4-[N-acetyl-N-(2-iodophenyl)amino]cyclohexanone | 369387-34-8

• 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: 4-[N-acetyl-N-(2-iodophenyl)amino]cyclohexanone
• 英文别名: N-(2-Iodophenyl)-N-(4-oxocyclohexyl)acetamide；N-(2-iodophenyl)-N-(4-oxocyclohexyl)acetamide
• CAS: 369387-34-8
• 化学式: C₁₄H₁₆INO₂
• 分子量: 357.191
• InChiKey: MQOUGFLRVCEHSX-UHFFFAOYSA-N

物化性质

• 沸点：
  459.7±40.0 °C(Predicted)
• 密度：
  1.608±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-[N-acetyl-N-(2-iodophenyl)amino]cyclohexanone 在 四(三苯基膦)钯 potassium phosphate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以38%的产率得到1-acetyl-2,3,4,6-tetrahydro-2,6-methano-1H-1-benzazocin-5-one
  参考文献：
  名称：

  钯催化的芳基卤化物和酮烯酸酯的分子内偶联：六氢-2,6-甲氧基-1-2的合成

  摘要：

  钯催化的2-卤代苯胺和酮烯醇酸酯的分子内偶联是合成六氢-2,6-甲基-1-2衍生物的有用方法。报道了关于该方法的反应条件的研究。

  DOI：

  10.1002/1615-4169(200107)343:5<439::aid-adsc439>3.0.co;2-g
• 作为产物：
  描述：

  1,4-环己二酮单乙二醇缩酮 在 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 135.0h， 生成 4-[N-acetyl-N-(2-iodophenyl)amino]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

文献信息

• Palladium-Catalyzed Intramolecular Coupling of Aryl Halides and Ketone Enolates: Synthesis of Hexahydro-2,6-methano-1-benzazocines
  作者：Daniel Solé、Lluís Vallverdú、Josep Bonjoch

  DOI：10.1002/1615-4169(200107)343:5<439::aid-adsc439>3.0.co;2-g

  日期：2001.7

  The palladium-catalyzed intramolecular coupling of 2-haloanilines and ketone enolates is a useful methodology for the synthesis of hexahydro-2,6-methano-1-2 derivatives. A study about the reaction conditions of the process is reported.

  钯催化的2-卤代苯胺和酮烯醇酸酯的分子内偶联是合成六氢-2,6-甲基-1-2衍生物的有用方法。报道了关于该方法的反应条件的研究。
• 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
  作者：Daniel Solé、Lluís Vallverdú、Xavier Solans、Mercè Font-Bardía、Josep Bonjoch

  DOI：10.1021/ja029114w

  日期：2003.2.1

  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.