2-[N-(2-iodophenyl)aminomethyl]cyclohexanone | 501346-81-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-[N-(2-iodophenyl)aminomethyl]cyclohexanone
• 英文别名: 2-[(2-Iodoanilino)methyl]cyclohexan-1-one
• CAS: 501346-81-2
• 化学式: C₁₃H₁₆INO
• 分子量: 329.181
• InChiKey: ZIIDWNLWTAJGHI-UHFFFAOYSA-N

物化性质

• 沸点：
  417.9±20.0 °C(Predicted)
• 密度：
  1.567±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[N-(2-iodophenyl)aminomethyl]cyclohexanone 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 caesium carbonate 、 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 84.0h， 生成 cis-5-methyl-5,6,6a,7,8,9,10,10a-octahydro-10a-phenanthridinol
  参考文献：
  名称：

  Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles

  摘要：

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.

  DOI：

  10.1021/ja029114w
• 作为产物：
  描述：

  2-碘苯胺 在 三氟化硼乙醚 、 碳酸氢钠 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 81.0h， 生成 2-[N-(2-iodophenyl)aminomethyl]cyclohexanone
  参考文献：
  名称：

  Intramolecular Pd-Mediated Processes of Amino-Tethered Aryl Halides and Ketones:  Insight into the Ketone α-Arylation and Carbonyl-Addition Dichotomy. A New Class of Four-Membered Azapalladacycles

  摘要：

  An exploration of the scope and limitations of Pd(0)-catalyzed intramolecular coupling reactions of amino-tethered aryl halides and ketones has been conducted. Two different and competitive reaction pathways starting from omega-(2-haloanilino) alkanones, enolate arylation and addition to the carbonyl group, have been observed, while (omega-(2-halobenzylamino) alkanones exclusively underwent the enolate arylation process. The dichotomy between ketone alpha-arylation and carbonyl-addition in the reactions of omega-(2-haloanilino) alkanones has been rationalized by the intermediacy of unprecedented four-membered azapalladacycles, from which X-ray data and chemical behavior are reported.

  DOI：

  10.1021/ja029114w