prodan | 1218780-80-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: prodan
• 英文别名: 7-dimethylamino-3,4-dihydrophenanthren-1(2H)-one；7-(dimethylamino)-3,4-dihydro-2H-phenanthren-1-one
• CAS: 1218780-80-3
• 化学式: C₁₆H₁₇NO
• 分子量: 239.317
• InChiKey: SPSARVVKICZJPE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  prodan 、 β-环糊精 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 prodan
  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：

  在 polyphosphoric acid 作用下， 反应 0.33h， 以230 mg的产率得到prodan
  参考文献：
  名称：

  PRODAN 是否具有 O-TICT 激发态？两种约束导数的合成与性质

  摘要：

  7-(二甲氨基)-3,4-二氢菲-1(2H)-one ( 7 ) 和3-(二甲氨基)-8,9,10,11-四氢-7H-环庚烷[a]的合成及光物理性质naphthalen-7-one ( 8 ) 被报道。这些化合物具有控制羰基扭曲程度的环烷酮亚结构。在六元环7点的力的羰基共面与萘环，而在7元环8个诱导显著捻。两者都具有 PRODAN（6-丙酰基-2-（二甲氨基）萘，1）的亚结构。比较这些化合物与 PRODAN 和 2,2-二甲基-1-(4-甲基-1,2,3,4-四氢苯并[f]喹啉-8-基)丙烷-1-酮的光物理行为(3 ) 表明 PRODAN 可能从 PICT 激发态发射，而不是从 O-TICT 激发态发射。

  DOI：

  10.1021/jp1002808

文献信息

• Dicyanovinylnaphthalenes for neuroimaging of amyloids and relationships of electronic structures and geometries to binding affinities
  作者：Andrej Petrič、Scott A. Johnson、Hung V. Pham、Ying Li、Simon Čeh、Amalija Golobič、Eric D. Agdeppa、Gerald Timbol、Jie Liu、Gyochang Keum、Nagichettiar Satyamurthy、Vladimir Kepe、Kendall N. Houk、Jorge R. Barrio

  DOI：10.1073/pnas.1214134109

  日期：2012.10.9

  binding affinities. The extreme cases were a nonplanar analog t-butyl-FDDNP, which shows low binding affinity for Abeta aggregates (520 nM K(i)) in vitro and a nearly planar tricyclic analog cDDNP, which displayed the highest binding affinity (10 pM K(i)). Using a previously published X-ray crystallographic model of 1,1-dicyano-2-[6-(dimethylamino)naphthalen-2-yl]propene (DDNP) bound to an amyloidogenic

  正电子发射断层扫描 (PET) 探针 2-(1-[6-[(2-氟乙基)(甲基)氨基]-2-萘基]亚乙基) (FDDNP) 用于淀粉样蛋白-β 的无创脑成像。 Abeta) 和其他淀粉样蛋白聚集体存在于阿尔茨海默病和其他神经退行性疾病中。使用光谱和计算方法合成和表征了一系列 FDDNP 类似物。这些分子的结合亲和力已通过实验测量并通过使用计算模型进行解释。这些类似物是通过系统地修改 FDDNP 的供体和受体侧来创建的，以了解与 Abeta 聚合体的最佳结合的结构要求。FDDNP 及其类似物是中性的、环境敏感的、具有高偶极矩的荧光分子，正如它们的光谱特性和偶极矩计算所证明的那样。这些化合物的优选溶液状态构象与结合亲和力直接相关。极端情况是非平面类似物 t-丁基-FDDNP，其在体外对 Abeta 聚集体 (520 nM K(i)) 显示出低结合亲和力，而近乎平面的三环类似物 cDDNP，显示出最高结合亲和力
• Does PRODAN Possess an O-TICT Excited State? Synthesis and Properties of Two Constrained Derivatives
  作者：Renata K. Everett、H. A. Ashley Nguyen、Christopher J. Abelt

  DOI：10.1021/jp1002808

  日期：2010.4.15

  ne (8) are reported. These compounds possess a cycloalkanone substructure that controls the extent of twisting of the carbonyl group. The six-membered ring in 7 forces the carbonyl group to be coplanar with the naphthalene ring, whereas the seven-membered ring in 8 induces a significant twist. Both have the substructure of PRODAN (6-propionyl-2-(dimethylamino)naphthalene, 1). Comparing the photophysical

  7-(二甲氨基)-3,4-二氢菲-1(2H)-one ( 7 ) 和3-(二甲氨基)-8,9,10,11-四氢-7H-环庚烷[a]的合成及光物理性质naphthalen-7-one ( 8 ) 被报道。这些化合物具有控制羰基扭曲程度的环烷酮亚结构。在六元环7点的力的羰基共面与萘环，而在7元环8个诱导显著捻。两者都具有 PRODAN（6-丙酰基-2-（二甲氨基）萘，1）的亚结构。比较这些化合物与 PRODAN 和 2,2-二甲基-1-(4-甲基-1,2,3,4-四氢苯并[f]喹啉-8-基)丙烷-1-酮的光物理行为(3 ) 表明 PRODAN 可能从 PICT 激发态发射，而不是从 O-TICT 激发态发射。
• 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.