苯甲胺,N-(3-甲基亚丁基)-,N-氧化 | 162365-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 苯甲胺,N-(3-甲基亚丁基)-,N-氧化
• 英文名称: (Z)-N-(3-methylbutylidene)benzylamine N-oxide
• 英文别名: N-benzyl-3-methylbutan-1-imine oxide
• CAS: 162365-56-2；162740-13-8
• 化学式: C₁₂H₁₇NO
• 分子量: 191.273
• InChiKey: ZWTXJNHNOFDUSX-LCYFTJDESA-N

物化性质

• 沸点：
  374.6±12.0 °C(Predicted)
• 密度：
  0.967±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  28.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  苯甲胺,N-(3-甲基亚丁基)-,N-氧化 在 N-碘代丁二酰亚胺 、 锌 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 Acetic acid (3S,4S,5R)-2-benzyl-5-iodomethyl-3-isobutyl-isoxazolidin-4-yl ester
  参考文献：
  名称：

  3-Bromo-propenyl acetate in organic synthesis: an expeditious route to 3-alkyl-4-acetoxy-5-iodomethyl isoxazolidines

  摘要：

  N-Trimethylsilyloxy-N-benzyl-1-alkyl-2-acetoxy-3-buten-1-amines 13, obtained in good yields and moderate diastereo-selectivities by TMSOTf promoted alpha-acetoxyallylation of nitrones using metallic zinc and 3-bromo-propenyl acetate 11, are exploited in a stereospecific 5-exo-trig iodocyclization reaction to afford 4,5-eis-3-alkyl-4-acetoxy-5-iodomethyl isoxazolidines 14, promising starting materials for the synthesis of pyrrolidine azasugars. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.04.004
• 作为产物：
  描述：

  N-苄基羟胺 、 异戊醛 在 magnesium sulfate 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以84%的产率得到苯甲胺,N-(3-甲基亚丁基)-,N-氧化
  参考文献：
  名称：

  Synthesis of N-Benzyl Nitrones

  摘要：

  A general procedure for the synthesis of twenty-seven chiral and achiral N-benzyl nitrones 1 is described.

  DOI：

  10.1080/00397919408010565

文献信息

• Nucleophilic Addition of Nitrones to Ketones: Development of a New Catalytic Asymmetric Nitrone-Aldol Reaction
  作者：Anders Bøgevig、Kurt V. Gothelf、Karl Anker Jørgensen

  DOI：10.1002/1521-3765(20021216)8:24<5652::aid-chem5652>3.0.co;2-j

  日期：2002.12.16

  The scope and potential of the reaction have been investigated and developed. The reaction can also be catalyzed by secondary amines. The use of chiral cyclic amines, such as L-proline leads to optically active beta-hydroxynitrones in moderate yield and with moderate to high enantiomeric excess. The reaction mechanism was studied by kinetic measurements, intermediate and product analysis, and determination

  已经发现了一种新的有机反应，其中硝酮在醛缩型反应中与羰基化合物反应，得到官能化的β-羟基硝酮。硝酮的α-碳原子与缺乏电子的酮（如α-酮酸酯，α，β-二酮和三氟甲基酮）进行亲核加成反应，从而以中等至良好的收率提供产物。已经研究和开发了反应的范围和潜力。该反应也可以通过仲胺催化。手性环状胺，例如L-脯氨酸的使用导致中等产率和中等至高对映体过量的光学活性β-羟基硝酮。通过动力学测量，中间体和产物分析以及确定产物的绝对构型来研究反应机理。
• Samarium Diiodide-Induced Asymmetric Synthesis of Optically Pure Unsymmetrical Vicinal Diamines by Reductive Cross-Coupling of Nitrones with <i>N</i>-<i>tert</i>-Butanesulfinyl Imines
  作者：Yu-Wu Zhong、Ming-Hua Xu、Guo-Qiang Lin

