(2-cyanophenoxy)acetonitrile | 49615-99-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (2-cyanophenoxy)acetonitrile
• 英文别名: 2-(cyanomethoxy)benzonitrile；2-cyanomethoxybenzonitrile；2-cyanophenoxyacetonitrile；o-Cyanphenyl-cyanmethylaether；2-Cyanophenoxyacetonitril
• CAS: 49615-99-8
• 化学式: C₉H₆N₂O
• mdl: MFCD02257543
• 分子量: 158.159
• InChiKey: HCNYAOKYHQWSMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  56.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2-cyanophenoxy)acetonitrile 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以65%的产率得到3-氨基-1-苯甲呋喃-2-甲腈
  参考文献：
  名称：

  具有半胱氨酰白三烯2受体拮抗活性的3-乙酰乙酰氨基苯并[b]呋喃衍生物的合成。

  摘要：

  从3-氨基苯并[b]呋喃开始，合成了在3-位具有修饰的三烯系统的新型3-乙酰乙酰氨基苯并[b]呋喃衍生物。由于3-烯丙基乙酰氨基苯并[b]呋喃之间形成氢键，因此作为稳定异构体获得了3-乙酰基乙酰氨基苯并[b]呋喃的烯醇异构体3-[（3-羟基丁-2-烯丙基）氨基]苯并[b]呋喃。羟基和酰胺羰基。通过C-3侧链的C-2取代基的平面性表明烯醇化合物中存在改性的共轭三烯系统。评估了半胱氨酸白三烯1和2受体对这些化合物的拮抗活性。2-（4-氰基苯甲酰基或乙氧基羰基）-3-[（2-氰基-3-羟基丁-2-烯丙基）氨基]苯并[b]呋喃（，）具有中等活性。

  DOI：

  10.1039/b312682j
• 作为产物：
  描述：

  邻羟基苯甲腈 、 氯乙腈 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以88%的产率得到(2-cyanophenoxy)acetonitrile
  参考文献：
  名称：

  在实验和理论方法中，苯并呋喃部分制备的 Fe3+ 离子的高选择性和灵敏“开-关”荧光化学传感器

  摘要：

  开发并合成了一种基于苯并呋喃甘氨酰胺的化学传感器 3-(2-([4-fluorobenzyl]amino)acetamido)benzofuran-2-carboxamide ( BGA )，用于选择性和灵敏地检测 Fe 3+离子。使用紫外-可见光吸收和荧光分光光度计研究了探针BGA的光物理性质。在 DMSO/H 2中存在其他金属离子的情况下，化学传感器BGA对 Fe 3+离子显示出显着的“开-关”荧光响应O 溶液 (9/1, v/v)。使用紫外-可见光吸收和荧光分光光度计分别计算出极​​低的检测限 (LOD) 为 10 nM 和 43 nM。Job 的绘图分析揭示了BGA -Fe 3+配合物的形成，其结合化学计量比为 1:1，使用紫外-可见光光谱。还使用密度泛函理论计算证明了传感机制。

  DOI：

  10.1002/bio.4258

文献信息

• Polycyclic<i>N</i>-hetero compounds.<b>XXXIV</b>. Syntheses and evaluation of antidepressive activity of benzofuro-[2,3-<i>e</i>]imidazo[1,2-<i>c</i>]pyrimidines and their precursors
  作者：Takashi Hirota、Kenji Sasaki、Yohsuke Tashima、Taiji Nakayama

  DOI：10.1002/jhet.5570280210

  日期：1991.2

  Syntheses of 2,3-dihydrobenzofuro[2,3-e]imidazo[1,2-c]pyrimidine and its 5-substituted derivatives, corresponding to B-nor-6-oxa-11,13,15-triazasteroids, are described. These products and their precursors were screened to evaluate the antidepressive activity.

  描述了对应于B-nor-6-oxa-11,13,15-三氮杂甾体的2,3-二氢苯并呋喃[2,3- e ]咪唑并[1,2- c ]嘧啶及其5-取代衍生物的合成。筛选了这些产物及其前体以评估抗抑郁活性。
• A benzofuran-β-alaninamide based “turn-on” fluorescent chemosensor for selective recognition of Fe³⁺ ions
  作者：P. Madhu、P. Sivakumar、Rajendran Sribalan

  DOI：10.1039/c9nj02655j

  日期：——

  benzofuran-β-alaninamide based chemosensor, 3-(3-((4-methylbenzyl)amino)propanamido)benzofuran-2-carboxamide (BAA), was designed and synthesized for selective detection of Fe3+ ions. The binding ability of BAA towards Fe3+ in DMSO/H2O solution (9/1, v/v) has been studied by UV-vis absorption and fluorescence spectroscopy. Interestingly, the probe BAA exhibits an excellent “turn-on” fluorescence enhancement

