fluorenone N-phenethylimine | 119437-41-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: fluorenone N-phenethylimine
• 英文别名: N-phenethylfluorenimine；N-(2-phenylethyl)-9H-fluoren-9-imine；N-(2-phenylethyl)fluoren-9-imine
• CAS: 119437-41-1
• 化学式: C₂₁H₁₇N
• 分子量: 283.373
• InChiKey: KEKHXRWKRPJMNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  12.4
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  fluorenone N-phenethylimine 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 为溶剂， -78.0 ℃ 、344.73 kPa 条件下， 反应 22.17h， 生成 芴
  参考文献：
  名称：

  Azophilic addition of alkyllithium reagents to fluorenimines. The synthesis of secondary amines

  摘要：

  DOI：

  10.1021/jo00270a034
• 作为产物：
  描述：

  芴 、 2-苯乙胺 在 [Cl₂NN]Cu 二叔丁基过氧化物 作用下， 以17%的产率得到fluorenone N-phenethylimine
  参考文献：
  名称：

  Transition Metal-Catalyzed C-H Amination Using Unactivated Amines

  摘要：

  发明的一个方面涉及一种动画或酰胺化方法，包括将包含反应性C—H键的底物与包含反应性N—H键的胺或酰胺，在氧化剂和含金属催化剂的存在下结合，从而形成具有反应性C—H键的碳与反应性N—H键的氮之间的共价键的产物。

  公开号：

  US20110213146A1

文献信息

• Monofluoro-substituted azomethine ylides in fluorocarbene reactions with imines. Synthesis and transformations of monofluoroaziridines
  作者：A. S. Konev、M. S. Novikov、A. F. Khlebnikov

  DOI：10.1134/s1070428007020224

  日期：2007.2

  N-Arylmethylene and N-benzhydrylideneamines react with fluorocarbene yielding fluoro-substituted azomethine ylides that undergo 1,3-pi-cyclization into aziridines. Generation of fluoroylides in the presence of dipolarophiles (dimethyl maleate or dirnethyl acetylenedicarboxylate) led to the reaction of 1,3-dipolar cycloaddition resulting in substituted 2-pyrrolines or pyrroles. 2-Fluoroaziridines, products of N-alkyl-N-benzhydrylideneamines 1,3-pi-cyclization, in the presence of acid catalysts suffer isomerization into alpha-fluoroimines and 1,3-disubstituted indoles.
• 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.
• DAI, WEI;SRINIVASAN, RAJGOPAL;KATZENELLENBOGEN, JOHN A., J. ORG. CHEM., 54,(1989) N, C. 2204-2208
  作者：DAI, WEI、SRINIVASAN, RAJGOPAL、KATZENELLENBOGEN, JOHN A.

  DOI：——

  日期：——