2,2-dichloro-N-(naphthalen-1-yl)acetamide | 1140-53-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2,2-dichloro-N-(naphthalen-1-yl)acetamide
• 英文别名: 2,2-dichloro-N-(1-naphthyl)acetamide；2,2-dichloro-N-naphthalen-1-ylacetamide
• CAS: 1140-53-0
• 化学式: C₁₂H₉Cl₂NO
• 分子量: 254.116
• InChiKey: SJVSQQFAACIPOJ-UHFFFAOYSA-N

物化性质

• 保留指数：
  2035

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 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：

  二氯甲烷 、 1-Alapha-萘异氰酸酯 在 2,2,6,6-四甲基哌啶 、 甲基锂 、 lithium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以85%的产率得到2,2-dichloro-N-(naphthalen-1-yl)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

• Dichloromeldrum’s Acid (DiCMA): A Practical and Green Amine Dichloroacetylation Reagent
  作者：David M. Heard、Alastair J. J. Lennox

  DOI：10.1021/acs.orglett.1c00850

  日期：2021.5.7

  dichloroacetylation of anilines and alkyl amines to produce α,α-dichloroacetamides, which are important motifs for medicinal chemistry. Products are formed in good to excellent yields with reagent grade solvents, and, as the only byproducts are acetone and CO2, no column chromatography is required. Thus, this reagent is practical, efficient, and green for the dichloroacetylation of primary amines.

  引入二氯甲mel酸是一种稳定的，不挥发的试剂，用于苯胺和烷基胺的二氯乙酰化，以生产α，α-二氯乙酰胺，这是药物化学的重要主题。使用试剂级溶剂可形成高至极佳收率的产物，并且由于唯一的副产物是丙酮和CO 2，因此无需柱色谱法。因此，该试剂对于伯胺的二氯乙酰化是实用，有效和绿色的。