(Z)-α-Phenyl-N-(3-oxobutyl)nitrone | 38572-23-5

• 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)-α-Phenyl-N-(3-oxobutyl)nitrone
• 英文别名: N-(3-oxobutyl)-1-phenylmethanimine oxide
• CAS: 38572-23-5；143957-82-8
• 化学式: C₁₁H₁₃NO₂
• 分子量: 191.23
• InChiKey: BCHNYHOWDWNVJN-XFXZXTDPSA-N

物化性质

• 沸点：
  351.1±44.0 °C(Predicted)
• 密度：
  1.086±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (Z)-α-Phenyl-N-(3-oxobutyl)nitrone 、 乙酸酐 以32%的产率得到
  参考文献：
  名称：

  TIXONOV A. YA.; VOLODARSKIJ L. B., IZV. SIB. OTD. AN CCCP. CEP. XIM. N., 1979, HO 7/3, 144-147

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛肟 、 丁烯酮 在 三氟化硼乙醚 、 zinc(II) iodide 作用下， 以 二氯甲烷 为溶剂， 反应 7.0h， 以86%的产率得到(Z)-α-Phenyl-N-(3-oxobutyl)nitrone
  参考文献：
  名称：

  A new synthetic access to N-alkylated nitrones through Lewis acid-catalyzed conjugate additions of aldoximes

  摘要：

  In the presence of Lewis acid catalysts, aldoximes react with alpha,beta -unsaturated carbonyl compounds at room temperature to give N-alkylnitrones in good yields. Combination of two Lewis acid catalysts, zinc(II) iodide/boron trifluoride etherate (50 mol%/50 mol%), is the best choice to mediate the reactions producing N-alkylated nitrones in excellent yields. In this procedure, a variety of aldoximes and alpha,beta -unsaturated carbonyl acceptors can be employed. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)01346-6

文献信息

• Nitrones from addition of benzyl and allyl Grignard reagents to alkyl nitro compounds: chemo-, regio-, and stereoselectivity of the reaction
  作者：Giuseppe Bartoli、Enrico Marcantoni、Marino Petrini

  DOI：10.1021/jo00048a012

  日期：1992.10

  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.
• A new synthetic access to N-alkylated nitrones through Lewis acid-catalyzed conjugate additions of aldoximes
  作者：Kimitaka Nakama、Sumito Seki、Shuji Kanemasa

  DOI：10.1016/s0040-4039(01)01346-6

  日期：2001.9

  In the presence of Lewis acid catalysts, aldoximes react with alpha,beta -unsaturated carbonyl compounds at room temperature to give N-alkylnitrones in good yields. Combination of two Lewis acid catalysts, zinc(II) iodide/boron trifluoride etherate (50 mol%/50 mol%), is the best choice to mediate the reactions producing N-alkylated nitrones in excellent yields. In this procedure, a variety of aldoximes and alpha,beta -unsaturated carbonyl acceptors can be employed. (C) 2001 Elsevier Science Ltd. All rights reserved.
• TIXONOV A. YA.; VOLODARSKIJ L. B., IZV. SIB. OTD. AN CCCP. CEP. XIM. N., 1979, HO 7/3, 144-147
  作者：TIXONOV A. YA.、 VOLODARSKIJ L. B.

  DOI：——

  日期：——