  设计并合成了基于苯并呋喃-β-丙氨酰胺的化学传感器3-（3-（（（4-甲基苄基）氨基）丙酰胺基）苯并呋喃-2-羧酰胺（BAA），用于选择性检测Fe 3+离子。通过紫外可见吸收和荧光光谱研究了BAA对DMSO / H 2 O溶液（9/1，v / v）中Fe 3+的结合能力。有趣的是，探针BAA在424 nm处具有290 nm的激发波长，具有出色的“开启”荧光增强效果。BAA的量子产率确定为0.248铁配合物为0.447。通过UV-vis吸收法和荧光法分别将检出限（LOD）计算为1.3μM和0.067μM。这些值远低于美国环境保护局的饮用水准则（5.37μM）。Job的曲线测量证明了BAA和Fe 3+之间形成的络合物的2：1结合化学计量。此外，通过密度泛函理论（DFT）研究证实了BAA与Fe 3+的结合相互作用。最后，实际样品分析证明探针BAA更适合于检测Fe 3+。
• Docking studies of benzylidene anabaseine interactions with α7 nicotinic acetylcholine receptor (nAChR) and acetylcholine binding proteins (AChBPs): Application to the design of related α7 selective ligands
  作者：David C. Kombo、Anatoly Mazurov、Kartik Tallapragada、Philip S. Hammond、Joseph Chewning、Terry A. Hauser、Montserrat Vasquez-Valdivieso、Daniel Yohannes、Todd T. Talley、Palmer Taylor、William S. Caldwell

  DOI：10.1016/j.ejmech.2011.09.033

  日期：2011.11

  AChBPs isolated from Lymnaea stagnalis (Ls), Aplysia californica (Ac) and Bulinus truncatus (Bt) have been extensively used as structural prototypes to understand the molecular mechanisms that underlie ligand-interactions with nAChRs [1]. Here, we describe docking studies on interactions of benzylidene anabaseine analogs with AChBPs and alpha 7 nAChR. Results reveal that docking of these compounds using Glide software accurately reproduces experimentally-observed binding modes of DMXBA and of its active metabolite, in the binding pocket of Ac. In addition to the well-known nicotinic pharmacophore (positive charge, hydrogen-bond acceptor, and hydrophobic aromatic groups), a hydrogen-bond donor feature contributes to binding of these compounds to Ac. Bt, and the alpha 7 nAChR. This is consistent with benzylidene anabaseine analogs with OH and NH2 functional groups showing the highest binding affinity of these congeners, and the position of the ligand shown in previous X-ray crystallographic studies of ligand-Ac complexes. In the predicted ligand-Ls complex, by contrast, the ligand OH group acts as hydrogen-bond acceptor. We have applied our structural findings to optimizing the design of novel spirodiazepine and spiroimidazoline quinuclidine series. Binding and functional studies revealed that these hydrogen-bond donor containing compounds exhibit improved affinity and selectivity for the alpha 7 nAChR subtype and demonstrate partial agonism. The gain in affinity is also due to conformational restriction, tighter hydrophobic enclosures, and stronger cation-pi interactions. The use of AChBPs structure as a surrogate to predict binding affinity to alpha 7 nAChR has also been investigated. On the whole, we found that molecular docking into Ls binding site generally scores better than when a alpha 7 homology model, Bt or Ac crystal structure is used. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Discovery of novel α7 nicotinic acetylcholine receptor ligands via pharmacophoric and docking studies of benzylidene anabaseine analogs
  作者：David C. Kombo、Anatoly A. Mazurov、Joseph Chewning、Philip S. Hammond、Kartik Tallapragada、Terry A. Hauser、Jason Speake、Daniel Yohannes、William S. Caldwell

  DOI：10.1016/j.bmcl.2011.11.090

  日期：2012.1

  Based on pharmacophore elucidation and docking studies on interactions of benzylidene anabaseine analogs with AChBPs and alpha 7 nAChR, novel spirodiazepine and spiroimidazoline quinuclidine series have been designed. Binding studies revealed that some of hydrogen-bond donor containing compounds exhibit improved affinity and selectivity for the alpha 7 nAChR subtype in comparison with most potent metabolite of GTS-21, 3-(4-hydroxy-2-methoxybenzylidene)-anabaseine. Hydrophobicity and rigidity of the ligand also contribute into its binding affinity. We also describe alternative pharmacophoric features equidistant from the carbonyl oxygen atom of the conserved Trp-148 of the principal face, which may be exploited to further design diverse focused libraries targeting the alpha 7 nAChR. (C) 2011 Elsevier Ltd. All rights reserved.
• HIROTA, TAKASHI;SASAKI, KENJI;TASHIMA, YOHSUKE;NAKAYAMA, TAIJI, J. HETEROCYCL. CHEM., 28,(1991) N, C. 263-267
  作者：HIROTA, TAKASHI、SASAKI, KENJI、TASHIMA, YOHSUKE、NAKAYAMA, TAIJI

  DOI：——

  日期：——