N-benzyl-2,3-dichlorobenzamide | 428451-78-9

• 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: N-benzyl-2,3-dichlorobenzamide
• 英文别名: Cambridge id 6397361
• CAS: 428451-78-9
• 化学式: C₁₄H₁₁Cl₂NO
• mdl: MFCD02917493
• 分子量: 280.153
• InChiKey: NOBRGQYHMUFXPC-UHFFFAOYSA-N

物化性质

• 沸点：
  415.1±45.0 °C(Predicted)
• 密度：
  1.306±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 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：

  2,5-降冰片二烯 、 N-benzyl-2,3-dichlorobenzamide 在 palladium diacetate 、 caesium carbonate 、 三苯基膦 作用下， 以 甲苯 为溶剂， 以35%的产率得到2-benzyl-5-chloroisoquinolin-1(2H)-one
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles

  摘要：

  A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.

  DOI：

  10.1021/jo802604g
• 作为产物：
  描述：

  2,3-二氯苯甲酸 、 苄胺 在 1,2-二氯乙烷 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 以44%的产率得到N-benzyl-2,3-dichlorobenzamide
  参考文献：
  名称：

  Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles

  摘要：

  A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.

  DOI：

  10.1021/jo802604g

文献信息

• A useful acylation method using trichloroacetonitrile and triphenylphosphine for solid phase organic synthesis
  作者：István Vágó、István Greiner

  DOI：10.1016/s0040-4039(02)01241-8

  日期：2002.8

  A novel acylation procedure was developed for polymer supported synthesis, with in situ generated acyl chlorides using trichloroacetonitrile and triphenylphosphine.

  开发了一种新的酰化方法，用于聚合物支持的合成，使用三氯乙腈和三苯基膦原位生成的酰氯。
• Palladium-Catalyzed Annulation of Haloanilines and Halobenzamides Using Norbornadiene as an Acetylene Synthon: A Route to Functionalized Indolines, Isoquinolinones, and Indoles
  作者：Praew Thansandote、David G. Hulcoop、Michael Langer、Mark Lautens

  DOI：10.1021/jo802604g

  日期：2009.2.20

  A general procedure for the palladium-catalyzed annulation of substituted haloanilines with norbornadiene gives functionalized indolines in 51-98% yield. These indolines can be rapidly converted to benzenoid-substituted indoles and tricyclic indolines. Extension to the use of substituted halobenzamides gives functionalized isoquinolinones in up to 86% yield.