prodan | 1218780-81-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: prodan
• 英文别名: 3-(dimethylamino)-8,9,10,11-tetrahydro-7H-cyclohepta[α]naphthalen-7-one；3-dimethylamino-8,9,10,11-tetrahydro-7H-cyclohepta[a]naphthalen-7-one；3-(Dimethylamino)-8,9,10,11-tetrahydro-7h-cyclohepta[a]naphthalen-7-one；3-(dimethylamino)-8,9,10,11-tetrahydrocyclohepta[a]naphthalen-7-one
• CAS: 1218780-81-4
• 化学式: C₁₇H₁₉NO
• 分子量: 253.344
• InChiKey: MYTPZMSTEIYAHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  1
• 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：

  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170 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

• 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.