(E)-6-(2-(4-(dimethylamino)phenyl)ethenyl)fulvene

• 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: (E)-6-(2-(4-(dimethylamino)phenyl)ethenyl)fulvene
• 英文别名: 4-[(E)-3-cyclopenta-2,4-dien-1-ylideneprop-1-enyl]-N,N-dimethylaniline
• 化学式: C₁₆H₁₇N
• 分子量: 223.318
• InChiKey: YWLSTPBOSBLERS-WEVVVXLNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  3-(4-dimethylamino-phenyl)-propenal 、 环戊二烯 在 sodium 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以6%的产率得到(E)-6-(2-(4-(dimethylamino)phenyl)ethenyl)fulvene
  参考文献：
  名称：

  Structural Effects of C₆ Substitution in 6-(4-(Dimethylamino)phenyl)fulvenes

  摘要：

  The single-crystal X-ray structures of 6-(4-(dimethylamino)phenyl)-6-methylfulvene (2) and of two polymorphs of 6-(4-(dimethylamino)phenyl)-6-phenylfulvene (3(P2(1)/c) and 3(Pca2(1))) have been determined and the structures of a series of 6-arylfulvenes (1-8) have been optimized at the HF/6-31G level. Analysis of these structures reveals how resonance and crystal lattice effects influence the degree of coplanarity between the aryl and fulvene rings. The torsional angles at the aryl-fulvene bonds are significantly larger in the optimized structures than in the X-ray structures. Natural bond orbital pi charges and dipole moments calculated for the X-ray and optimized structures show that the crystalline environment enhances molecular polarization. Qualitative responses for second harmonic generation in powder samples have been observed in 2, 3(Pca2(1)), and 5. Compounds 2 and 3(Pca2(1)) have similar packing motifs despite packing in different space groups.

  DOI：

  10.1021/jo990931x

文献信息

• Structural Effects of C₆ Substitution in 6-(4-(Dimethylamino)phenyl)fulvenes
  作者：Matthew L. Peterson、Jeffrey T. Strnad、Thomas P. Markotan、Carl A. Morales、Donald V. Scaltrito、Stuart W. Staley

  DOI：10.1021/jo990931x

  日期：1999.12.1

  The single-crystal X-ray structures of 6-(4-(dimethylamino)phenyl)-6-methylfulvene (2) and of two polymorphs of 6-(4-(dimethylamino)phenyl)-6-phenylfulvene (3(P2(1)/c) and 3(Pca2(1))) have been determined and the structures of a series of 6-arylfulvenes (1-8) have been optimized at the HF/6-31G level. Analysis of these structures reveals how resonance and crystal lattice effects influence the degree of coplanarity between the aryl and fulvene rings. The torsional angles at the aryl-fulvene bonds are significantly larger in the optimized structures than in the X-ray structures. Natural bond orbital pi charges and dipole moments calculated for the X-ray and optimized structures show that the crystalline environment enhances molecular polarization. Qualitative responses for second harmonic generation in powder samples have been observed in 2, 3(Pca2(1)), and 5. Compounds 2 and 3(Pca2(1)) have similar packing motifs despite packing in different space groups.