N-(tert-Butyl)butylidenamin-N-oxid | 72552-75-1

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: N-(tert-Butyl)butylidenamin-N-oxid
• 英文别名: α-Propyl-N-tert-butylnitrone；N-(Butyliden)-tert.-butylamin-N-oxid；N-tert-butylbutan-1-imine oxide
• CAS: 72552-75-1
• 化学式: C₈H₁₇NO
• 分子量: 143.229
• InChiKey: JXISBLSMWZPVPM-UHFFFAOYSA-N

物化性质

• 沸点：
  50-53 °C(Press: 0.45 Torr)
• 密度：
  0.843±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  10.0
• 可旋转键数：
  2.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  N-(tert-Butyl)butylidenamin-N-oxid 生成 2-(tert-Butyl)-5-<(tert-butyl)(hydroxy)amino>-4-ethyl-3-propylisoxazolidin
  参考文献：
  名称：

  Aurich, Hans Guenter; Eidel, Joachim; Schmidt, Michael, Chemische Berichte, 1986, vol. 119, # 1, p. 18 - 35

  摘要：

  DOI：
• 作为产物：
  描述：

  1-硝基丁烷 、 magnesium,2-methylpropane,bromide 以 四氢呋喃 为溶剂， 反应 0.33h， 以15%的产率得到N-(tert-Butyl)butylidenamin-N-oxid
  参考文献：
  名称：

  Nitrones from addition of benzyl and allyl Grignard reagents to alkyl nitro compounds: chemo-, regio-, and stereoselectivity of the reaction

  摘要：

  Reaction of allyl and benzyl Grignard reagents with functionalized nitroalkanes affords nitrones in good yield. This process shows considerable chemoselectivity; carbonyl groups and other highly reactive electrophilic functions are unaffected by the reaction conditions (THF, -70-degrees-C). A mixture of regioisomers 4 and 5 is usually obtained, and the product distribution depends on the nature of the alkyl framework. An intermediate 3 is postulated, and the isomeric pair of nitrones arises, very likely through a selective syn elimination. Alpha-substituted alkyl chains give mostly conjugated products 4 while unbranched chains afford predominantly the nonconjugated nitrones 5. The 4/5 ratio can be strongly modified by using a proton source of suitable strength; trichloroacetic acid produces 4 exclusively in the reaction of nitroethane with benzyl Grignard, while 2,6-dimethylphenol affords completely the nonconjugated nitrone 5. The stereochemistry of the double bond is affected by the nature of the reagent used. Benzyl Grignard gives only Z nitrones 4 and 5; 2-butenylmagnesium chloride gives nonconjugated Z nitrones and a predominance of E isomer in the conjugated nitrone 5.

  DOI：

  10.1021/jo00048a012

文献信息

• Isoxazoline oxidation. An efficient method for the preparation of α,β-unsaturated carbonyl compounds
  作者：Albert Padwa、Donald N. Kline、John Perumattam

  DOI：10.1016/s0040-4039(00)95872-6

  日期：1987.1

  MCPBA peracid oxidation of Δ4-isoxazolines derived from the dipolar cycloaddition reaction of nitrones with acetylenes or allenes produces α,β-unsaturated ketones in excellent yield.

  MCPBA过酸Δ的氧化4个从与乙炔或丙二烯生产α，β不饱和酮的优良率硝酮的偶极环加成反应得到-isoxazolines。
• Synthesis of α-amidoketones. An application of the multi-hetero cope rearrangement
  作者：Ivan Lantos、wei-Yuan Zhang

  DOI：10.1016/0040-4039(94)88053-0

  日期：1994.8

  N-methylcarboximidoyl chloride affords after hydrolytic workup α-amidoketones. The results are interpreted in terms of the formation of an intermediate capable of undergoing a facile [3,3] sigmatropic rearrangement. Aldehyde derived nitrones form imides via a [3+2] cycloaddition reaction.

  水解后的α-酰胺酮使酮衍生的硝酮与N-甲基羧酰亚胺基氯缩合。结果的解释是根据中间体的形成，该中间体能够进行容易的[3,3]σ重排。醛衍生的硝酮通过[3 + 2]环加成反应形成酰亚胺。
• Torssell,K.; Zeuthen,O., Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1978, vol. 32, p. 118 - 124
  作者：Torssell,K.、Zeuthen,O.

  DOI：——

  日期：——