N-(2,4-Diiodo-5-methylphenyl)-2,2,2-trifluoroacetamide | 919771-65-6

• 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-(2,4-Diiodo-5-methylphenyl)-2,2,2-trifluoroacetamide
• 英文别名: N-(2,4-diiodo-5-methylphenyl)-2,2,2-trifluoroacetamide
• CAS: 919771-65-6
• 化学式: C₉H₆F₃I₂NO
• 分子量: 454.957
• InChiKey: NEPYCDKGIQWWMV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2,4-Diiodo-5-methylphenyl)-2,2,2-trifluoroacetamide 、 异丁酰醋酸甲酯 在 copper(l) iodide 、 caesium carbonate 、 L-脯氨酸 作用下， 以 二甲基亚砜 为溶剂， 反应 15.0h， 以79%的产率得到methyl 5-iodo-6-methyl-2-(trifluoromethyl)-1H-indole-3-carboxylate
  参考文献：
  名称：

  Elaboration of 2-(Trifluoromethyl)indoles via a Cascade Coupling/Condensation/Deacylation Process

  摘要：

  Cul/L-proline-catalyzed coupling of 2-halotrifluoroacetanilides with beta-keto esters in anhydrous DMSO under the action Of Cs2CO3 at 40-80 degrees C produces polysubstituted 2-(trifluoromethyl)indoles in good to excellent yields. This reaction is suggested to occur via a novel coupling/condensation/deacylation mechanism, and many functional groups are tolerated under these conditions.

  DOI：

  10.1021/ol7029382

文献信息

• Enantioselective Arylation of 2-Methylacetoacetates Catalyzed by CuI/<i>trans</i>-4-Hydroxy-<scp>l</scp>-proline at Low Reaction Temperatures
  作者：Xiaoan Xie、Yu Chen、Dawei Ma

  DOI：10.1021/ja066991j

  日期：2006.12.1

  CuI/trans-4-hydroxy-l-proline-catalyzed coupling reaction of 2-iodotrifluoroacetanilides with 2-methylacetoacetates took place at -45 degrees C to create alpha-aryl all-carbon quaternary centers enantioselectively. Up to 93% ee was achieved when tert-butyl ester was used. The combination of ligand, ortho substituent (participation of NHCOCF3), and solvent effects was shown to account for these unprecedentedly mild reaction conditions.
• Elaboration of 2-(Trifluoromethyl)indoles via a Cascade Coupling/Condensation/Deacylation Process
  作者：Yu Chen、Yuji Wang、Zheming Sun、Dawei Ma

  DOI：10.1021/ol7029382

  日期：2008.2.1

  Cul/L-proline-catalyzed coupling of 2-halotrifluoroacetanilides with beta-keto esters in anhydrous DMSO under the action Of Cs2CO3 at 40-80 degrees C produces polysubstituted 2-(trifluoromethyl)indoles in good to excellent yields. This reaction is suggested to occur via a novel coupling/condensation/deacylation mechanism, and many functional groups are tolerated under these conditions.