  DOI：10.1021/ol048444d

  日期：2004.10.1

  [reaction: see text] An efficient method for the preparation of optically pure unsymmetrical vicinal diamines by the SmI(2)-induced reductive cross-coupling of nitrones with chiral N-tert-butanesulfinyl imines was developed. This is the first successful example of the highly diastereoselective and enantioselective cross-coupling between two different imine species. It provides a straightforward access

  [反应：见正文]开发了一种有效的方法来制备光学纯的不对称邻二胺，该方法是通过SmI（2）诱导的硝酮与手性N-叔丁烷亚磺酰基亚胺的还原交叉偶联。这是两个不同亚胺类之间高度非对映选择性和对映选择性交叉偶联的第一个成功实例。它提供了直接访问广泛用于不对称合成的对映纯不对称邻二胺的方法。
• Nitrones in Organic Synthesis. Synthesis of Secondary Allyl Amines
  作者：A. Dondoni、F. L. Merchán、P. Merino、T. Tejero

  DOI：10.1080/00397919408010566

  日期：1994.10

  Abstract Nitrones 1 undergo addition of vinyl organomagnesium bromide to give the allyl hydroxylamines 3 which are easily reduced to the corresponding N-benzyl allyl amines 2.

  摘要 硝酮 1 与乙烯基有机溴化镁加成得到烯丙基羟胺 3，后者很容易还原为相应的 N-苄基烯丙基胺 2。
• A method for the generation of a dynamic combinatorial library using nitrones
  申请人：Therascope AG

  公开号：EP1496038A1

  公开（公告）日：2005-01-12

  The present invention relates to a method of forming a dynamic combinatorial library of compounds which are potentially capable of binding to a target, which method comprises i) selecting one first set of molecules which molecules each carry at least one hydroxylamine function; ii) selecting at least one further set of molecules which molecules carry at least one carbonyl function; iii) reacting the two sets of molecules with each other and at least temporarily in the presence of the target, under conditions where a reversible formation of nitrone functions between the hydroxylamine function and the carbonyl function on the molecules forming each of the sets occurs. Pharmaceutically active compounds which are formed when the library is generated can be identified by analysing the library, preferably by comparing the amounts of the compounds formed in the presence of the target and in the absence of the target.

  本发明涉及一种形成动态组合化合物库的方法，这些化合物可能能够与靶标结合，该方法包括i) 选择一组分子，这些分子每个携带至少一个羟胺基团；ii) 选择至少一个进一步的分子组，这些分子携带至少一个酮基团；iii) 在靶标的存在下，将这两组分子在至少暂时的条件下相互反应，其中在形成每个组中的分子之间的羟胺基团和酮基团之间的氮酮功能的可逆形成条件下发生。通过分析该库，特别是通过比较在存在靶标和不存在靶标的情况下形成的化合物的数量，可以确定在生成库时形成的具有药用活性的化合物。
• A Short Synthesis of γ-Amino Acids from Nitrones; Synthesis of Vigabatrin®
  作者：Christelle Dagoneau、Axel Tomassini、Jean-Noël Denis、Yannick Vallée

  DOI：10.1055/s-2001-9758

  日期：——

  Treatment of the γ-N-hydroxylamino-α,β-acetylenic esters, obtained by the reaction of nitrones with alkyl 3-lithiopropiolates, with H2 over Raney nickel, followed by in situ protection of the formed amines, gives N-Boc-γ-amino esters. This method has been applied to a synthesis of (S) and (R)-Vigabatrin®.

  在雷尼镍上用 H2 处理通过硝基烷基 3-硫代丙酸酯与δ-N-羟基氨基-δ,δ-乙炔酯反应得到的δ-N-羟基氨基-δ,δ-乙炔酯，然后对形成的胺进行原位保护，得到 N-叔丁氧羰基-δ-氨基酯。这种方法已用于合成 (S) 和 (R)-Vigabatrin® 。