N,N-二异丙基-2-(3-氨基-2-氯-4-吡啶基)苯甲酰胺 | 153035-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: N,N-二异丙基-2-(3-氨基-2-氯-4-吡啶基)苯甲酰胺
• 英文名称: N,N-Diisopropyl-2-(3-amino-2-chloro-4-pyridyl)benzamide
• 英文别名: 2-(3-amino-2-chloropyridin-4-yl)-N,N-di(propan-2-yl)benzamide
• CAS: 153035-13-3
• 化学式: C₁₈H₂₂ClN₃O
• 分子量: 331.845
• InChiKey: YGTZJCJJUJMEQJ-UHFFFAOYSA-N

物化性质

• 沸点：
  504.4±50.0 °C(predicted)
• 密度：
  1.167±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N,N-二异丙基-2-(3-氨基-2-氯-4-吡啶基)苯甲酰胺 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 以82%的产率得到1-Chloro-2,10-diazaphenanthren-9(10H)-one
  参考文献：
  名称：

  First metalation of aryl iodides: directed ortho-lithiation of iodopyridines, halogen-dance, and application to synthesis

  摘要：

  Metalation of iodopyridines was successfully achieved by LDA at low temperature. In many cases, lithiation is ortho directed by the iodo group which subsequently ortho-migrates very fast to give stabilized iodolithiopyridines. This procedure was applied to 2-fluoro-and 2-chloro-3-iodopyridines, 3-fluoro-4-iodopyridine, and 2-chloro-3-fluoro-4-iodopyridine. The resulting lithio intermediates were obtained in high yields before being reacted with electrophiles leading to various polysubstituted pyridines. Some of these iodopyridines were used as key molecules for the synthesis of fused polyaromatic alkaloids. Thus, perlolidine, delta-carbolines, and 2,10-diazaphenanthrenes were readily prepared in few steps taking advantage of the iodo reactivity for heteroring cross-coupling.

  DOI：

  10.1021/jo00079a031
• 作为产物：
  描述：

  3-叠氮基-2-氯-4-碘吡啶 在 四(三苯基膦)钯 哌啶 、 硫化氢 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 25.0h， 生成 N,N-二异丙基-2-(3-氨基-2-氯-4-吡啶基)苯甲酰胺
  参考文献：
  名称：

  First metalation of aryl iodides: directed ortho-lithiation of iodopyridines, halogen-dance, and application to synthesis

  摘要：

  Metalation of iodopyridines was successfully achieved by LDA at low temperature. In many cases, lithiation is ortho directed by the iodo group which subsequently ortho-migrates very fast to give stabilized iodolithiopyridines. This procedure was applied to 2-fluoro-and 2-chloro-3-iodopyridines, 3-fluoro-4-iodopyridine, and 2-chloro-3-fluoro-4-iodopyridine. The resulting lithio intermediates were obtained in high yields before being reacted with electrophiles leading to various polysubstituted pyridines. Some of these iodopyridines were used as key molecules for the synthesis of fused polyaromatic alkaloids. Thus, perlolidine, delta-carbolines, and 2,10-diazaphenanthrenes were readily prepared in few steps taking advantage of the iodo reactivity for heteroring cross-coupling.

  DOI：

  10.1021/jo00079a031

文献信息

• First metalation of aryl iodides: directed ortho-lithiation of iodopyridines, halogen-dance, and application to synthesis
  作者：P. Rocca、C. Cochennec、F. Marsais、L. Thomas-dit-Dumont、M. Mallet、A. Godard、G. Queguiner

  DOI：10.1021/jo00079a031

  日期：1993.12

  Metalation of iodopyridines was successfully achieved by LDA at low temperature. In many cases, lithiation is ortho directed by the iodo group which subsequently ortho-migrates very fast to give stabilized iodolithiopyridines. This procedure was applied to 2-fluoro-and 2-chloro-3-iodopyridines, 3-fluoro-4-iodopyridine, and 2-chloro-3-fluoro-4-iodopyridine. The resulting lithio intermediates were obtained in high yields before being reacted with electrophiles leading to various polysubstituted pyridines. Some of these iodopyridines were used as key molecules for the synthesis of fused polyaromatic alkaloids. Thus, perlolidine, delta-carbolines, and 2,10-diazaphenanthrenes were readily prepared in few steps taking advantage of the iodo reactivity for heteroring cross-coupling.