2,5-dimethoxy-4-(pyrrolidin-1-yl)benzaldehyde | 692775-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 2,5-dimethoxy-4-(pyrrolidin-1-yl)benzaldehyde
• 英文别名: 2,5-Dimethoxy-4-pyrrolidin-1-yl-benzaldehyde；2,5-dimethoxy-4-pyrrolidin-1-ylbenzaldehyde
• CAS: 692775-87-4
• 化学式: C₁₃H₁₇NO₃
• mdl: MFCD03995331
• 分子量: 235.283
• InChiKey: PVYKEKQDQZMXCB-UHFFFAOYSA-N

物化性质

• 溶解度：
  >35.3 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2,5-dimethoxy-4-(pyrrolidin-1-yl)benzaldehyde 在 正丁基锂 、 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 4,4'-bis(4-(2,5-dimethoxy-4-(pyrrolidin-1-yl)styryl)styryl)-2,2'-bipyridine
  参考文献：
  名称：

  D-π-A-A-π-D Prototype 2,2′-Bipyridine Dyads Exhibiting Large Structure and Environment-Sensitive Fluorescence: Synthesis, Photophysics, and Computation

  摘要：

  A series of 4,4'-pi-conjugated-2,2'-bipyridine chromophores (MS 1-8) were synthesized, and their photo-physical and thermal properties were investigated. The title "push-pull' chromophores", except MS 1, were integrated with both alkoxy and alkylamino donor functionalities that differ in their donation capabilities. The oligophenylenevinylene (OPV) chromophores MS 4-8 are associated with a pi-extended backbone in which the position and the number of alkoxy donors were systematically varied. All of the studied systems possess a D-pi-A-A-pi-D dyad archetype in which the A-A is the central 2,2'-bipyridine acceptor core that is electronically attached with the donor termini through pi-linkers. The fluorescence quantum yields of the synthesized chromophores are found to be sensitive to the molecular archetype and the solvent medium. Out of the eight fluorescent compounds reported in this article, the compound MS 5 exhibits fluorescence in the solid state also. The modulating effect of the nature, position, and number of donor functionalities on the optical properties of these classes of compounds has further been comprehended on the basis of DFT and TD-DFT computation in a solvent reaction field.

  DOI：

  10.1021/jo202015m
• 作为产物：
  描述：

  2,5-二甲氧基苯胺 在 potassium carbonate 、 三氯氧磷 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 2,5-dimethoxy-4-(pyrrolidin-1-yl)benzaldehyde
  参考文献：
  名称：

  不对称取代和π共轭的2,2'-联吡啶衍生物：合成，光谱，计算和晶体学

  摘要：

  一系列新的单取代的苯乙烯基和双苯乙烯基-2,2'-联吡啶发光体（化合物16 – 23）是通过霍纳-沃兹沃思-埃蒙斯反应合成的，涉及单膦酸酯和给体芳族醛。在标题发色团中，氨基供体在无环和环状之间变化，而烷氧基供体的数目和位置不同。这些生色团的吸收最大值主要是由于不同供体和受体部分之间的分子内电荷转移（ICT）引起的。标题供体-受体分子在室温下的溶液中表现出强烈的荧光，并且发现其发射行为对溶剂极性高度敏感。所有的发色团的荧光光谱和量子产率被记录在四个不同的溶剂介质，以及发色团16，17，19，和21也表现出固态荧光。供体官能团的性质和位置的在标题的发色团（电子吸收特性的联吡啶基部分的共轭主链的影响16 - 23）已被证实，其还进一步由DFT和TD-DFT计算证实这两种在气相和溶液相中。化合物的晶体结构18已被描述为家庭（代表构件16 - 23）。

  DOI：

  10.1021/acs.joc.5b02345

文献信息

• Asymmetrically Substituted and π-Conjugated 2,2′-Bipyridine Derivatives: Synthesis, Spectroscopy, Computation, and Crystallography
  作者：Ramakrishna Bodapati、Monima Sarma、Arunkumar Kanakati、Samar K. Das

  DOI：10.1021/acs.joc.5b02345

  日期：2015.12.18

  A new series of monosubstituted styryl- and bistyryl-2,2′-bipyridine luminophores (compounds 16–23) have been synthesized via Horner–Wadsworth–Emmons reaction involving a monophosphonate and donor aromatic aldehydes. In the title chromophores, the amino donors are varied between acyclic and cyclic while the alkoxy donors are varied in terms of their number and position. The absorption maxima of these

  一系列新的单取代的苯乙烯基和双苯乙烯基-2,2'-联吡啶发光体（化合物16 – 23）是通过霍纳-沃兹沃思-埃蒙斯反应合成的，涉及单膦酸酯和给体芳族醛。在标题发色团中，氨基供体在无环和环状之间变化，而烷氧基供体的数目和位置不同。这些生色团的吸收最大值主要是由于不同供体和受体部分之间的分子内电荷转移（ICT）引起的。标题供体-受体分子在室温下的溶液中表现出强烈的荧光，并且发现其发射行为对溶剂极性高度敏感。所有的发色团的荧光光谱和量子产率被记录在四个不同的溶剂介质，以及发色团16，17，19，和21也表现出固态荧光。供体官能团的性质和位置的在标题的发色团（电子吸收特性的联吡啶基部分的共轭主链的影响16 - 23）已被证实，其还进一步由DFT和TD-DFT计算证实这两种在气相和溶液相中。化合物的晶体结构18已被描述为家庭（代表构件16 - 23）。
• D-π-A-A-π-D Prototype 2,2′-Bipyridine Dyads Exhibiting Large Structure and Environment-Sensitive Fluorescence: Synthesis, Photophysics, and Computation
  作者：Monima Sarma、Tanmay Chatterjee、Susanta Ghanta、Samar K. Das

  DOI：10.1021/jo202015m

  日期：2012.1.6

  A series of 4,4'-pi-conjugated-2,2'-bipyridine chromophores (MS 1-8) were synthesized, and their photo-physical and thermal properties were investigated. The title "push-pull' chromophores", except MS 1, were integrated with both alkoxy and alkylamino donor functionalities that differ in their donation capabilities. The oligophenylenevinylene (OPV) chromophores MS 4-8 are associated with a pi-extended backbone in which the position and the number of alkoxy donors were systematically varied. All of the studied systems possess a D-pi-A-A-pi-D dyad archetype in which the A-A is the central 2,2'-bipyridine acceptor core that is electronically attached with the donor termini through pi-linkers. The fluorescence quantum yields of the synthesized chromophores are found to be sensitive to the molecular archetype and the solvent medium. Out of the eight fluorescent compounds reported in this article, the compound MS 5 exhibits fluorescence in the solid state also. The modulating effect of the nature, position, and number of donor functionalities on the optical properties of these classes of compounds has further been comprehended on the basis of DFT and TD-DFT computation in a solvent reaction field.