2,6-二氰基-3-三氟甲基-5-苯基苯胺 | 86439-16-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,6-二氰基-3-三氟甲基-5-苯基苯胺
• 中文别名: 2,6-二氰基-3-(三氟甲基)-5-苯胺
• 英文名称: 2,6-dicyano-3-trifluoromethyl-5-phenylaniline
• 英文别名: 2-amino-4-phenyl-6-(trifluoromethyl)benzene-1,3-dicarbonitrile
• CAS: 86439-16-9
• 化学式: C₁₅H₈F₃N₃
• 分子量: 287.244
• InChiKey: XKAMTIXYJPUNMB-UHFFFAOYSA-N

物化性质

• 熔点：
  168 °C
• 沸点：
  466.5±45.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  73.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,6-二氰基-3-三氟甲基-5-苯基苯胺 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 3-amino-4-trifluoromethyl-6-phenylindazole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel pyrimido[1,2-b]indazoles as potential anticancer agents against A-549 cell lines

  摘要：

  A series of novel pyrimido[1,2-b]indazoles 5, 7 have been prepared from 3-trifluoromethyl-5-phenyl-2,6-dicyano anilines 1 via novel indazole regioisomers 3 and 4 through a facile strategy. Specific examples were evaluated for anticancer activity in vitro and found to exhibit promising activity against A-549 cell lines and are more effective than Etoposide. QSAR models were developed and validated by cross-validation method. The results of the best QSAR model were further compared with the crystal structure of tubulin protein. The binding energies estimated were found to have a good correlation with the experimental inhibitory potencies. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.087
• 作为产物：
  描述：

  苯甲酰三氟丙酮 、 丙二腈 以75%的产率得到
  参考文献：
  名称：

  GUDRINIETSE, EH. YU.;GUTTSAJT, A. V.;BELYAKOV, S. V.;FOMIN, A. N., IZV. AN LATVSSR. CEP. XIM., 1983, N 2, 245-246

  摘要：

  DOI：

文献信息

• Synthesis and adenosine receptors binding studies of new fluorinated analogues of pyrido[2,3-d]pyrimidines and quinazolines
  作者：Balakumar Chandrasekaran、Pran Kishore Deb、Sonja Kachler、Raghuram Rao Akkinepalli、Raghuprasad Mailavaram、Karl-Norbert Klotz

  DOI：10.1007/s00044-017-2099-z

  日期：2018.3

  A series of new fluorine containing pyrido[2,3-d]pyrimidines and imidazo[1,2-c]pyrido[3,2-e]pyrimidines along with a series of bioisosteric fluorinated quinazolines were synthesised following appropriate synthetic schemes and characterised by spectral analytical means. X-ray crystal structure of the key precursor 1 (2-amino-3-cyano-4-trifluoro-methyl-6-phenyl-pyridine) was also determined to gain insight

  按照适当的合成方案，合成了一系列新的含氟吡啶并[2,3- d ]嘧啶和咪唑并[1,2- c ]吡啶基[3,2- e ]嘧啶以及一系列生物等位氟化的喹唑啉，并进行了表征光谱分析手段。还确定了关键前体1（2-氨基-3-氰基-4-三氟-甲基-6-苯基吡啶）的X射线晶体结构，以了解其反应活性。所有化合物对腺苷受体（ARs）的结合亲和力数据表明，在2和4位（2a）具有游离氨基（NH 2）基的吡啶并[2,3- d ]嘧啶骨架显示出对hA的最大结合亲和力3对hA 1具有相似的亲和力，而对hA 2A AR具有较低的亲和力，导致化合物相对于A 1没有A 3选择性，相对于A 2A AR没有中等选择性（K i hA 1  = 0.62 µM，hA 2A  = 3.59 µM和hA 3  = 0.42 µM）。有趣的是，两个氨基都被羰基（C = O）（化合物4）取代导致对hA 1 AR的亲和力显着提高，但对hA 2A和hA
• Regioselective addition of Grignard reagents to 2,6-dicyanoanilines and cyclization to new quinazoline derivatives under thermal/microwave irradiation conditions
  作者：D. Maitraie、T. Yakaiah、K. Srinivas、G. Venkat Reddy、S. Ravikanth、B. Narsaiah、P. Shanthan Rao、K. Ravikumar、B. Sridhar

  DOI：10.1016/j.jfluchem.2006.01.003

  日期：2006.3

  with Grignard reagents gave imine regioisomers 4 and 5. Each imine regioisomer was separated and independently cyclized to give new quinazoline derivatives 6, 7 and 8, 9, respectively, under different microwave irradiation conditions.

  已经开发了两种合成新的喹唑啉衍生物的策略。2，6-二氰基苯胺与格氏试剂反应，然后环化，得到两个喹唑啉区域异构体2和3。交替地，与格氏试剂反应的2，6-二氰基苯胺产生亚胺区域异构体4和5。各区域异构体亚胺分离并独立地环化，得到新的喹唑啉衍生物6，7和8，9分别不同的微波照射的条件下。
• A simple and facile method for the synthesis of novel 5/7 trifluoromethyl-substituted 4(3H)-quinazolone regioisomers
  作者：D. Maitraie、G. Venkat Reddy、V.V.V.N.S. Rama Rao、S. Ravi Kanth、P. Shanthan Rao、B. Narsaiah

  DOI：10.1016/s0022-1139(02)00194-x

  日期：2002.12

  The unsymmetrical 1,3-diketones 1 on reaction with malononitrile is resulted an interesting trifunctional intermediates 2 and 3. The intermediate 2 is hydrolyzed to give 2,6-dicarboxamido aniline 4 which on cyclisation gave two regioisomers of 1,2-dihydro-4(3H)quinazolinones 5 and 6. The effect of substituents on compound 4 is characteristic for formation of regioisomers in different proportions. Each regioisomer on dehydrogenation under mild condition using active MnO2 gave corresponding 4(3H)-quinazolones 7 and 8, respectively. (C) 2002 Elsevier Science B.V. All rights reserved.
• Synthesis, anti-inflammatory evaluation and docking studies of some new fluorinated fused quinazolines
  作者：C. Balakumar、P. Lamba、D. Pran Kishore、B. Lakshmi Narayana、K. Venkat Rao、K. Rajwinder、A. Raghuram Rao、B. Shireesha、B. Narsaiah

  DOI：10.1016/j.ejmech.2010.07.063

  日期：2010.11

  A series of novel 8/10-trifluoromethyl-substituted-imidazo[1,2-c] quinazolines have been synthesized and evaluated in vivo (rat paw edema) for their anti-inflammatory activity and in silico (docking studies) to recognize the hypothetical binding motif of the title compounds with the cyclooxygenase isoenzymes (COX-1 and COX-2) employing GOLD (CCDC, 4.0.1 version) software. The compounds, 9b and 10b, were found to have good anti-inflammatory activity [around 80% of the standard: indomethacin]. The binding mode of the title compounds has been proposed based on the docking studies. Crown Copyright (C) 2010 Published by Elsevier Masson SAS. All rights reserved.
• Rodinovskaya, L. A.; Sharanin, Yu. A.; Litvinov, V. P., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 11, p. 2230 - 2235
  作者：Rodinovskaya, L. A.、Sharanin, Yu. A.、Litvinov, V. P.、Shestopalov, A. M.、Promonenkov, V. K.、et al.

  DOI：——

  日期：——