N,N-bis(trimethylsilyl)-glycine trimethylsilyl ester | 5630-82-0

• 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 trimethylsilyl ester
• 英文别名: N,N-bis(trimethylsilyl)glycine trimethylsilyl ester；N,N-Bis(trimethylsilyl)glycine trimethylsilylester；N,N-Bis(trimethylsilyl)glycin-trimethylsilylester；N,N,O-Trimethylsilylglycine；glycine TMS；N,N-Bis-(trimethylsilyl)-glycin-trimethylsilylester；Trimethylsilyl [bis(trimethylsilyl)amino]acetate；trimethylsilyl 2-[bis(trimethylsilyl)amino]acetate
• CAS: 5630-82-0
• 化学式: C₁₁H₂₉NO₂Si₃
• 分子量: 291.613
• InChiKey: YVBMCPFZLGEMJT-UHFFFAOYSA-N

物化性质

• 沸点：
  108-109 °C(Press: 12 Torr)
• 密度：
  0.888±0.06 g/cm3(Predicted)
• 保留指数：
  1317;1315.88;1326.3

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  1-bromo-4-nitrobutane 、 N,N-bis(trimethylsilyl)-glycine trimethylsilyl ester 生成
  参考文献：
  名称：

  合成肽6-硝基-2-氨基己酮

  摘要：

  DOI：

  10.1016/s0040-4039(01)86804-0
• 作为产物：
  描述：

  三甲基硅烷基二乙胺 、 聚甘氨酸 生成 N,N-bis(trimethylsilyl)-glycine trimethylsilyl ester
  参考文献：
  名称：

  用-双（三甲基甲硅烷基）氨基乙烯酮双（三甲基甲硅烷基）乙缩醛或其-甲基-三甲基甲硅烷基类似物合成α-氨基-β-羟基酸

  摘要：

  在三氟甲磺酸三甲基甲硅烷基酯的存在下，标题化合物与醛和酮的缩合以非对映异构体混合物的形式以相当高的收率提供了相应的α-氨基-β-羟基酸。

  DOI：

  10.1016/s0040-4039(00)83885-x

文献信息

• 29Si and13C NMR spectra of trimethylsilylated amino acids
  作者：Jan Schraml、Magdalena Kvíčalová、Iveta Schwarzová、Jan Velíšek

  DOI：10.1002/mrc.1260321005

  日期：1994.10

  The 29Si and 13C NMR chemical shifts are reported for trimethylsilyl derivatives of 25 amino acids, the majority of which occur naturally as protein constituents of foodstuffs. The 29Si chemical shifts in trimethylsilyl esters of amino acids roughly correlate linearly with the pK values of the parent amino acid. No such simple correlations were found for the shifts in the fully trimethylsilylated amino

  报告了 25 种氨基酸的三甲基甲硅烷基衍生物的 29Si 和 13C NMR 化学位移，其中大部分作为食品的蛋白质成分天然存在。氨基酸的三甲基甲硅烷基酯中的 29Si 化学位移与母体氨基酸的 pK 值大致呈线性相关。对于完全三甲基甲硅烷基化氨基酸的变化，没有发现这种简单的相关性。遇到的各种官能团的 29Si 化学位移属于不同的光谱区域，但 (CH3)3SiN 或 (CH3)3SiOOC 基团的位移单独不足以识别酸，但在大多数情况下它们的组合是。
• Glycine Imine—The Elusive <i>α</i> ‐Imino Acid Intermediate in the Reductive Amination of Glyoxylic Acid
  作者：Viktor Paczelt、Raffael C. Wende、Peter R. Schreiner、André K. Eckhardt

  DOI：10.1002/anie.202218548

  日期：2023.3.6

  2-Iminoacetic acid or glycine imine is a proposed key intermediate in the reductive amination of glyoxylic acid. In contrast to well-known α-amino acids the compound class of α-imino acids is not much explored and not well-characterized. Glycine imine was prepared through photochemical denitrogenation of 2-azidoacetic acid, spectroscopically characterized, and its reactivity studied in aqueous solution

  2-亚氨基乙酸或甘氨酸亚胺是乙醛酸还原胺化的关键中间体。与众所周知的α-氨基酸相比， α-亚氨基酸的化合物类别没有太多探索，也没有很好地表征。通过2-叠氮乙酸的光化学脱氮制备甘氨酸亚胺，对其进行光谱表征，并研究其在水溶液中的反应性。
• Schorr, Manfred; Schmitt, Wilfried, Phosphorus, Sulfur and Silicon and the Related Elements, 1992, vol. 68, # 1-4, p. 25 - 36
  作者：Schorr, Manfred、Schmitt, Wilfried

  DOI：——

  日期：——
• Synthesis of (4)-4-(()-2-butenyl)-4,-dimethyl--threonine (MeBMT), the characteristic amino acid of cyclosporine
  作者：Ulrich Schmidt、Wolfgang Siegel

  DOI：10.1016/s0040-4039(00)96225-7

  日期：1987.1
• Lipase-Catalyzed Enantiomeric Resolution of Ceramides
  作者：Mikio Bakke、Masahiro Takizawa、Takeshi Sugai、Hiromichi Ohta

  DOI：10.1021/jo980727u

  日期：1998.10.1

  Lipase-catalyzed enantiomeric kinetic resolution of ceramides related to C-16-sphinganine and C-18-sphingenine is described. Two hydroxy groups in readily available racemic N-stearoyl-erythro-C-16-sphinganine were acetylated, and several kinds of lipases were screened for the hydrolysis of this substrate. Among them, a Burkholderia cepacia lipase (SC lipase A, Sumitomo Chemical Co., Ltd.) showed the highest reactivity and enantioselectivity. The rate of hydrolysis and selectivity were greatly affected by some additives. Especially, the combined use of a detergent, Triton X-100, and the solid support, Florisil, for immobilization showed the highest enantioselectivity (E = ca. 170), although the reaction rate turned low. Introduction of a double bond into the substrate (N-stearoyl-erythro-C-18-sphingenine) also retarded the hydrolysis. By utilizing the preferential hydrolysis of the acetate on the primary hydroxy group, another advantageous feature of this enzyme-catalyzed reaction, the resulting product could directly be used as the glycosyl acceptor for cerebroside synthesis.

表征谱图