2,4,6-tris(t-butyl)phenyl N-(2-trimethylsilylethyl)carbamate | 855297-19-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,4,6-tris(t-butyl)phenyl N-(2-trimethylsilylethyl)carbamate
• 英文别名: (2,4,6-tritert-butylphenyl) N-(2-trimethylsilylethyl)carbamate
• CAS: 855297-19-7
• 化学式: C₂₄H₄₃NO₂Si
• 分子量: 405.696
• InChiKey: PSIMQVVYUJXDKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.01
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,4,6-tris(t-butyl)phenyl N-(2-trimethylsilylethyl)carbamate 在 乙酸酐 、 溶剂黄146 、 sodium nitrite 作用下， 反应 14.0h， 以84%的产率得到2,4,6-tris(t-butyl)phenyl N-(2-trimethylsilylethyl)-N-nitrosocarbamate
  参考文献：
  名称：

  Synthesis, structural studies and desilylation reactions of some N-2-(trimethylsilyl)ethyl-N-nitrosocarbamates

  摘要：

  The present report describes the preparation and characterization of several N-2-(trimethylsilyl)ethyl-N-nitrosocarbamates, designed as precursors to thermally unstable secondary N-nitrosocarbamate anions via fluoride-assisted cleavage. X-ray structural studies demonstrate that the core N-nitrosocarbamate moiety has a nearly planar geometry, with an s-E orientation at the N-N bond. DFT calculations (B3LYP/6-31+G(d)) reproduce accurately the structural features of the title compounds and detailed conformational analysis at the same level of theory addresses the long-standing issue of preferred geometries for three classes of related structures: N-nitrosocarbamates, N-nitrosoureas and N-nitrosoamides. Desilylation studies demonstrate that both the solvent and the fluoride concentration influence the rate of the process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.044
• 作为产物：
  描述：

  2-(三甲基甲硅烷基)乙胺 、 2,4,6-tri(tert-butyl)phenyl carbonochloridate 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以45%的产率得到2,4,6-tris(t-butyl)phenyl N-(2-trimethylsilylethyl)carbamate
  参考文献：
  名称：

  Synthesis, structural studies and desilylation reactions of some N-2-(trimethylsilyl)ethyl-N-nitrosocarbamates

  摘要：

  The present report describes the preparation and characterization of several N-2-(trimethylsilyl)ethyl-N-nitrosocarbamates, designed as precursors to thermally unstable secondary N-nitrosocarbamate anions via fluoride-assisted cleavage. X-ray structural studies demonstrate that the core N-nitrosocarbamate moiety has a nearly planar geometry, with an s-E orientation at the N-N bond. DFT calculations (B3LYP/6-31+G(d)) reproduce accurately the structural features of the title compounds and detailed conformational analysis at the same level of theory addresses the long-standing issue of preferred geometries for three classes of related structures: N-nitrosocarbamates, N-nitrosoureas and N-nitrosoamides. Desilylation studies demonstrate that both the solvent and the fluoride concentration influence the rate of the process. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.03.044