2,2-dichloro-N-(3-phenylpropyl)acetamide | 104413-34-5

• 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: 2,2-dichloro-N-(3-phenylpropyl)acetamide
• 英文别名: dichloro-acetic acid-(3-phenyl-propylamide)；Dichlor-essigsaeure-(3-phenyl-propylamid)
• CAS: 104413-34-5
• 化学式: C₁₁H₁₃Cl₂NO
• 分子量: 246.136
• InChiKey: NFRHHUVLPRPCQF-UHFFFAOYSA-N

物化性质

• 沸点：
  392.6±42.0 °C(Predicted)
• 密度：
  1.225±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  15
• 可旋转键数：
  5
• 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：

  2,2-dichloro-N-(3-phenylpropyl)acetamide 在 二氯乙酸 、 乙酸酐 、 sodium nitrite 作用下， 反应 6.5h， 生成
  参考文献：
  名称：

  Using N-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols

  摘要：

  The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.

  DOI：

  10.1080/00397911.2015.1061672
• 作为产物：
  描述：

  二氯乙酸甲酯 、 3-苯基-1-丙胺 以 乙酸乙酯 为溶剂， 生成 2,2-dichloro-N-(3-phenylpropyl)acetamide
  参考文献：
  名称：

  Using N-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols

  摘要：

  The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.

  DOI：

  10.1080/00397911.2015.1061672

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。
• Chloromycetin (Chloramphenicol¹). Related Compounds Having Alkyl Side Chain Variations
  作者：Mildred C. Rebstock、George W. Moersch、Allen C. Moore、J. M. Vandenbelt

  DOI：10.1021/ja01152a030

  日期：1951.8
• Using <i>N</i>-Nitrosodichloroacetamides to Conveniently Convert Linear Primary Amines into Alcohols
  作者：Nicholas S. MacArthur、Linshu Wang、Blaine G. McCarthy、Charles E. Jakobsche

  DOI：10.1080/00397911.2015.1061672

  日期：2015.9.2

  The reported rearrangement of N-nitrosodichloroacetamides provides a practicalmethod for converting primary amines into primary alcohols. The reaction sequence is operationally simple, requires only a single purification, and is compatible with a number of common functional groups. Mechanistic studies of the nitrosylation and rearrangement reactions illustrate the increased utility of dichloroacetamides compared to various other amides for this transformation.