2-bromo-N-(1-phenylethyl)propionamide | 25027-38-7

• 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: 2-bromo-N-(1-phenylethyl)propionamide
• 英文别名: N-(α-Methylbenzyl)-2-brompropionamid；2-bromo-N-(1-phenylethyl)propanamide
• CAS: 25027-38-7
• 化学式: C₁₁H₁₄BrNO
• 分子量: 256.142
• InChiKey: QYAAFAXOBIYBIR-UHFFFAOYSA-N

物化性质

• 沸点：
  376.8±35.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 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：

  2-bromo-N-(1-phenylethyl)propionamide 在 过氯酰氟 、 sodium iodide 、 lithium diisopropyl amide 作用下， 反应 24.5h， 生成 2-cyano-2-fluoro-N-(1-phenylethyl)propionamide
  参考文献：
  名称：

  Chemistry of novel compounds with multifunctional carbon structure. 9. Molecular design, synthetic studies, and NMR investigation of several efficient chiral derivatizing reagents which give very large 19F NMR .DELTA..delta. values in enantiomeric excess determination

  摘要：

  In order to develop efficient ee-determining reagents potentially superior to MTPA (1), some multifunctional compounds 2-5 were rationally designed. From NMR investigations of the analogous diastereomeric derivatives it was found that the chemical shift differences for each pair of diastereomers (DELTAdelta values) for CFPA derivatives 5d-f were approximately five times greater in F-19 NMR spectra and two times greater in H-1 NMR spectra than those of 1d-f. Synthesis of the optically pure CFPA, (-)-5a and (+)-5a, was achieved by nitrosation of each diastereomer of the optically active N-(1-phenylethyl)amides, 5f(M) and 5f(L), followed by thermal decomposition. Various derivatives were prepared by the condensation of 5b and lb with alcohol and amine nucleophiles, and both DELTAdelta(F) and DELTAdelta(H) Values were obtained for each compound. The CFPA derivatives 5d-m have proven to be significantly superior for ee determinations when compared to the corresponding MTPA derivatives 1d-m, particularly in compounds having remotely disposed chiral centers.

  DOI：

  10.1021/jo00059a036
• 作为产物：
  描述：

  α-苯乙胺 、 2-溴丙酰氯 在 三乙胺 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 2-bromo-N-(1-phenylethyl)propionamide
  参考文献：
  名称：

  Chemistry of novel compounds with multifunctional carbon structure. 9. Molecular design, synthetic studies, and NMR investigation of several efficient chiral derivatizing reagents which give very large 19F NMR .DELTA..delta. values in enantiomeric excess determination

  摘要：

  In order to develop efficient ee-determining reagents potentially superior to MTPA (1), some multifunctional compounds 2-5 were rationally designed. From NMR investigations of the analogous diastereomeric derivatives it was found that the chemical shift differences for each pair of diastereomers (DELTAdelta values) for CFPA derivatives 5d-f were approximately five times greater in F-19 NMR spectra and two times greater in H-1 NMR spectra than those of 1d-f. Synthesis of the optically pure CFPA, (-)-5a and (+)-5a, was achieved by nitrosation of each diastereomer of the optically active N-(1-phenylethyl)amides, 5f(M) and 5f(L), followed by thermal decomposition. Various derivatives were prepared by the condensation of 5b and lb with alcohol and amine nucleophiles, and both DELTAdelta(F) and DELTAdelta(H) Values were obtained for each compound. The CFPA derivatives 5d-m have proven to be significantly superior for ee determinations when compared to the corresponding MTPA derivatives 1d-m, particularly in compounds having remotely disposed chiral centers.

