1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one | 649553-59-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one
• 英文别名: 1-(4-Methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one；1-(4-methyl-2,3-dihydro-1H-benzo[f]quinolin-8-yl)propan-1-one
• CAS: 649553-59-3
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: LRNRMPHOYWBCCL-UHFFFAOYSA-N

物化性质

• 熔点：
  119-120 °C
• 沸点：
  433.4±25.0 °C(Predicted)
• 密度：
  1.104±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  β-环糊精 、 1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Local Solvent Acidities in β-Cyclodextrin Complexes with PRODAN Derivatives

  摘要：

  The local solvent acidities (SA scale) of six 6-carbonyl-2-aminonaphthalene derivatives as beta-cyclodextrin complexes in water are determined through fluorescence quenching. The local polarities (E-T(N) scale) are determined through the shift of the emission center-of-mass. The apparent SA values reflect the solvent structure surrounding the guest's carbonyl group, whereas the apparent E-T(N) values reveal the net polarity of the entire guest molecule. Comparison of these values affords greater insight into the structures of the host-guest complexes. Derivatives 1 and 5 show unusually large acidities, indicative of highly exposed carbonyl groups. The remaining compounds give emission intensities pointing to shielded carbonyl groups. In this study, PRODAN and its derivatives are functioning as dual channel sensors of their local environment.

  DOI：

  10.1021/jp400765x
• 作为产物：
  描述：

  8-bromo-4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-1-one 在 copper(I) bromide 作用下， 以 四氢呋喃 、 N,N-二甲基乙酰胺 为溶剂， 反应 25.0h， 生成 1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one
  参考文献：
  名称：

  Does PRODAN Possess a Planar or Twisted Charge-Transfer Excited State? Photophysical Properties of Two PRODAN Derivatives

  摘要：

  The synthesis and photochemical properties of 1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one (7) and 2,2-dimethyl-1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one (8) are reported. These compounds are models for PRODAN, 6-propionyl-2-(dimethylamino)naphthalene, where the dialkyl-amino group is forced to remain coplanar with the naphthalene ring. The Stokes shifts of 7 and 8 in various solvents are compared with those of PRODAN. The absorption and emission transitions are calculated by the AM1 semiempirical method employing a conductor-like screening model for solvent effects. The experimental and calculated solvatochroism of both model compounds are of the same magnitude as PRODAN, suggesting that all fluoresce from a planar ICT state.

  DOI：

  10.1021/jp036013r

文献信息

• Does PRODAN Possess a Planar or Twisted Charge-Transfer Excited State? Photophysical Properties of Two PRODAN Derivatives
  作者：Bethany C. Lobo、Christopher J. Abelt

  DOI：10.1021/jp036013r

  日期：2003.12.1

  The synthesis and photochemical properties of 1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one (7) and 2,2-dimethyl-1-(4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-8-yl)propan-1-one (8) are reported. These compounds are models for PRODAN, 6-propionyl-2-(dimethylamino)naphthalene, where the dialkyl-amino group is forced to remain coplanar with the naphthalene ring. The Stokes shifts of 7 and 8 in various solvents are compared with those of PRODAN. The absorption and emission transitions are calculated by the AM1 semiempirical method employing a conductor-like screening model for solvent effects. The experimental and calculated solvatochroism of both model compounds are of the same magnitude as PRODAN, suggesting that all fluoresce from a planar ICT state.
• Local Solvent Acidities in β-Cyclodextrin Complexes with PRODAN Derivatives
  作者：Hannah R. Naughton、Christopher J. Abelt

  DOI：10.1021/jp400765x

  日期：2013.3.28

  The local solvent acidities (SA scale) of six 6-carbonyl-2-aminonaphthalene derivatives as beta-cyclodextrin complexes in water are determined through fluorescence quenching. The local polarities (E-T(N) scale) are determined through the shift of the emission center-of-mass. The apparent SA values reflect the solvent structure surrounding the guest's carbonyl group, whereas the apparent E-T(N) values reveal the net polarity of the entire guest molecule. Comparison of these values affords greater insight into the structures of the host-guest complexes. Derivatives 1 and 5 show unusually large acidities, indicative of highly exposed carbonyl groups. The remaining compounds give emission intensities pointing to shielded carbonyl groups. In this study, PRODAN and its derivatives are functioning as dual channel sensors of their local environment.