(S)-3-bromo-N-(1-phenylethyl)benzamide | 1075255-78-5

• 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: (S)-3-bromo-N-(1-phenylethyl)benzamide
• 英文别名: 3-bromo-N-[(1S)-1-phenylethyl]benzamide
• CAS: 1075255-78-5
• 化学式: C₁₅H₁₄BrNO
• 分子量: 304.186
• InChiKey: HMYKUFFNKSBISJ-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (S)-3-bromo-N-(1-phenylethyl)benzamide 、 三甲基乙炔基硅 在 copper(l) iodide 、 三乙胺 、 三苯基膦 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 (S)-N-(1-phenylethyl)-3-((trimethylsilyl)ethynyl)benzamide
  参考文献：
  名称：

  Biased Helical Folding of Chiral Oligoindole Foldamers

  摘要：

  Oligoindole-based chiral foldamers have been synthesized by incorporating (S)- or (R)-1-phenylethylamine to both ends of the tetraindole scaffold. The oligoindoles fold into a helical conformation upon binding an anion by hydrogen bonds, which gives rise to an induced circular dichroism (CD) signal of large amplitude, implying the preferential formation of one helical isomer over another. Theoretical calculations suggest that the (P)-helix of the (SS)-oligoindole 8a be more energetically stable than the corresponding (M)-helix.

  DOI：

  10.1021/ol8022243
• 作为产物：
  描述：

  3-溴苯甲酰氯 、 (S)-(-)- α-甲基苄胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以92%的产率得到(S)-3-bromo-N-(1-phenylethyl)benzamide
  参考文献：
  名称：

  Biased Helical Folding of Chiral Oligoindole Foldamers

  摘要：

  Oligoindole-based chiral foldamers have been synthesized by incorporating (S)- or (R)-1-phenylethylamine to both ends of the tetraindole scaffold. The oligoindoles fold into a helical conformation upon binding an anion by hydrogen bonds, which gives rise to an induced circular dichroism (CD) signal of large amplitude, implying the preferential formation of one helical isomer over another. Theoretical calculations suggest that the (P)-helix of the (SS)-oligoindole 8a be more energetically stable than the corresponding (M)-helix.

  DOI：

  10.1021/ol8022243

文献信息

• Superparamagnetic Fe(OH)₃@Fe₃O₄ Nanoparticles: An Efficient and Recoverable Catalyst for Tandem Oxidative Amidation of Alcohols with Amine Hydrochloride Salts
  作者：Marzban Arefi、Dariush Saberi、Meghdad Karimi、Akbar Heydari

  DOI：10.1021/co5001844

  日期：2015.6.8

  nanoparticles were successfully prepared and characterized. This magnetic nanocomposite was employed as an efficient, reusable, and environmentally benign heterogeneous catalyst for the direct amidation of alcohols with amine hydrochloride salts. Several derivatives of primary, secondary and tertiary amides were synthesized in moderate to good yields in the presence of this catalytic system. The catalyst was

  磁性Fe（OH）3 @Fe 3 O 4纳米粒子的制备和表征成功。该磁性纳米复合材料用作将醇与胺盐酸盐直接酰胺化的有效，可重复使用且对环境无害的多相催化剂。在该催化体系的存在下，以中等至良好的产率合成了伯，仲和叔酰胺的几种衍生物。该催化剂已成功回收利用，最多可重复使用六次，而不会显着降低其催化活性。
• CuH‐Catalyzed Asymmetric Hydroamidation of Vinylarenes
  作者：Yujing Zhou、Oliver D. Engl、Jeffrey S. Bandar、Emma D. Chant、Stephen L. Buchwald

  DOI：10.1002/anie.201802797

  日期：2018.5.28

  A CuH‐catalyzed enantioselective hydroamidation reaction of vinylarenes has been developed using readily accessible 1,4,2‐dioxazol‐5‐ones as electrophilic amidating reagents. This method provides a straightforward and efficient approach to synthesize chiral amides in good yields with high levels of enantiopurity under mild conditions. Moreover, this transformation tolerates substrates bearing a broad

  使用容易获得的1,4,2-二恶唑-5-酮作为亲电子酰胺化试剂，开发了CuH催化的乙烯基芳烃对映选择性加氢酰胺化反应。该方法提供了一种简单有效的方法，可以在温和条件下以高收率和高对映体纯度合成手性酰胺。而且，这种转变可耐受带有广泛官能团的底物。