  DOI：

  10.1021/jo00059a036

文献信息

• Design and synthesis of new 8-anilide theophylline derivatives as bronchodilators and antibacterial agents
  作者：Alaa K. M. Hayallah、Ahmad A. Talhouni、Abdel Alim M. Abdel Alim

  DOI：10.1007/s12272-012-0805-4

  日期：2012.8

  Theophylline derivatives have long been recognized as potent bronchodilators for the relief of acute asthma. Recently, it was found that bacterial infection has a role in asthma pathogenesis. The present work involves the design and synthesis of 8-substituted theophylline derivatives as bronchodilators and antibacterial agents. The chemical structures of these compounds were elucidated by IR, 1H-NMR

  长期以来，茶碱衍生物被认为是缓解急性哮喘的有效支气管扩张剂。最近，发现细菌感染在哮喘发病机制中起作用。目前的工作涉及作为支气管扩张剂和抗菌剂的 8-取代茶碱衍生物的设计和合成。这些化合物的化学结构通过IR、1H-NMR、质谱和元素分析阐明。使用乙酰胆碱诱导的豚鼠支气管痉挛评估支气管扩张剂活性，与标准氨茶碱相比，大多数化合物显示出显着的抗支气管收缩活性。此外，使用氨苄青霉素作为参考药物，在体外研究了所有目标化合物对革兰氏阳性菌和革兰氏阴性菌的抗菌活性。结果表明，一些测试化合物具有显着的抗菌活性。计算药效团模型以获得对支气管扩张剂活性的基本结构特征的有用洞察。还讨论了构效关系。
• Cu-Catalyzed C_(sp3)–N Coupling and Alkene Carboamination Enabled by Ligand-Promoted Selective Hydrazine Transfer to Alkyl Radicals
  作者：Dengfu Lu、Yadong Li、Peng Wang、Zijie Wang、Daoyi Yang、Yuefa Gong

  DOI：10.1021/acscatal.2c00250

  日期：2022.3.18

  dinuclear complex with Cu and the ligand which, upon 1e-oxidation, turns into an open-shell species with the major spin density on N atoms. With the assistance of a ligand, this species can selectively deliver the hydrazine moiety onto an alkyl radical (prior to halide transfer), leading to the formation of a C(sp3)–N bond. The products obtained with this amination method could be easily deprotected

  将 N-亲核试剂选择性地传递到烷基自由基上是氧化还原催化中的一个具有挑战性的步骤。在这项工作中，发现二叔丁基叠氮二甲酸酯是铜催化的 C (sp3)中独特的有效胺化试剂-N 键形成反应，涉及烷基自由基中间体。该方法适用于缺电子自由基和富电子自由基，因此我们能够实现活化溴化物的直接C-N偶联，以及基于这种化学的一般烯烃的碳胺化。机理研究表明，二甲酰二甲酸酯与Cu和配体形成还原双核络合物，在1e-氧化后，该配体变成开壳物质，在N原子上具有主要的自旋密度。在配体的帮助下，该物质可以选择性地将肼部分传递到烷基自由基上（在卤化物转移之前），从而形成 C (sp3)-N 键。用这种胺化方法得到的产物可以很容易地脱保护得到烷基肼，并进一步衍生为伯胺或 N-杂环。
• Chemistry of novel compounds with multifunctional carbon structure. 9. Molecular design, synthetic studies, and NMR investigation of several efficient chiral derivatizing reagents which give very large 19F NMR .DELTA..delta. values in enantiomeric excess determination
  作者：Yoshio Takeuchi、Noriaki Itoh、Toshihiro Satoh、Toru Koizumi、Kentaro Yamaguchi

  DOI：10.1021/jo00059a036

  日期：1993.3

  In order to develop efficient ee-determining reagents potentially superior to MTPA (1), some multifunctional compounds 2-5 were rationally designed. From NMR investigations of the analogous diastereomeric derivatives it was found that the chemical shift differences for each pair of diastereomers (DELTAdelta values) for CFPA derivatives 5d-f were approximately five times greater in F-19 NMR spectra and two times greater in H-1 NMR spectra than those of 1d-f. Synthesis of the optically pure CFPA, (-)-5a and (+)-5a, was achieved by nitrosation of each diastereomer of the optically active N-(1-phenylethyl)amides, 5f(M) and 5f(L), followed by thermal decomposition. Various derivatives were prepared by the condensation of 5b and lb with alcohol and amine nucleophiles, and both DELTAdelta(F) and DELTAdelta(H) Values were obtained for each compound. The CFPA derivatives 5d-m have proven to be significantly superior for ee determinations when compared to the corresponding MTPA derivatives 1d-m, particularly in compounds having remotely disposed chiral centers.