(Z)-N-tert-butyl-1-phenylmethanimine oxide-d | 183969-55-3

• 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: (Z)-N-tert-butyl-1-phenylmethanimine oxide-d
• CAS: 183969-55-3
• 化学式: C₁₁H₁₅NO
• 分子量: 178.238
• InChiKey: IYSYLWYGCWTJSG-MTTAZUJSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.41
• 重原子数：
  13.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (Z)-N-tert-butyl-1-phenylmethanimine oxide-d 在 tetraphenylphosphonium hexachloroosmate(V) 、 azanium,dinitroazanide 作用下， 以 乙腈 为溶剂， 生成
  参考文献：
  名称：

  Reaction between Dinitroamide Ion and the Radical Cation of N-tert-Butyl-alpha-phenylnitrone. Formal Elimination of Nitrous Acid from a Spin Adduct.

  摘要：

  Dinitroamide ion was oxidized at a potential of 2.3-2.4 V and reduced at -0.4 V (Ag/AgCl reference electrode). The photochemical oxidation of a solution of a dinitroamide salt and the spin trap, N-tert-butyl-alpha-phenylnitrone (PBN), in acetonitrile or dichloromethane gave rise to a weak 3 x 5 lines EPR spectrum, assigned to the formal spin adduct of dinitroamino radical and PEN, (NO2)(2)N-PBN'. The reaction is suggested to involve oxidation of PEN to its radical cation, followed by capture of dinitroamide ion by the latter. The thermal oxidation of similar solutions gave rise to a different, much more intense EPR spectrum, the hyperfine splitting constants of which showed the presence of three different nitrogens and the absence of the v.-hydrogen of PEN. The spectrum was assigned to O2N-N=C(Ph)-N(O')(Bu-t), formally derived from the dinitroamino spin adduct by elimination of nitrous acid. Mechanistically, this transformation presumably occurs by one-electron oxidation of (NO2)(2)N-PBN', followed by loss of a proton and NO2, from the nitrosonium ion intermediate formed.

  DOI：

  10.3891/acta.chem.scand.52-0207
• 作为产物：
  描述：

  Deoxybenzoin-d₂ 在 sodium periodate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 (Z)-N-tert-butyl-1-phenylmethanimine oxide-d
  参考文献：
  名称：

  N，N-二取代羟胺不对称氧化汞（II）的区域化学

  摘要：

  N，N-二取代的羟胺分别被具有一个和两个氢原子的α和α'碳原子氧化的汞（II）氧化，以高度区域选择性的方式生成醛亚硝酮。如初生动力学同位素效应所示，速率确定步骤涉及α质子的去除。

  DOI：

  10.1016/0040-4020(96)00904-0

文献信息

• Regiochemistry of mercury(II) oxide oxidation of unsymmetrical N,N-disubstituted hydroxylamines
  作者：Sk.Asrof Ali、S.M. Azhar Hashmi、Mohammad N. Siddiqui、Mohammed I.M. Wazeer

  DOI：10.1016/0040-4020(96)00904-0

  日期：1996.11

  Mercury(II) oxide oxidation of N,N-disubstituted hydroxylamines with the α and α′ carbon atoms containing one and two hydrogen atoms, respectively, gave aldonitrones in a highly regioselective manner. Removal of the α proton is involved in the rate determining step as shown by primary kinetic isotope effect.

  N，N-二取代的羟胺分别被具有一个和两个氢原子的α和α'碳原子氧化的汞（II）氧化，以高度区域选择性的方式生成醛亚硝酮。如初生动力学同位素效应所示，速率确定步骤涉及α质子的去除。
• Reaction between Dinitroamide Ion and the Radical Cation of N-tert-Butyl-alpha-phenylnitrone. Formal Elimination of Nitrous Acid from a Spin Adduct.
  作者：Lennart Eberson、Ulla Pretzmann、Bente Nielsen、Carl Erik Olsen、Inger Søtofte、George W. Francis、József Szúnyog、Bengt Långström

  DOI：10.3891/acta.chem.scand.52-0207

  日期：——

  Dinitroamide ion was oxidized at a potential of 2.3-2.4 V and reduced at -0.4 V (Ag/AgCl reference electrode). The photochemical oxidation of a solution of a dinitroamide salt and the spin trap, N-tert-butyl-alpha-phenylnitrone (PBN), in acetonitrile or dichloromethane gave rise to a weak 3 x 5 lines EPR spectrum, assigned to the formal spin adduct of dinitroamino radical and PEN, (NO2)(2)N-PBN'. The reaction is suggested to involve oxidation of PEN to its radical cation, followed by capture of dinitroamide ion by the latter. The thermal oxidation of similar solutions gave rise to a different, much more intense EPR spectrum, the hyperfine splitting constants of which showed the presence of three different nitrogens and the absence of the v.-hydrogen of PEN. The spectrum was assigned to O2N-N=C(Ph)-N(O')(Bu-t), formally derived from the dinitroamino spin adduct by elimination of nitrous acid. Mechanistically, this transformation presumably occurs by one-electron oxidation of (NO2)(2)N-PBN', followed by loss of a proton and NO2, from the nitrosonium ion intermediate formed.