3-<4-(dimethylamino)phenyl>-3-phenylcyclopentene | 137696-50-5

• 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: 3-<4-(dimethylamino)phenyl>-3-phenylcyclopentene
• 英文别名: N,N-dimethyl-4-(1-phenylcyclopent-2-en-1-yl)aniline
• CAS: 137696-50-5
• 化学式: C₁₉H₂₁N
• 分子量: 263.382
• InChiKey: AAKBRYQEKBSJDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-<4-(dimethylamino)phenyl>-3-phenylcyclopentene 在 四氧化锇 、 十二/十四烷基二甲基氧化胺 作用下， 以 水 、 丙酮 为溶剂， 反应 2.25h， 生成 (1R*,2S*,3R*)-3-<4-(N,N-dimethylamino)phenyl>-3-phenylcyclopentane-1,2-diol 、 (1S*,2R*,3R*)-3-<4-(N,N-dimethylamino)phenyl>-3-phenylcyclopentane-1,2-diol
  参考文献：
  名称：

  Evidence of stereoelectronic control in osmium-catalyzed cis-dihydroxylations of sterically unbiased 3,3-diarylcyclopentenes

  摘要：

  This study provides strong evidence for the stereoelectronic control of diastereoselectivity in the osmium tetraoxide-catalyzed cis-dihydroxylation of sterically unbiased 3-(4-X-phenyl)-3-phenylcyclopentenes 1 (X = NO2, Br, Cl, OCH3, N(CH3)2), producing diastereomeric cis-diols 2 in cis:trans ratios (diol relative to the substituted arene) varying from 70:30 to 36:64 as determined by H-1 NMR and C-13 NMR spectroscopy. The reactions were carried out at room temperature in an 8:1 acetone/water solvent system, utilizing trimethylamine N-oxide as the terminal oxidant. Structural assignments were made by 2D-NOE H-1 NMR spectroscopy, C-13 NMR spectroscopy, and X-ray crystallographic analysis. In all cases the addition occurred opposite the more electron-rich aromatic ring as predicted by Cieplak's theory for explaining stereoelectronic control. The observed ratios correspond to an overall energy difference of 1.1 kcal/mol. A Hammet plot of log (cis:trans) versus the sigma(p), parameter produced a linear relationship with a correlation coefficient of 0.97. An efficient synthesis of the diarylcyclopentenes is described. The diastereomeric diols, or derivatives thereof, were separable by preparatory thin-layer chromatography.

  DOI：

  10.1021/ja00029a029
• 作为产物：
  描述：

  3-<4-(trimethylammonio)phenyl>-3-phenylcyclopentenyl iodide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以44%的产率得到3-<4-(dimethylamino)phenyl>-3-phenylcyclopentene
  参考文献：
  名称：

  Evidence of stereoelectronic control in osmium-catalyzed cis-dihydroxylations of sterically unbiased 3,3-diarylcyclopentenes

  摘要：

  This study provides strong evidence for the stereoelectronic control of diastereoselectivity in the osmium tetraoxide-catalyzed cis-dihydroxylation of sterically unbiased 3-(4-X-phenyl)-3-phenylcyclopentenes 1 (X = NO2, Br, Cl, OCH3, N(CH3)2), producing diastereomeric cis-diols 2 in cis:trans ratios (diol relative to the substituted arene) varying from 70:30 to 36:64 as determined by H-1 NMR and C-13 NMR spectroscopy. The reactions were carried out at room temperature in an 8:1 acetone/water solvent system, utilizing trimethylamine N-oxide as the terminal oxidant. Structural assignments were made by 2D-NOE H-1 NMR spectroscopy, C-13 NMR spectroscopy, and X-ray crystallographic analysis. In all cases the addition occurred opposite the more electron-rich aromatic ring as predicted by Cieplak's theory for explaining stereoelectronic control. The observed ratios correspond to an overall energy difference of 1.1 kcal/mol. A Hammet plot of log (cis:trans) versus the sigma(p), parameter produced a linear relationship with a correlation coefficient of 0.97. An efficient synthesis of the diarylcyclopentenes is described. The diastereomeric diols, or derivatives thereof, were separable by preparatory thin-layer chromatography.

  DOI：

  10.1021/ja00029a029