N-benzyl-2-methoxy-2-phenylacetamide | 62735-59-5

• 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: N-benzyl-2-methoxy-2-phenylacetamide
• CAS: 62735-59-5
• 化学式: C₁₆H₁₇NO₂
• 分子量: 255.316
• InChiKey: QSGVYIYVJWTCTD-UHFFFAOYSA-N

物化性质

• 熔点：
  82-83 °C
• 沸点：
  447.2±45.0 °C(Predicted)
• 密度：
  1.114±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  甲醇 、 N-(mesyloxy)-N-benzylphenylacetamide 在 三乙胺 作用下， 以 乙腈 为溶剂， 以72%的产率得到N-benzyl-2-methoxy-2-phenylacetamide
  参考文献：
  名称：

  Preparation of .alpha.-Alkoxy Amides and .alpha.-Hydrazino Amides by Base-Promoted Reactions of N-Sulfonyloxy Amides

  摘要：

  DOI：

  10.1021/jo00126a072

文献信息

• Simple Synthesis of Amides and Weinreb Amides Using PPh3 or Polymer-Supported PPh3 and Iodine
  作者：Amit Kumar、Hari Kiran Akula、Mahesh K. Lakshman

  DOI：10.1002/ejoc.200901420

  日期：2010.5

  range of carboxylic acids to 2 degrees , 3 degrees , and Weinreb amides. Simplification of the procedure was possible with the use of polymer-supported PPh3/I2. Weinreb amides produced via the use of polymer-supported PPh3 could be filtered through a short silica gel plug and used in further transformations. Thus, use of polymer-supported PPh3 offers potential applicability to diversity-oriented reactions

  已经证明，PPh 3 / I 2的组合对于将一系列羧酸转化为2度，3度和Weinreb酰胺是有效的。使用聚合物负载的PPh3 / I2可以简化程序。通过使用聚合物负载的PPh3制备的Weinreb酰胺可以通过短硅胶塞过滤，并用于进一步的转化。因此，使用聚合物负载的PPh3可为面向多样性的反应提供潜在的适用性。通过使用这种酰胺形成方法，已经完成了载脂蛋白和普拉托恩的正式全部合成，以及脱水胆碱酮和马来帕定的合成。已尝试获得对该反应的了解。
• New boron(III)-catalyzed amide and ester condensation reactions
  作者：Toshikatsu Maki、Kazuaki Ishihara、Hisashi Yamamoto

  DOI：10.1016/j.tet.2007.03.157

  日期：2007.8

  meta- or para-position are highly effective catalysts for the amide condensation reaction in less-polar solvents. In this paper, we report that N-alkyl-4-boronopyridinium halides are more effective catalysts than the previous ones in more polar solvents. N-Alkyl-4-boronopyridinium halides are effective not only for amide condensation between equimolar mixtures of carboxylic acids and amines but also

  1996年，我们报道了在间位或对位带有吸电子基团的苯硼酸是在极性较小的溶剂中进行酰胺缩合反应的高效催化剂。在本文中，我们报告了在极性更大的溶剂中，N-烷基-4-硼吡啶鎓卤化物比以前的催化剂更有效。ñ-烷基-4-硼烷基吡啶鎓卤化物不仅对于羧酸和胺的等摩尔混合物之间的酰胺缩合有效，而且对于在醇溶剂中α-羟基羧酸的酯化都是有效的。此外，对于空间上需要的羧酸的酰胺缩合，全氯儿茶酚硼烷比芳烃硼酸更有效。此外，路易斯酸辅助的布朗斯台德酸（LBA）由硼酸和四氯邻苯二酚的1：2 M混合物制得，对从醇和腈到酰胺的Ritter反应有效。
• <i>N</i>-Alkyl-4-boronopyridinium Salts as Thermally Stable and Reusable Amide Condensation Catalysts
  作者：Toshikatsu Maki、Kazuaki Ishihara、Hisashi Yamamoto

  DOI：10.1021/ol052060l

  日期：2005.10.1

  N-Alkyl-4-boronopyridinium salts are highly effective and reusable catalysts for the dehydrative amide condensation reaction between equimolar mixtures of carboxylic acids and amines. N-Alkylboronopyridinium salts are thermally stabilized in the order N-alkyl-2-boronopyridinium salt << N-alkyl-3-boronopyridinium salt < N-alkyl-4-boronopyridinium salt. Homogeneous catalysts, such as 4-borono-N-methylpyridinium

  [反应：见正文] N-烷基-4-硼基吡啶鎓盐是用于羧酸和胺等摩尔混合物之间的脱水酰胺缩合反应的高效且可重复使用的催化剂。N-烷基硼基吡啶鎓盐按N-烷基-2-硼基吡啶鎓盐<< N-烷基-3-硼基吡啶鎓盐
• The anticonvulsant activities of functionalized N-benzyl 2-acetamidoacetamides. The importance of the 2-acetamido substituent
  作者：Daeock Choi、James P Stables、Harold Kohn

  DOI：10.1016/s0968-0896(96)00225-8

  日期：1996.12

  Recent studies have demonstrated that substituted N-benzyl 2-acetamidoacetamides provide significant protection against maximal electroshock (MES)-induced seizures in mice and rats. In this study, we investigated whether the 2-acetamido moiety was necessary for anticonvulsant activity. Ten derivatives of the known anticonvulsant, N-benzyl 2-acetamido-2-phenyl acetamide were prepared in which the 2-acetamido group was replaced by hydrogen, methyl, oxygen, and halogen substituents. Evaluation of these compounds in the MES-induced seizure test demonstrated that both the hydroxy and the methoxy compounds provided full protection against MES-induced seizures in mice given ip at 100 mg/kg. Moreover, evaluation of the individual stereoisomers for the hydroxy compound showed that the principal activity resided in the (R)-isomer. These findings demonstrated that the 2-acetamido substituent is important but not obligatory for the prevention of MES-induced seizures. Further supporting evidence was provided by comparing the pharmacological activities of N-benzyl 2,3-dimethoxypropionamide with N-benzyl 2-acetamido-3-methoxypropionamide. The ED(50) value for the former in the MES test was 30 mg/kg (ip), which compared favorably with phenobarbital (ED(50) = 22 mg/kg), but the ED(50) value for N-benzyl 2-acetamido-3-methoxypropionamide was 8.3 mg/kg. Copyright (C) 1996 Elsevier Science Ltd
• IRIUCHIJIMA SHINOBU; MANIWA KEIKO; TSUCHINASHI GEN-ICHI, AGR. AND BIOL. CHEM., 1976, 40, NO 12, 2389-2396
  作者：IRIUCHIJIMA SHINOBU、 MANIWA KEIKO、 TSUCHINASHI GEN-ICHI

  DOI：——

  日期：——