3-[(6-溴萘-2-基)甲基氨基]丙酸 | 649553-61-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: 3-[(6-溴萘-2-基)甲基氨基]丙酸
• 英文名称: 3-[(6-bromonaphthalen-2-yl)methylamino]propionic acid
• 英文别名: 3-[(6-Bromonaphthalen-2-yl)-methylamino]propanoic acid；3-[(6-bromonaphthalen-2-yl)-methylamino]propanoic acid
• CAS: 649553-61-7
• 化学式: C₁₄H₁₄BrNO₂
• 分子量: 308.175
• InChiKey: ZLTYGCUOUOIBRX-UHFFFAOYSA-N

物化性质

• 沸点：
  490.4±30.0 °C(Predicted)
• 密度：
  1.500±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-[(6-溴萘-2-基)甲基氨基]丙酸 在 氢氧化钾 、 PPA 、 一水合肼 作用下， 以 N,N-二甲基乙酰胺 、 二乙二醇 为溶剂， 反应 4.0h， 生成 8-bromo-4-methyl-1,2,3,4-tetrahydrobenzo[f]quinolin-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
• 作为产物：
  描述：

  丙烯酸 、 6-bromo-N-methyl-2-naphthylamine 在 溶剂黄146 作用下， 反应 1.0h， 以96%的产率得到3-[(6-溴萘-2-基)甲基氨基]丙酸
  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.