4-nitro-7-(pyrrolidin-1-yl)benzo[c][1,2,5]oxadiazole | 74392-02-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶二唑类
• 英文名称: 4-nitro-7-(pyrrolidin-1-yl)benzo[c][1,2,5]oxadiazole
• 英文别名: 4-nitro-7-pyrrolidin-1-yl-benzo[1,2,5]oxadiazole；7-nitro-4-(pyrrolidin-1-yl)-2,1,3-benzoxadiazole；4-(N-Pyrrolidyl)-7-nitrobenz-2,1,3-oxadiazol；4-nitro-7-tetrahydro-1H-pyrrol-1-yl-2,1,3-benzoxadiazole；4-nitro-7 (pyrrolidin-1-yl)benzo[c][1,2,5]oxadiazole；4-Nitro-7-pyrrolidin-1-yl-2,1,3-benzoxadiazole
• CAS: 74392-02-2
• 化学式: C₁₀H₁₀N₄O₃
• mdl: MFCD00816681
• 分子量: 234.214
• InChiKey: KVFXCHFZIJJFCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  88
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-nitro-7-(pyrrolidin-1-yl)benzo[c][1,2,5]oxadiazole 在 sodium sulfite 作用下， 以 水 、 二甲基亚砜 为溶剂， 生成 4-aci-Nitro-7-pyrrolidin-1-yl-4,5-dihydro-benzo[1,2,5]oxadiazole-5-sulfonic acid anion
  参考文献：
  名称：

  7-氨基取代基对4-硝基苯并呋喃与亲核试剂反应性的显着影响

  摘要：

  已用亚硫酸根离子检测了在 7 位被 (a) N-乙基、(b) N-丁基、(c) 哌啶基或 (d) 吡咯烷基取代的四种 4-硝基苯并呋喃 (4a??4d) 的反应和水中的氢氧根离子??DMSO (80:20, v/v)。在第 5 位加入亚硫酸盐会得到平衡常数为 ca 的 σ 加合物。105 比从 4-硝基苯并呋喃形成相应加合物时低。这些减少归因于通过 4 和 7 取代基之间的共轭相互作用稳定了母体分子 4a??4d。在碱性溶液中，4a 和 4b 产生共轭碱，而 4c 和 4d 发生亲核取代，得到 7-羟基-4-硝基苯并呋喃。由于底物的亚胺离子特性，这里的反应性相对较高。关键词: 苯并呋喃, σ 加合物,

  DOI：

  10.1139/v05-116
• 作为产物：
  描述：

  4-aci-Nitro-7-pyrrolidin-1-yl-4,5-dihydro-benzo[1,2,5]oxadiazole-5-sulfonic acid anion 以 水 、 二甲基亚砜 为溶剂， 生成 4-nitro-7-(pyrrolidin-1-yl)benzo[c][1,2,5]oxadiazole
  参考文献：
  名称：

  7-氨基取代基对4-硝基苯并呋喃与亲核试剂反应性的显着影响

  摘要：

  已用亚硫酸根离子检测了在 7 位被 (a) N-乙基、(b) N-丁基、(c) 哌啶基或 (d) 吡咯烷基取代的四种 4-硝基苯并呋喃 (4a??4d) 的反应和水中的氢氧根离子??DMSO (80:20, v/v)。在第 5 位加入亚硫酸盐会得到平衡常数为 ca 的 σ 加合物。105 比从 4-硝基苯并呋喃形成相应加合物时低。这些减少归因于通过 4 和 7 取代基之间的共轭相互作用稳定了母体分子 4a??4d。在碱性溶液中，4a 和 4b 产生共轭碱，而 4c 和 4d 发生亲核取代，得到 7-羟基-4-硝基苯并呋喃。由于底物的亚胺离子特性，这里的反应性相对较高。关键词: 苯并呋喃, σ 加合物,

  DOI：

  10.1139/v05-116

文献信息

• A General Strategy to Enhance Donor‐Acceptor Molecules Using Solvent‐Excluding Substituents
  作者：Conner A. Hoelzel、Hang Hu、Charles H. Wolstenholme、Basel A. Karim、Kyle T. Munson、Kwan Ho Jung、Han Zhang、Yu Liu、Hemant P. Yennawar、John B. Asbury、Xiaosong Li、Xin Zhang

