N,N-bis(trimethylsilyl)glycine ethyl ester | 20836-51-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N,N-bis(trimethylsilyl)glycine ethyl ester
• 英文别名: Ethyl [bis(trimethylsilyl)amino]acetate；ethyl 2-[bis(trimethylsilyl)amino]acetate
• CAS: 20836-51-5
• 化学式: C₁₀H₂₅NO₂Si₂
• 分子量: 247.485
• InChiKey: YBWBKYMQYUTNMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  碘甲基三甲基硅烷 、 N,N-bis(trimethylsilyl)glycine ethyl ester 生成 2-(1,1,1,3,3,3-Hexamethyl-disilazan-2-yl)-3-trimethylsilanyl-propionic acid ethyl ester
  参考文献：
  名称：

  Kaufmann,K.-D. et al., Zeitschrift fur Chemie, 1970, vol. 10, p. 392 - 393

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基硅烷基二乙胺 、 2-胺基乙酸乙酯 在 硫酸氢铵 作用下， 生成 N,N-bis(trimethylsilyl)glycine ethyl ester
  参考文献：
  名称：

  Ruehlmann,K.; Kuhrt,G., Angewandte Chemie, 1968, vol. 80, p. 797 - 798

  摘要：

  DOI：

文献信息

• Stereoselective one-pot syntheses of trans-3-amino-β-lactams from zinc enolates of N-protected α-aminoacid esters and imines.
  作者：Fred H van der Steen、Johann T.B.H Jastrzebski、Gerard van Koten

  DOI：10.1016/s0040-4039(00)87909-5

  日期：1988.1

  A new one-pot synthesis of 3-aminoβ-lactams that is based on the condensation of simple imines with zinc enolates of disilyl protected glycine esters is reported. Isolated yields are high and a trans-selectivity is observed.

  报道了一种新的一锅法合成3-氨基β-内酰胺的方法，该方法基于简单的亚胺与二甲硅烷基保护的甘氨酸酯的烯醇锌的缩合反应。分离的产率高并且观察到反式选择性。
• FUNCTIONALIZED POLYMERS AND METHODS FOR THEIR MANUFACTURE
  申请人：Luo Steven

  公开号：US20110077325A1

  公开（公告）日：2011-03-31

  A method for preparing a functionalized polymer, the method comprising the steps of (i) polymerizing monomer with a coordination catalyst to form a reactive polymer; and (ii) reacting the reactive polymer with a carboxylic or thiocarboxylic ester containing a silylated amino group.

  一种制备功能化聚合物的方法，包括以下步骤：(i)使用配位催化剂聚合单体，形成反应性聚合物；(ii)将反应性聚合物与含有硅烷基氨基的羧酸酯或硫代羧酸酯反应。
• Functionalized polymers and methods for their manufacture
  申请人：Luo Steven

  公开号：US08895670B2

  公开（公告）日：2014-11-25

  A method for preparing a functionalized polymer, the method comprising the steps of (i) polymerizing monomer with a coordination catalyst to form a reactive polymer; and (ii) reacting the reactive polymer with a carboxylic or thiocarboxylic ester containing a silylated amino group.

  一种制备功能化聚合物的方法，包括以下步骤：（i）使用协同催化剂聚合单体，形成反应性聚合物；（ii）将反应性聚合物与含有硅化氨基的羧酸酯或硫代羧酸酯反应。
• A new and efficient route to 3-amino-2-azetidinones via zinc enolates of N,N-disubstituted glycine esters
  作者：Fred H. Van der Steen、Henk Kleijn、Johann T. B. H. Jastrzebski、Gerard Van Koten

  DOI：10.1021/jo00017a030

  日期：1991.8

  This report describes novel and efficient ''one-pot'' syntheses of 1-unsubstituted-3-amino-4-substituted-2-azetidinones (8 and 9) involving the in situ preparation of lithium and particularly zinc enolates (5 and 6, respectively) of N,N-disubstituted glycine esters (4) and subsequent reactions of these enolates with (simple) imines (7). Lithium enolates 5 only react with activated imines that are N-substituted with an electron-withdrawing group (e.g. aryl, trialkylsilyl), affording cis-3-amino-2-azetidinones in excellent yields with moderate to good stereoselectivity (de 68-92%). Zinc enolates 6 are more generally applicable since they react with activated imines as well as unactivated imines (e.g. those which are N-substituted with an electron-donating group such as alkyl) to afford 3-amino-2-azetidinones in excellent yields. The trans diastereoselectivity of the zinc-mediated enolate-imine condensation can be tuned by changing the steric and electronic properties of the substituents of the reagents (i.e. both enolate and imine), as well as the solvent polarity. The observed stereoselectivities are explained in terms of two highly ordered transition states, consisting of a Z-zinc ester enolate and an E-imine. Protection of the amino function of the metal enolates as a 2,2,5,5-tetramethyl-1-aza-2,5-disilacyclopentane ring affords 2-azetidinone products that can be easily deprotected to provide a free 3-amino function. In this way, trans-1-benzyl-3-(protected amino)-4-methyl-2-azetidinone (9a) and trans-3-(protected amino)-4-[(trimethylsilyl)ethynyl]-2-azetidinone (9g), key intermediates in the synthesis of Aztreonam (and 9g for bicyclic beta-lactam antibiotics as well), have been prepared in excellent yields (98 and 93%, respectively) with a high diastereoselectivity (de 82 and 94%, respectively). Furthermore, depending on the reactivity of imines 7, our method is also applicable using a catalytic amount (10 mol %) of ZnCl2.
• VAN, DER STEEN FRED H.;JASTRZEBSKI, JOHANN T. B. H.;VAN, KOTEN GERARD, TETRAHEDRON LETT., 29,(1988) N 20, 2467-2470
  作者：VAN, DER STEEN FRED H.、JASTRZEBSKI, JOHANN T. B. H.、VAN, KOTEN GERARD

  DOI：——

  日期：——