N-tert-butyl-α-cyanobenzylhydroxylamine trimethylsilyl ether | 105488-71-9

• 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: N-tert-butyl-α-cyanobenzylhydroxylamine trimethylsilyl ether
• 英文别名: 2-[tert-butyl(trimethylsilyloxy)amino]-2-phenylacetonitrile
• CAS: 105488-71-9
• 化学式: C₁₅H₂₄N₂OSi
• 分子量: 276.454
• InChiKey: CILZMVRIIIRDMK-UHFFFAOYSA-N

物化性质

• 熔点：
  75-76 °C
• 沸点：
  317.6±35.0 °C(Predicted)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  36.26
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-tert-butyl-α-cyanobenzylhydroxylamine trimethylsilyl ether 在 lithium diisopropyl amide 作用下， 生成 N,N-Dimethyl-α-(t-butylimino)benzeneacetamide
  参考文献：
  名称：

  氰基-O-甲硅烷基羟胺作为硝酮保护基团

  摘要：

  三甲基氰硅烷到加法ñ -烷基- Ç -phenylnitrones得到氰基ö -silylhydroxylamines; 这些物质与氟化银的反应以定量收率再生了硝酮，从而提供了有用的硝酮保护基团。

  DOI：

  10.1039/c39860000789
• 作为产物：
  描述：

  三甲基氰硅烷 、 N-叔丁基-α-苯基硝酮 在 zinc(II) iodide 作用下， 以95%的产率得到N-tert-butyl-α-cyanobenzylhydroxylamine trimethylsilyl ether
  参考文献：
  名称：

  氰基-O-甲硅烷基羟胺作为硝酮保护基团

  摘要：

  三甲基氰硅烷到加法ñ -烷基- Ç -phenylnitrones得到氰基ö -silylhydroxylamines; 这些物质与氟化银的反应以定量收率再生了硝酮，从而提供了有用的硝酮保护基团。

  DOI：

  10.1039/c39860000789

文献信息

• Spin adduct formation from the spontaneous reaction between spin traps and weak electron acceptors, as exemplified by trichloroacetonitrile. An acid promoted version of the Forrester–Hepburn addition–oxidation mechanism
  作者：Lennart Eberson、John J. MacCullough、Ola Persson

  DOI：10.1039/a606864b

  日期：——

  The thermal reaction between N-tert-butyl-α-phenylnitrone (PBN) and trichloroacetonitrile is promoted by acids HA, giving spin adducts A–PBN˙ and CCl2CN–PBN˙, presumably via addition of HA to the nitrone with formation of a hydroxylamine and oxidation of the latter by trichloroacetonitrile (the Forrester–Hepburn mechanism).

  N-tert-butyl-α-phenylnitrone (PBN) 与三氯乙腈之间的热反应受到酸性 HA 的促进，产生自旋加合物 AâPBNË 和 CCl2CNâPBNË，可能是通过 HA 与腈酮加成，形成羟胺，后者被三氯乙腈氧化（ForresterâHepburn 机理）。
• Trapping of the Cyano Radical: Does it Ever Happen?
  作者：Lennart Eberson、Ola Persson、Vickie McKee、Christine J. McKenzie、Birgitte R. Rassing、Connie N. Rosendahl、Inger Søtofte、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0608

  日期：——

  The possible trapping of the cyano radical by alpha-phenyl-N-tert-butylnitrone (PBN) has been probed by a new method Tor the generation of CN., photolysis of N-cyanosuccinimide with PBN. Only in 1,1,1,3,3,3-hexafluoroprppan-2-ol was EPR spectral evidence obtained for the formation of a true spin adduct, namely the isocyano adduct of PBN. In other solvents, like dichloromethane or acetonitrile. the photolysis reaction took an entirely different course and gave the N-cyano-3-succinimidyl adduct of PBN and a second aminoxyl of unknown structure. The same pair of adducts could be obtained by photolysis of N-cyanomaleimide and PBN in a reductive coupling reaction. Maleimide gave a similar but clearly different pair of spectra.The possibility that the cyano or isocyano PBN adduct might undergo spontaneous hydrolysis to give the aminoformyl or formylamino adduct, respectively, was explored. It was shown that the authentic cyano adduct does not give the aminoformyl adduct under hydrolytic conditions. Since there is no method to prepare the isocyano adduct for such experiments, the problem of its hydrolytic reactivity is still open. The aminoformyl adduct of PBN was prepared by addition of the formamide anion to PBN, followed by oxidation by nickel peroxide, and characterized by its EPR spectrum.
• PADWA, A.;KOEHLER, K. F., J. CHEM. SOC. CHEM. COMMUN., 1986, N 10, 789-790
  作者：PADWA, A.、KOEHLER, K. F.

  DOI：——

  日期：——