  DOI：10.1002/anie.201915744

  日期：2020.3.16

  β-carbonyl substituent creates a structural buffer between the donor and the surrounding solvent. Through computational and experimental analyses, it is demonstrated that the β-carbonyl simultaneously attenuates two distinct solvent-dependent quenching mechanisms. Using the β-carbonyl substituent, improvements in the photophysical properties of commonly used D-A fluorophores and their enhanced performance

  尽管有机供体-受体（DA）分子广泛应用于多个领域，但由于固有的极性敏感性会抑制光化学过程，因此可能会限制更多DA分子的应用。本文介绍了一种简便的化学修饰方法，可通过添加基于β-羰基的极性取代基来减弱溶剂依赖的激发态猝灭机理。结果揭示了一种机制，其中β-羰基取代基在供体和周围溶剂之间产生结构缓冲。通过计算和实验分析，证明了β-羰基同时减弱了两种不同的溶剂依赖性猝灭机理。使用β-羰基取代基
• Method and Means Relating to Multiple Herbicide Resistance in Plants
  申请人：Cummins Ian

  公开号：US20100184601A1

  公开（公告）日：2010-07-22

  Methods for overcoming multiple herbicide resistance (MHR) in plants using inhibitors of GST suppression of Formula (I), novel chemical inhibitors of Formula (Ia), compositions comprising compounds of Formula (I), and uses and methods relating thereto.

  使用公式(I)的GST抑制剂、公式(Ia)的新型化学抑制剂、含有公式(I)化合物的组合物以及与之相关的用途和方法，来克服植物中的多重除草剂抗性(MHR)的方法。
• Heberer, H.; Kersting, H.; Matschiner, H., Journal fur praktische Chemie (Leipzig 1954), 1985, vol. 327, # 3, p. 487 - 504
  作者：Heberer, H.、Kersting, H.、Matschiner, H.

  DOI：——

  日期：——
• Pyrene-Excimers-Based Antenna Systems
  作者：Stefano Cicchi、Pierangelo Fabbrizzi、Giacomo Ghini、Alberto Brandi、Paolo Foggi、Agnese Marcelli、Roberto Righini、Chiara Botta

  DOI：10.1002/chem.200801379

  日期：2009.1.5

  AbstractA series of dendrimeric compounds bearing pyrene units were synthesized to afford light‐harvesting antennae based on the formation of intramolecular excimers. The synthetic plan profited from the efficiency of the Huisgen reaction, the 1,3‐dipolar cycloaddition of azides and terminal alkynes, which allowed ready assembly of the different building blocks. The three molecular antennae obtained, of increasing generation, revealed efficient energy transfer both in solution and in the solid state.
• Photophysical and Dynamic NMR Studies on 4-Amino-7-nitrobenz-2-oxa-1, 3-diazole Derivatives:  Elucidation of the Nonradiative Deactivation Pathway
  作者：Satyen Saha、Anunay Samanta

  DOI：10.1021/jp982154v

  日期：1998.10.1

  A series of 4-aminonitrobenzoxadiazole (NBD) derivatives in which the amino nitrogen is part of a four- to seven-membered heterocyclic ring and a second series of 4-dialkylamino NBD derivatives with different alkyl chain lengths have been prepared and fully characterized and their photophysical properties investigated in an attempt to find out the nonradiative deactivation pathway of the fluorescent state in these systems. It is observed that the fluorescence properties of the NBD derivatives are highly sensitive to the structure of the amino moiety and the polarity of the surrounding media. It is shown that the nonradiative rate constants for the derivatives with large alkyl groups and large ring systems are considerably higher than those for systems with smaller alkyl groups and smaller ring systems. Dynamic NMR experiments have been carried out to probe the internal motion in the systems. The internal rotation around the bond connecting the amino nitrogen and the NBD ring is found to be rather slow in the ground state. The rate for the internal rotation is found to be the highest for the six-membered ring, and this has been interpreted in terms of the partial double bond character of the C-N bond. The results of the experiments seem to indicate that inversion of the amino nitrogen plays the most important role in determining the fluorescence efficiency of the systems.