2-iodo-N-(1-phenylethyl)acetamide | 868255-01-0

• 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-iodo-N-(1-phenylethyl)acetamide
• CAS: 868255-01-0
• 化学式: C₁₀H₁₂INO
• 分子量: 289.116
• InChiKey: FGQFQEPWENBEJW-UHFFFAOYSA-N

物化性质

• 沸点：
  394.2±35.0 °C(Predicted)
• 密度：
  1.599±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二碘甲烷 、 alpha-甲基异氰酸苄酯 在 甲基锂 、 lithium bromide 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以98%的产率得到2-iodo-N-(1-phenylethyl)acetamide
  参考文献：
  名称：

  Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides

  摘要：

  Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of -halo- and ,-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal. The clear advantages of the procedure are: (a) broad scope of isocyanates that can be employed; (b) preservation of the optical purity when chiral materials are used; (c) divergent access to different haloamides by simply selecting the homologating agents. We also report an application of Charette's imidoyl triflate activation of a secondary amide to the synthesis of an -chloro ketone and N-15 NMR data for selected compounds.

  DOI：

  10.1055/s-0034-1379209

文献信息

• Addition of lithium carbenoids to isocyanates: a direct access to synthetically useful N-substituted 2-haloacetamides
  作者：Vittorio Pace、Laura Castoldi、Wolfgang Holzer

  DOI：10.1039/c3cc44255a

  日期：——

  presence of variously functionalized substituents on the nitrogen atom, including sterically demanding ones and reactive halogens. No erosion of the enantiopurity was observed in the case of optically active isocyanates. One of the substrates prepared has been employed in Charette's type chemoselective addition of a Grignard reagent to access an alpha-chloroketone.

  向异氰酸酯中添加类胡萝卜酸锂可提供N-取代的2-卤代乙酰胺的通用途径：该反应可耐受氮原子上存在各种官能化的取代基，包括空间上需要的取代基和反应性卤素。在光学活性异氰酸酯的情况下，未观察到对映体纯度的侵蚀。所制备的底物之一已用于格氏试剂的Charette型化学选择性添加中，从而获得α-氯酮。
• METHOD AND COMPOSITIONS FOR THE TREATMENT OF ANEMIA THROUGH THE INHIBITION OF FURIN
  申请人：BRIGHAM YOUNG UNIVERSITY

  公开号：US20210186992A1

  公开（公告）日：2021-06-24

  Methods and compositions that can be used to modulate the activity of furin in a subject are disclosed herein. In some embodiments, the methods include administering a pharmaceutical composition including a protease inhibitor. In some embodiments, the protease inhibitor inhibits furin activity by binding to the catalytic site, the allosteric site, or both.
• [EN] METHOD AND COMPOSITIONS FOR THE TREATMENT OF ANEMIA THROUGH THE INHIBITION OF FURIN<br/>[FR] MÉTHODE ET COMPOSITIONS POUR LE TRAITEMENT DE L'ANÉMIE PAR INHIBITION DE FURINE
  申请人：UNIV BRIGHAM YOUNG

  公开号：WO2017147078A1

  公开（公告）日：2017-08-31

  Methods and compositions that can be used to modulate the activity of furin in a subject are disclosed herein. In some embodiments, the methods include administering a pharmaceutical composition including a protease inhibitor. In some embodiments, the protease inhibitor inhibits furin activity by binding to the catalytic site, the allosteric site, or both.
• Homologation of Isocyanates with Lithium Carbenoids: A Straightforward Access to α-Halomethyl- and α,α-Dihalomethylamides
  作者：Vittorio Pace、Laura Castoldi、Ashenafi Mamuye、Wolfgang Holzer

  DOI：10.1055/s-0034-1379209

  日期：——

  Treatment of widely available isocyanates with monohalolithium and dihalolithium carbenoids provides a valuable protocol for the one-pot preparation of -halo- and ,-dihaloacetamide derivatives. While monohalolithium carbenoids can be prepared by a smooth lithium-halogen exchange, the preparation of the corresponding dihalo compounds proved to be highly dependent on the base used to realize the deprotonation, with lithium 2,2,6,6-tetramethylpiperidine emerging as optimal. The clear advantages of the procedure are: (a) broad scope of isocyanates that can be employed; (b) preservation of the optical purity when chiral materials are used; (c) divergent access to different haloamides by simply selecting the homologating agents. We also report an application of Charette's imidoyl triflate activation of a secondary amide to the synthesis of an -chloro ketone and N-15 NMR data for selected compounds.