3-chloro-N-(2-methoxyphenyl)-2-methylaniline | 1369183-65-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-chloro-N-(2-methoxyphenyl)-2-methylaniline
• CAS: 1369183-65-2
• 化学式: C₁₄H₁₄ClNO
• 分子量: 247.724
• InChiKey: OLFVLSPIQHMHFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-N-(2-methoxyphenyl)-2-methylaniline 在 copper diacetate 、 palladium diacetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 以70%的产率得到2-chloro-8-methoxy-1-methyl-9H-carbazole
  参考文献：
  名称：

  Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

  摘要：

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

  DOI：

  10.1055/s-0032-1317175
• 作为产物：
  描述：

  3-氯-2-甲基苯胺 在 palladium diacetate 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 38.0h， 生成 3-chloro-N-(2-methoxyphenyl)-2-methylaniline
  参考文献：
  名称：

  Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids

  摘要：

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.

  DOI：

  10.1055/s-0032-1317175

文献信息

• Synthetic Approach for Constructing the 1-Oxygenated Carbazole Core and Its Application to the Preparation of Natural Alkaloids
  作者：Joaquín Tamariz、Rafael Bautista、Alberto Jerezano

  DOI：10.1055/s-0032-1317175

  日期：——

  An efficient synthetic approach for the construction of the 1-oxygenated carbazole core is described. The condensation of cyclohexane-1,2-diones with a series of anilines yielded the corresponding 2-anilinocyclohex-2-en-1-ones, followed by the one-pot aromatization/methylation process of the latter to provide N-aryl-2-methoxyanilines. A palladium(II)-catalyzed cyclization of these N-aryl-2-methoxyanilines afforded the desired 1-methoxycarbazole frame in high overall yields. This protocol was implemented for the total synthesis of the naturally occurring glycozolicine and 6-methoxymurrayanine.