylsilylmethyl) complexes [Ln(CH(2)SiMe(3))(2)(L)(THF)](+)[BPh(4)](-), (Ln = Sc (3), Lu (4)) that contain bis(2-methoxyethyl)(trimethylsilyl)amine (L = Me(3)SiN(CH(2)-CH(2)OMe)(2)) as a neutral, tridentate ligand were synthesized and characterized by NMR spectroscopy. X-ray structural analysis was performed for the scandium complex 1 and exhibited a distorted octahedral coordination geometry with a facially arranged ligand at the neutral scandium center. NMR spectroscopy corroborated the coordination of the tertiary amine function of the ligand to the metal. Complexes 3 and 4 expand the still limited range of cationic rare-earth metal alkyl complexes with known neutral, multidentate ligands. (c) 2006 Elsevier B.V. All rights reserved.
• Bis(2-methoxyethyl)aminosulfur Trifluoride:  A New Broad-Spectrum Deoxofluorinating Agent with Enhanced Thermal Stability
  作者：Gauri S. Lal、Guido P. Pez、Reno J. Pesaresi、Frank M. Prozonic、Hansong Cheng

  DOI：10.1021/jo990566+

  日期：1999.9.1

  Bis(2-methoxyethyl)aminosulfur trifluoride, (CH3OCH2CH2)(2)NSF3 (Deoxo-Fluor reagent), is a new deoxofluorinating agent that is much more thermally stable than DAST (C2H5)(2)NSF3 and its congeners. It is effective for the conversion of alcohols to alkyl fluorides, aldehydes/ketones to the corresponding gem-difluorides, and carboxylic acids to the trifluoromethyl derivatives with, in some cases, superior performance compared to DAST. The enhanced stability is rationalized on the basis of conformational rigidity imposed by a coordination of the alkoxy groups with the electron-deficient sulfur atom of the trifluoride.
• Three-Component Coupling of Arynes, Aminosilanes, and Aldehydes
  作者：Hiroto Yoshida、Takami Morishita、Hiroyuki Fukushima、Joji Ohshita、Atsutaka Kunai

  DOI：10.1021/ol071347a

  日期：2007.8.1

  A three-component coupling of arynes, aminosilanes, and aldehydes enables diverse amino and hydroxymethyl groups to be incorporated directly into 1,2-positions of aromatic rings.

  芳烃，氨基硅烷和醛的三组分偶联使得各种氨基和羟甲基可以直接引入芳香环的1,2-位。