N-(2-phenylethyl)-9H-fluorene-9-carboxamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(2-phenylethyl)-9H-fluorene-9-carboxamide
• 化学式: C₂₂H₁₉NO
• 分子量: 313.399
• InChiKey: XOOBEYDFZRCLSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二溴二氟甲烷 、 fluorenone N-phenethylimine 在 lead 、 四丁基溴化铵 、 水 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 70.0h， 以2%的产率得到N-(2-phenylethyl)-9H-fluorene-9-carboxamide
  参考文献：
  名称：

  Regioselectivity of the 1,3-dipolar cycloaddition of fluorinated fluoren-9-iminium ylides to heteroelement-containing dipolarophiles: Experimental and quantum-chemical study

  摘要：

  N-Substituted 9H-fluoren-9-imines react with difluorocarbene to give the corresponding iminium ylides whose further transformations in the absence of active dipolarophiles depend on the substituent at the nitrogen atom and reaction conditions. N-Ethyl-, N-benzyl-, and N-(2-phenylethyl)-9H-fluoren-9-imines are thus converted in low yield into the formal cyclodimerization products and/or 9H-fluorene-9-carboxamides. N-Methyl-substituted fluoreniminium ylide readily adds at the C=N bond of initial N-(9H-fluoren-9-ylidene)methanamine with formation of spiro-fused imidazolidine derivative; in the presence of fluorenone, acetaldehyde, or benzaldehyde, addition at the C=O group of the dipolarophile occurs to give the corresponding oxazolidine derivatives. The regioselectivity of the cycloaddition of iminium ylides having a fluorene fragment at a double carbon-heteroelement bond can be described by quantum-chemical calculations in terms of the density functional theory (DFT; local hard and soft acids and bases concept): the cycloaddition leads preferentially to the 2,2-difluoro-substituted adduct.

  DOI：

  10.1134/s1070428006120086

文献信息

• Regioselectivity of the 1,3-dipolar cycloaddition of fluorinated fluoren-9-iminium ylides to heteroelement-containing dipolarophiles: Experimental and quantum-chemical study
  作者：M. S. Novikov、A. F. Khlebnikov、M. A. Egarmin、M. V. Shevchenko、V. A. Khlebnikov、R. R. Kostikov、D. Vidovic

  DOI：10.1134/s1070428006120086

  日期：2006.12

  N-Substituted 9H-fluoren-9-imines react with difluorocarbene to give the corresponding iminium ylides whose further transformations in the absence of active dipolarophiles depend on the substituent at the nitrogen atom and reaction conditions. N-Ethyl-, N-benzyl-, and N-(2-phenylethyl)-9H-fluoren-9-imines are thus converted in low yield into the formal cyclodimerization products and/or 9H-fluorene-9-carboxamides. N-Methyl-substituted fluoreniminium ylide readily adds at the C=N bond of initial N-(9H-fluoren-9-ylidene)methanamine with formation of spiro-fused imidazolidine derivative; in the presence of fluorenone, acetaldehyde, or benzaldehyde, addition at the C=O group of the dipolarophile occurs to give the corresponding oxazolidine derivatives. The regioselectivity of the cycloaddition of iminium ylides having a fluorene fragment at a double carbon-heteroelement bond can be described by quantum-chemical calculations in terms of the density functional theory (DFT; local hard and soft acids and bases concept): the cycloaddition leads preferentially to the 2,2-difluoro-substituted adduct.