2-(2-Chlorophenyl)-2-formylacetonitrile | 75175-24-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(2-Chlorophenyl)-2-formylacetonitrile
• 英文别名: 2-(2-Chlorophenyl)-3-oxopropanenitrile；α-formyl-2-chlorobenzeneacetonitrile；2-(2-chloro-phenyl)-3-oxo-propionitrile；2-(2-Chlor-phenyl)-3-oxo-propionitril
• CAS: 75175-24-5
• 化学式: C₉H₆ClNO
• 分子量: 179.606
• InChiKey: OQJQMYYULSCEEE-UHFFFAOYSA-N

物化性质

• 熔点：
  118-120 °C
• 沸点：
  274.6±30.0 °C(Predicted)
• 密度：
  1.263±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2-Chlorophenyl)-2-formylacetonitrile 在 乙醇 、 sodium 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 151.5h， 生成
  参考文献：
  名称：

  Synthesis and molecular modeling of 1H-pyrrolopyrimidine-2,4-dione derivatives as ligands for the α1-adrenoceptors

  摘要：

  Three different series of 1H-pyrrolopyrimidine-2,4-dione derivatives were designed and synthesized as ligands for the alpha(1)-adrenergic receptors (alpha(1)-ARs). A microwave-assisted protocol was developed in order to improve purity and yields of some final products. The majority of the synthesized compounds, tested in binding assays, displayed alpha(1)-AR affinities in the nanomolar range. Highest affinity values were found in derivatives 10b and 10c (K-i = 1.4 nM for both) whereas compound 10e was endowed with the best profile in term of alpha(1)-AR affinity (K-i = 2.71 nM) coupled with high selectivity towards 5-HT1A receptors (K-i > 10,000). Molecular docking studies were performed on human alpha(1)-ARs and human 5-HT1A receptors in order to rationalize the observed experimental affinity and selectivity; these computational studies helped to clarify molecular requirements for the design of high-selective alpha(1)-adrenergic ligands. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.043
• 作为产物：
  描述：

  邻氯苯乙腈 、 甲酸乙酯 在 2-甲基-2-丁醇 、 sodium hydride 作用下， 以 甲苯 为溶剂， 反应 6.0h， 以54%的产率得到2-(2-Chlorophenyl)-2-formylacetonitrile
  参考文献：
  名称：

  Selleri; Bruni; Costanzo, Il Farmaco, 1995, vol. 50, # 10, p. 679 - 687

  摘要：

  DOI：

文献信息

• 2,4-Diaminopyrimidines as Antimalarials. III. 5-Aryl Derivatives
  作者：Peter B. Russell、George H. Hitchings

  DOI：10.1021/ja01152a060

  日期：1951.8
• Benzodiazepine receptor ligands
  作者：G. Guerrini、A. Costanzo、F. Bruni、G. Ciciani、S. Selleri、P. Gratteri、B. Costa、C. Martini、A. Lucacchini

  DOI：10.1016/s0014-827x(99)00044-0

  日期：1999.6

  A new series of 2- and/or 3-substituted pyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides and their 8-chloro derivatives were synthesized, and their benzodiazepine receptor (BZR) affinities were evaluated in vitro in comparison to lead compound 3-ethoxycarbonyl-8-chloropyrazolo[5,1-c][1,2,4]benzotriazine-5-oxide (29) [1,2]. None of the new compounds showed significant affinity for BZR. On the basis of a pharmacophore/receptor model suggested for lead compound 29, some hypotheses to explain the inactivity of new derivatives are discussed. (C) 1999 Elsevier Science S.A. All rights reserved.